Patent
Atlas literature
Patent
US 10,899,711Patent drawings and their descriptions. Click a drawing to enlarge it.
FIG. 2B). In still yet other embodiments n is at least 2 such that a polybenzoquinline polybenzo q uinoline product may be formed. In some such embodiments the …
FIG. 3A, these species are merely exemplary. It will be understood that the synthesis scheme may be generalized by altering the nature of the aromatic …
FIG. 4B. In addition, although the R-group in the exemplary embodiment provided in
FIGS. 6 and 7, it should be understood that the R-group in accordance with embodiments may further comprise one or more par a-or meta- substituted …
FIGS. 8A, 8B and 9A, compounds 3b, 5b, 8 and 11 a) may be adapted to furnish substituted polybenzoquinolines (e.g.,
FIG. 9A) is slightly modified. In such embodiments the bifunctional monomer comprising the requisite alkyne and aldimine functional groups incorporates an …
FIGS. 18A to 18 D. As demonstrated, the modular nature of such functionalities allows for a wide- variety of substitution, including, for example, aromatic rin …
Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
1-48. Canceled
Canceled
A method of producing bi-quinolines or polyquinolines comprising: reactin q a bifunctional aromatic aldimine with an aromatic mono- or bialk vnv l in the presence of a Lewis acid mediator and an oxidant to produce the corresponding bi- q uinoline or pol yc uinoline, wherein: the bifunctional aromatic aldimine is of formula: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.1.svg 1.26 1.26 Black and white comprising: a first aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1. and the first aromatic core is optionally substituted with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; a first aldimine functionality immediately and covalentl y attached to the first aromatic core, wherein R₁ is an aromatic or heteroaromatic functionality optionally substituted with one or more substituents, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron donating functionality, or any combination thereof; and a second aldimine functionality immediatel y and covalent lv attached to the first aromatic core, wherein R₂ is one of the functionalities selected from the g roup of: R1, a substituted aromatic rin g, an [[or]] unsubstituted aromatic ring, a [[or]] substituted heteroaromatic ring, and an unsubstituted heteroaromatic rin g; and the aromatic mono- or bi alkynyl comprises a second aromatic core and one or two aromatic terminal alkyne functionalities respectivel y; and wherein the first and the second aldimine functionalities of the bifunctional aromatic aldimine react with the one or two aromatic terminal alkyne functionalities of the aromatic mono- or bi alkynyl to yield the corresponding bi-quinoline or polyquinoline[[s]] comprising quinoline moieties incorporating the nitrogens of the first and the second aldimine functionalities. Currently amended
The method of claim 49, wherein n is 2 such that the first aromatic core is a naphthyl and the q uinoline moieties are benzoquinoline. Currently amended
The method of claim 49, wherein n is 2 and the ring that does not bear the first aldimine functionality is heteroaromatic. Previously presented
The method of claim 49, wherein n is at least 2 and some or all of the aromatic rings of the first aromatic core are linked at the 4 and 6 positions rather than fused, such that the aromaticity of the first aromatic core is maintained. Previously presented
The method of claim 49, wherein the second aromatic core is a naphthyl moiety. Previously presented
The method of claim 49, wherein both the aromatic mono alkynyl comprising one aromatic terminal alkyne functionality and the aromatic bialkynyl comprising two aromatic alkyne functionalities are used in the same reaction mixture to control the length of the polyquinolines. Currently amended
50-52. Canceled
Canceled
Canceled
A method of forming nitrogen-doped aromatic molecular segments or graphene nanoribbons comprising: reactin g a bifunctional aromatic aldimine with an aromatic mono- or bialk yny l in the presence of a Lewis acid mediator and an oxidant to produce the correspondin g bi- q uinoline or pol vc uinoline, and formin g intramolecular C-C bonds between aromatic and heteroaromatic moieties of the correspondin g bi- q uinoline or po lyq uino l ine to form the correspondin g nitrogen- doped molecular se g ment or g raphene nanoribbon, wherein: the bifunctional aromatic aldimine is of formula: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.2.svg 1.26 1.26 Black and white comprising: a first aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1 s and the first aromatic core is optionally substituted at any of its aromatic or heteroaromatic rings with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; a first aldimine functionality immediately and covalentl y attached to the first aromatic core, wherein R₁ is an aromatic or heteroaromatic functionality optionally substituted with one or more substituents, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron donating functionality, or any combination thereof; and a second aldimine functionality immediately and covalentl y attached to the first aromatic core, wherein R₂ is one of the functionalities selected from the g roup of: R1, a substituted aromatic rin g, an [[or]] unsubstituted aromatic ring, a [[or]] substituted heteroaromatic ring, and an unsubstituted heteroaromatic rin g; and the aromatic mono- or bi alkynyl comprises a second aromatic core, and one or two aromatic terminal alkyne functionalities, respectivel y; and wherein the first and the second aldimine functionalities of the bifunctional aromatic aldimine react with the one or two aromatic terminal alkyne functionalities of the aromatic mono- or bi alkynyl to yield the corresponding bi-quinoline or polyquinoline[[s]] comprising quinoline moieties incorporating the nitrogens of the first and the second aldimine functionalities. Currently amended
The method of claim 62, wherein n is 1, the first aromatic core is a benzene additionally substituted with two C l functionalities at positions 2 and 5, the second aldimine functionality is located at position 4, the aromatic mono alkynyl is phenylacetylene, and two intramolecular C-C bonds are formed via Heck reaction fe such that the correspondin g nitro g en-doped molecular se g ment or g raphene nanoribbon is a rubicene nitrogen-doped molecular segment. Currently amended
The method of claim 62, wherein n is 1, the first aromatic core is a benzene additionally substituted with two C l functionalities at positions 2 and 5, the second aldimine functionality is located at position 4, the aromatic mono alkynyl is naphthyl alkyne, and two intramolecular C-C bonds are formed via base mediated cyclodehydrogenation reaction such that the correspondin g nitro g en-doped molecular se g ment or g raphene nanoribbon is a tetrabenzopentacene nitrogen-doped molecular segment. Currently amended
The method of claim 62, wherein the aromatic i alkynyl is 1,5-dichloro-9,1 0-diethynylanthracene, and intramolecular C-C bonds are formed via Heck reaction. Currently amended
The method of claim 62, wherein the aromatic i alkynyl is 1,5-dichloro-9,1 0-diethynylanthracene, and intramolecular C-C bonds are formed via base mediated cyclodehydrogenation reaction. Currently amended
67-74. Canceled
Canceled
A[[n]] bifunctional aromatic aldimine for producing quinolines, polyquinolines, nitrogen-doped aromatic molecular segments, and graphene nanoribbons according to: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.3.svg 1.4 1.33 Black and white and comprising: an aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1 s and the aromatic core is optionally substituted at any of its aromatic or heteroaromatic rings with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; an aldimine functionality immediately and covalently attached to the aromatic core, wherein R is a substituted or unsubstituted aromatic or heteroaromatic ring; and an aromatic terminal alkyne functionality immediately and covalently attached at any position of the aromatic core and capable of reacting with an aromatic aldimine in an aza-Diels Alder Povarov reaction. Currently amended
(Curren l ty Amended) The bifunctional aromatic aldimine of claim 75, wherein R is substituted with at least one functionality, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron donating functionality, or any combination thereof. Currently amended
The bifunctional aromatic aldimine of claim 75, wherein n is at least 2. Currently amended
The bifunctional aromatic aldimine of claim 75, wherein n is 2 and the ring that does not bear the aldimine functionality is heteroaromatic. Currently amended
The bifunctional aromatic aldimine of claim 75, wherein n is 2 and the ring that does not bear the aldimine functionality is further functionalized with at least one of: aliphatic group, electron withdrawing group, electron donating group. Currently amended
The bifunctional aromatic aldimine of claim 75, wherein n is at least 2 and some or all of the aromatic rings of the aromatic core are linked at the 4 and 6 positions rather than fused, such that the aromaticity of the aromatic core is maintained. Currently amended
A method of producing polyquinolines comprising: reactin g a bifunctional aromatic aldimine with itself in the presence of a Lewis acid mediator and an oxidant to produce the correspondin g po lyc uino l ine, wherein: the bifunctional aromatic aldimine is of formula: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.4.svg 1.35 1.07 Black and white comprising: an aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1, and the aromatic core is optionally substituted at any of its aromatic or heteroaromatic rings with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; an aldimine functionality immediately and covalentl y attached to the aromatic core, wherein R is an aromatic or heteroaromatic functionality optionally substituted with one or more substituents, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron donating functionality, or any combination thereof; and an aromatic terminal alkyne functionality immediately and covalentl y attached at any position of the aromatic core; and wherein the aldimine functionality of one molecule of the bifunctional aromatic aldimine reacts with the aromatic terminal alkyne functionality of another molecule of the bifunctional aromatic aldimine to yield the correspondin g polyquinoline[[s]] comprising quinoline moieties incorporating the nitrogens of the aldimine functionalities. Currently amended
The method of claim 82, wherein n is 2 such that the aromatic core is a naphthyl and the q uinoline moieties are benzoquinoline. Currently amended
The method of claim 82, wherein n is 2 and the ring that does not bear the aldimine functionality is heteroaromatic. Previously presented
The method of claim 82, wherein n is at least 2 and some or all of the aromatic rings of the aromatic core are linked at the 4 and 6 positions rather than fused, such that the aromaticity of the aromatic core is maintained. Previously presented
The method of claim 82, wherein n is at least 2 and any ring that does not bear the aldimine functionality is further functionalized with at least one of: aliphatic group, electron withdrawing group, electron donating group. Previously presented
The method of claim 82, wherein an altered aromatic aldimine is added to the reaction mixture to control the length of the polyquinolines, wherein the altered aromatic aldimine comprises all of the elements of the bifunctional aromatic aldimine except for one element chosen from the list: the aromatic terminal alkyne functionality or the aldimine functionality. Currently amended
A method of forming nitrogen-doped graphene nanoribbons comprising: reactin g a bifunctional aromatic aldimine with itself in the presence of a Lewis acid mediator and an oxidant to produce the correspondin g pol vq uinoline, and formin g intramolecular C-C bonds between aromatic and heteroaromatic moieties of the corresponding pol yq uinoline to form the corresponding nitro g en-doped graphene nanoribbon, wherein: the bifunctional aromatic aldimine is of formula: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.5.svg 1.35 1.07 Black and white comprising: an aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1, and the aromatic core is optionally substituted at any of its aromatic or heteroaromatic rings with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; an aldimine functionality immediately and covalentl y attached to the aromatic core, wherein R is an aromatic or heteroaromatic functionality optionally substituted with one or more substituents, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron donating functionality, or any combination thereof; and an aromatic terminal alkyne functionality immediatel y and covalent lv attached to the aromatic core; and wherein the aldimine functionality of one molecule of the bifunctional aromatic aldimine reacts with the aromatic terminal alkyne functionality of another molecule of the bifunctional aromatic aldimine to yield the polyquinolines comprising quinoline moieties incorporating the nitrogens of the aldimine functionalities:. Currently amended
The method of claim 90, wherein the intramolecular C-C bonds are formed via cyclodehydrogenation. Currently amended
The method of claim 90, wherein n is 2 such that the aromatic core is a naphthyl and the q uinoline moieties are benzoquinoline. Currently amended
The method of claim 90, wherein the corresponding nitrogen- doped graphene nanoribbon is a nitrogen-doped N=7 armchair graphene nanoribbon. Currently amended
The method of claim 90, wherein the correspondin q polv q uinoline is a polyquinoline with a plurality of quinolines interlinked at the 4 and 6 positions. Currently amended
A method of producing nitro g en-doped g raphene seq ments comprising: reactin q an aromatic aldimine with an aromatic bialk yny l in the presence of a Lewis acid mediator and an oxidant to produce the correspondin g bi q uinoline; and formin g intramolecular C-C bonds between aromatic and heteroaromatic moieties of the correspondin q bi q uinoline to form the correspondin q nitro q en-doped g raphene seg ment, wherein: the aromatic aldimine is of formula: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.6.svg 1 0.96 Black and white comprising: a first aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1 s and the first aromatic core is optionally substituted at any of its aromatic or heteroaromatic rings with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; and an aldimine functionality attached to the first aromatic core, wherein R is an aromatic or heteroaromatic functionality optionally substituted with one or more substituents, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.7.svg 0.16 4 Black and white the aromatic bi alkynyl, comprises a second aromatic core and two aromatic terminal alkyne functionalities; and SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.8.svg 0.12 0.58 Black and white the aldimine functionalities of two molecules of the aromatic aldimine react[[s]] with the two aromatic terminal alkyne functionalities of one molecule of the aromatic bi alkynyl to yield quinoline moieties incorporating the nitrogens of the aldimine functionalities. Currently amended
The method of claim 98, wherein n is 2 such that the first aromatic core is a naphthyl, and the q uinoline moieties are benzoquinoline. Currently amended
The method of claim 98, wherein n is 2 and the ring of the first aromatic core that does not bear the aldimine functionality is heteroaromatic. Previously presented
The method of claim 98, wherein n is at least 2 and some or all of the aromatic rings of the first aromatic core are linked at the 4 and 6 positions rather than fused, such that the aromaticity of the aromatic core is maintained. Previously presented
The method of claim 98, wherein the second aromatic core is a naphthyl moiety. Previously presented
The method of claim 98, wherein n is 1, the aromatic alkynyl is 1,5-dichloro-9, 1 0-diethynylanthracene, and two intramolecular C-C bonds are formed via Heck reaction such that the correspondin q nitro g en-doped raphene se q ment i s a rubicene nitrogen-doped molecular segment. Currently amended
The method of claim 98, wherein n is 1, the aromatic alkynyl is 1,5-dichloro-9, 1 0-diethynylanthracene, and two intramolecular C-C bonds are formed via base mediated cyclodehydrogenation reaction such that the correspondin g nitro g en-doped graphene se g ment is a tetrabenzopentacene nitrogen-doped molecular segment. Currently amended
Materials described outside the worked examples.
bifunctional aromatic aldimine
aromatic mono- or bialkynyl
bi-quinoline or polyquinoline
Additional fabrication and treatment steps described in the patent.
Patent
Atlas literature
Patent
US 10,899,711Patent drawings and their descriptions. Click a drawing to enlarge it.
FIG. 2B). In still yet other embodiments n is at least 2 such that a polybenzoquinline polybenzo q uinoline product may be formed. In some such embodiments the …
FIG. 3A, these species are merely exemplary. It will be understood that the synthesis scheme may be generalized by altering the nature of the aromatic …
FIG. 4B. In addition, although the R-group in the exemplary embodiment provided in
FIGS. 6 and 7, it should be understood that the R-group in accordance with embodiments may further comprise one or more par a-or meta- substituted …
FIGS. 8A, 8B and 9A, compounds 3b, 5b, 8 and 11 a) may be adapted to furnish substituted polybenzoquinolines (e.g.,
FIG. 9A) is slightly modified. In such embodiments the bifunctional monomer comprising the requisite alkyne and aldimine functional groups incorporates an …
FIGS. 18A to 18 D. As demonstrated, the modular nature of such functionalities allows for a wide- variety of substitution, including, for example, aromatic rin …
Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
1-48. Canceled
Canceled
A method of producing bi-quinolines or polyquinolines comprising: reactin q a bifunctional aromatic aldimine with an aromatic mono- or bialk vnv l in the presence of a Lewis acid mediator and an oxidant to produce the corresponding bi- q uinoline or pol yc uinoline, wherein: the bifunctional aromatic aldimine is of formula: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.1.svg 1.26 1.26 Black and white comprising: a first aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1. and the first aromatic core is optionally substituted with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; a first aldimine functionality immediately and covalentl y attached to the first aromatic core, wherein R₁ is an aromatic or heteroaromatic functionality optionally substituted with one or more substituents, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron donating functionality, or any combination thereof; and a second aldimine functionality immediatel y and covalent lv attached to the first aromatic core, wherein R₂ is one of the functionalities selected from the g roup of: R1, a substituted aromatic rin g, an [[or]] unsubstituted aromatic ring, a [[or]] substituted heteroaromatic ring, and an unsubstituted heteroaromatic rin g; and the aromatic mono- or bi alkynyl comprises a second aromatic core and one or two aromatic terminal alkyne functionalities respectivel y; and wherein the first and the second aldimine functionalities of the bifunctional aromatic aldimine react with the one or two aromatic terminal alkyne functionalities of the aromatic mono- or bi alkynyl to yield the corresponding bi-quinoline or polyquinoline[[s]] comprising quinoline moieties incorporating the nitrogens of the first and the second aldimine functionalities. Currently amended
The method of claim 49, wherein n is 2 such that the first aromatic core is a naphthyl and the q uinoline moieties are benzoquinoline. Currently amended
The method of claim 49, wherein n is 2 and the ring that does not bear the first aldimine functionality is heteroaromatic. Previously presented
The method of claim 49, wherein n is at least 2 and some or all of the aromatic rings of the first aromatic core are linked at the 4 and 6 positions rather than fused, such that the aromaticity of the first aromatic core is maintained. Previously presented
The method of claim 49, wherein the second aromatic core is a naphthyl moiety. Previously presented
The method of claim 49, wherein both the aromatic mono alkynyl comprising one aromatic terminal alkyne functionality and the aromatic bialkynyl comprising two aromatic alkyne functionalities are used in the same reaction mixture to control the length of the polyquinolines. Currently amended
50-52. Canceled
Canceled
Canceled
A method of forming nitrogen-doped aromatic molecular segments or graphene nanoribbons comprising: reactin g a bifunctional aromatic aldimine with an aromatic mono- or bialk yny l in the presence of a Lewis acid mediator and an oxidant to produce the correspondin g bi- q uinoline or pol vc uinoline, and formin g intramolecular C-C bonds between aromatic and heteroaromatic moieties of the correspondin g bi- q uinoline or po lyq uino l ine to form the correspondin g nitrogen- doped molecular se g ment or g raphene nanoribbon, wherein: the bifunctional aromatic aldimine is of formula: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.2.svg 1.26 1.26 Black and white comprising: a first aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1 s and the first aromatic core is optionally substituted at any of its aromatic or heteroaromatic rings with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; a first aldimine functionality immediately and covalentl y attached to the first aromatic core, wherein R₁ is an aromatic or heteroaromatic functionality optionally substituted with one or more substituents, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron donating functionality, or any combination thereof; and a second aldimine functionality immediately and covalentl y attached to the first aromatic core, wherein R₂ is one of the functionalities selected from the g roup of: R1, a substituted aromatic rin g, an [[or]] unsubstituted aromatic ring, a [[or]] substituted heteroaromatic ring, and an unsubstituted heteroaromatic rin g; and the aromatic mono- or bi alkynyl comprises a second aromatic core, and one or two aromatic terminal alkyne functionalities, respectivel y; and wherein the first and the second aldimine functionalities of the bifunctional aromatic aldimine react with the one or two aromatic terminal alkyne functionalities of the aromatic mono- or bi alkynyl to yield the corresponding bi-quinoline or polyquinoline[[s]] comprising quinoline moieties incorporating the nitrogens of the first and the second aldimine functionalities. Currently amended
The method of claim 62, wherein n is 1, the first aromatic core is a benzene additionally substituted with two C l functionalities at positions 2 and 5, the second aldimine functionality is located at position 4, the aromatic mono alkynyl is phenylacetylene, and two intramolecular C-C bonds are formed via Heck reaction fe such that the correspondin g nitro g en-doped molecular se g ment or g raphene nanoribbon is a rubicene nitrogen-doped molecular segment. Currently amended
The method of claim 62, wherein n is 1, the first aromatic core is a benzene additionally substituted with two C l functionalities at positions 2 and 5, the second aldimine functionality is located at position 4, the aromatic mono alkynyl is naphthyl alkyne, and two intramolecular C-C bonds are formed via base mediated cyclodehydrogenation reaction such that the correspondin g nitro g en-doped molecular se g ment or g raphene nanoribbon is a tetrabenzopentacene nitrogen-doped molecular segment. Currently amended
The method of claim 62, wherein the aromatic i alkynyl is 1,5-dichloro-9,1 0-diethynylanthracene, and intramolecular C-C bonds are formed via Heck reaction. Currently amended
The method of claim 62, wherein the aromatic i alkynyl is 1,5-dichloro-9,1 0-diethynylanthracene, and intramolecular C-C bonds are formed via base mediated cyclodehydrogenation reaction. Currently amended
67-74. Canceled
Canceled
A[[n]] bifunctional aromatic aldimine for producing quinolines, polyquinolines, nitrogen-doped aromatic molecular segments, and graphene nanoribbons according to: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.3.svg 1.4 1.33 Black and white and comprising: an aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1 s and the aromatic core is optionally substituted at any of its aromatic or heteroaromatic rings with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; an aldimine functionality immediately and covalently attached to the aromatic core, wherein R is a substituted or unsubstituted aromatic or heteroaromatic ring; and an aromatic terminal alkyne functionality immediately and covalently attached at any position of the aromatic core and capable of reacting with an aromatic aldimine in an aza-Diels Alder Povarov reaction. Currently amended
(Curren l ty Amended) The bifunctional aromatic aldimine of claim 75, wherein R is substituted with at least one functionality, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron donating functionality, or any combination thereof. Currently amended
The bifunctional aromatic aldimine of claim 75, wherein n is at least 2. Currently amended
The bifunctional aromatic aldimine of claim 75, wherein n is 2 and the ring that does not bear the aldimine functionality is heteroaromatic. Currently amended
The bifunctional aromatic aldimine of claim 75, wherein n is 2 and the ring that does not bear the aldimine functionality is further functionalized with at least one of: aliphatic group, electron withdrawing group, electron donating group. Currently amended
The bifunctional aromatic aldimine of claim 75, wherein n is at least 2 and some or all of the aromatic rings of the aromatic core are linked at the 4 and 6 positions rather than fused, such that the aromaticity of the aromatic core is maintained. Currently amended
A method of producing polyquinolines comprising: reactin g a bifunctional aromatic aldimine with itself in the presence of a Lewis acid mediator and an oxidant to produce the correspondin g po lyc uino l ine, wherein: the bifunctional aromatic aldimine is of formula: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.4.svg 1.35 1.07 Black and white comprising: an aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1, and the aromatic core is optionally substituted at any of its aromatic or heteroaromatic rings with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; an aldimine functionality immediately and covalentl y attached to the aromatic core, wherein R is an aromatic or heteroaromatic functionality optionally substituted with one or more substituents, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron donating functionality, or any combination thereof; and an aromatic terminal alkyne functionality immediately and covalentl y attached at any position of the aromatic core; and wherein the aldimine functionality of one molecule of the bifunctional aromatic aldimine reacts with the aromatic terminal alkyne functionality of another molecule of the bifunctional aromatic aldimine to yield the correspondin g polyquinoline[[s]] comprising quinoline moieties incorporating the nitrogens of the aldimine functionalities. Currently amended
The method of claim 82, wherein n is 2 such that the aromatic core is a naphthyl and the q uinoline moieties are benzoquinoline. Currently amended
The method of claim 82, wherein n is 2 and the ring that does not bear the aldimine functionality is heteroaromatic. Previously presented
The method of claim 82, wherein n is at least 2 and some or all of the aromatic rings of the aromatic core are linked at the 4 and 6 positions rather than fused, such that the aromaticity of the aromatic core is maintained. Previously presented
The method of claim 82, wherein n is at least 2 and any ring that does not bear the aldimine functionality is further functionalized with at least one of: aliphatic group, electron withdrawing group, electron donating group. Previously presented
The method of claim 82, wherein an altered aromatic aldimine is added to the reaction mixture to control the length of the polyquinolines, wherein the altered aromatic aldimine comprises all of the elements of the bifunctional aromatic aldimine except for one element chosen from the list: the aromatic terminal alkyne functionality or the aldimine functionality. Currently amended
A method of forming nitrogen-doped graphene nanoribbons comprising: reactin g a bifunctional aromatic aldimine with itself in the presence of a Lewis acid mediator and an oxidant to produce the correspondin g pol vq uinoline, and formin g intramolecular C-C bonds between aromatic and heteroaromatic moieties of the corresponding pol yq uinoline to form the corresponding nitro g en-doped graphene nanoribbon, wherein: the bifunctional aromatic aldimine is of formula: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.5.svg 1.35 1.07 Black and white comprising: an aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1, and the aromatic core is optionally substituted at any of its aromatic or heteroaromatic rings with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; an aldimine functionality immediately and covalentl y attached to the aromatic core, wherein R is an aromatic or heteroaromatic functionality optionally substituted with one or more substituents, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron donating functionality, or any combination thereof; and an aromatic terminal alkyne functionality immediatel y and covalent lv attached to the aromatic core; and wherein the aldimine functionality of one molecule of the bifunctional aromatic aldimine reacts with the aromatic terminal alkyne functionality of another molecule of the bifunctional aromatic aldimine to yield the polyquinolines comprising quinoline moieties incorporating the nitrogens of the aldimine functionalities:. Currently amended
The method of claim 90, wherein the intramolecular C-C bonds are formed via cyclodehydrogenation. Currently amended
The method of claim 90, wherein n is 2 such that the aromatic core is a naphthyl and the q uinoline moieties are benzoquinoline. Currently amended
The method of claim 90, wherein the corresponding nitrogen- doped graphene nanoribbon is a nitrogen-doped N=7 armchair graphene nanoribbon. Currently amended
The method of claim 90, wherein the correspondin q polv q uinoline is a polyquinoline with a plurality of quinolines interlinked at the 4 and 6 positions. Currently amended
A method of producing nitro g en-doped g raphene seq ments comprising: reactin q an aromatic aldimine with an aromatic bialk yny l in the presence of a Lewis acid mediator and an oxidant to produce the correspondin g bi q uinoline; and formin g intramolecular C-C bonds between aromatic and heteroaromatic moieties of the correspondin q bi q uinoline to form the correspondin q nitro q en-doped g raphene seg ment, wherein: the aromatic aldimine is of formula: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.6.svg 1 0.96 Black and white comprising: a first aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1 s and the first aromatic core is optionally substituted at any of its aromatic or heteroaromatic rings with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; and an aldimine functionality attached to the first aromatic core, wherein R is an aromatic or heteroaromatic functionality optionally substituted with one or more substituents, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.7.svg 0.16 4 Black and white the aromatic bi alkynyl, comprises a second aromatic core and two aromatic terminal alkyne functionalities; and SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.8.svg 0.12 0.58 Black and white the aldimine functionalities of two molecules of the aromatic aldimine react[[s]] with the two aromatic terminal alkyne functionalities of one molecule of the aromatic bi alkynyl to yield quinoline moieties incorporating the nitrogens of the aldimine functionalities. Currently amended
The method of claim 98, wherein n is 2 such that the first aromatic core is a naphthyl, and the q uinoline moieties are benzoquinoline. Currently amended
The method of claim 98, wherein n is 2 and the ring of the first aromatic core that does not bear the aldimine functionality is heteroaromatic. Previously presented
The method of claim 98, wherein n is at least 2 and some or all of the aromatic rings of the first aromatic core are linked at the 4 and 6 positions rather than fused, such that the aromaticity of the aromatic core is maintained. Previously presented
The method of claim 98, wherein the second aromatic core is a naphthyl moiety. Previously presented
The method of claim 98, wherein n is 1, the aromatic alkynyl is 1,5-dichloro-9, 1 0-diethynylanthracene, and two intramolecular C-C bonds are formed via Heck reaction such that the correspondin q nitro g en-doped raphene se q ment i s a rubicene nitrogen-doped molecular segment. Currently amended
The method of claim 98, wherein n is 1, the aromatic alkynyl is 1,5-dichloro-9, 1 0-diethynylanthracene, and two intramolecular C-C bonds are formed via base mediated cyclodehydrogenation reaction such that the correspondin g nitro g en-doped graphene se g ment is a tetrabenzopentacene nitrogen-doped molecular segment. Currently amended
Materials described outside the worked examples.
bifunctional aromatic aldimine
aromatic mono- or bialkynyl
bi-quinoline or polyquinoline
Additional fabrication and treatment steps described in the patent.
Patent
Atlas literature
Patent
US 10,899,711Patent drawings and their descriptions. Click a drawing to enlarge it.
FIG. 2B). In still yet other embodiments n is at least 2 such that a polybenzoquinline polybenzo q uinoline product may be formed. In some such embodiments the …
FIG. 3A, these species are merely exemplary. It will be understood that the synthesis scheme may be generalized by altering the nature of the aromatic …
FIG. 4B. In addition, although the R-group in the exemplary embodiment provided in
FIGS. 6 and 7, it should be understood that the R-group in accordance with embodiments may further comprise one or more par a-or meta- substituted …
FIGS. 8A, 8B and 9A, compounds 3b, 5b, 8 and 11 a) may be adapted to furnish substituted polybenzoquinolines (e.g.,
FIG. 9A) is slightly modified. In such embodiments the bifunctional monomer comprising the requisite alkyne and aldimine functional groups incorporates an …
FIGS. 18A to 18 D. As demonstrated, the modular nature of such functionalities allows for a wide- variety of substitution, including, for example, aromatic rin …
Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
1-48. Canceled
Canceled
A method of producing bi-quinolines or polyquinolines comprising: reactin q a bifunctional aromatic aldimine with an aromatic mono- or bialk vnv l in the presence of a Lewis acid mediator and an oxidant to produce the corresponding bi- q uinoline or pol yc uinoline, wherein: the bifunctional aromatic aldimine is of formula: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.1.svg 1.26 1.26 Black and white comprising: a first aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1. and the first aromatic core is optionally substituted with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; a first aldimine functionality immediately and covalentl y attached to the first aromatic core, wherein R₁ is an aromatic or heteroaromatic functionality optionally substituted with one or more substituents, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron donating functionality, or any combination thereof; and a second aldimine functionality immediatel y and covalent lv attached to the first aromatic core, wherein R₂ is one of the functionalities selected from the g roup of: R1, a substituted aromatic rin g, an [[or]] unsubstituted aromatic ring, a [[or]] substituted heteroaromatic ring, and an unsubstituted heteroaromatic rin g; and the aromatic mono- or bi alkynyl comprises a second aromatic core and one or two aromatic terminal alkyne functionalities respectivel y; and wherein the first and the second aldimine functionalities of the bifunctional aromatic aldimine react with the one or two aromatic terminal alkyne functionalities of the aromatic mono- or bi alkynyl to yield the corresponding bi-quinoline or polyquinoline[[s]] comprising quinoline moieties incorporating the nitrogens of the first and the second aldimine functionalities. Currently amended
The method of claim 49, wherein n is 2 such that the first aromatic core is a naphthyl and the q uinoline moieties are benzoquinoline. Currently amended
The method of claim 49, wherein n is 2 and the ring that does not bear the first aldimine functionality is heteroaromatic. Previously presented
The method of claim 49, wherein n is at least 2 and some or all of the aromatic rings of the first aromatic core are linked at the 4 and 6 positions rather than fused, such that the aromaticity of the first aromatic core is maintained. Previously presented
The method of claim 49, wherein the second aromatic core is a naphthyl moiety. Previously presented
The method of claim 49, wherein both the aromatic mono alkynyl comprising one aromatic terminal alkyne functionality and the aromatic bialkynyl comprising two aromatic alkyne functionalities are used in the same reaction mixture to control the length of the polyquinolines. Currently amended
50-52. Canceled
Canceled
Canceled
A method of forming nitrogen-doped aromatic molecular segments or graphene nanoribbons comprising: reactin g a bifunctional aromatic aldimine with an aromatic mono- or bialk yny l in the presence of a Lewis acid mediator and an oxidant to produce the correspondin g bi- q uinoline or pol vc uinoline, and formin g intramolecular C-C bonds between aromatic and heteroaromatic moieties of the correspondin g bi- q uinoline or po lyq uino l ine to form the correspondin g nitrogen- doped molecular se g ment or g raphene nanoribbon, wherein: the bifunctional aromatic aldimine is of formula: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.2.svg 1.26 1.26 Black and white comprising: a first aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1 s and the first aromatic core is optionally substituted at any of its aromatic or heteroaromatic rings with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; a first aldimine functionality immediately and covalentl y attached to the first aromatic core, wherein R₁ is an aromatic or heteroaromatic functionality optionally substituted with one or more substituents, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron donating functionality, or any combination thereof; and a second aldimine functionality immediately and covalentl y attached to the first aromatic core, wherein R₂ is one of the functionalities selected from the g roup of: R1, a substituted aromatic rin g, an [[or]] unsubstituted aromatic ring, a [[or]] substituted heteroaromatic ring, and an unsubstituted heteroaromatic rin g; and the aromatic mono- or bi alkynyl comprises a second aromatic core, and one or two aromatic terminal alkyne functionalities, respectivel y; and wherein the first and the second aldimine functionalities of the bifunctional aromatic aldimine react with the one or two aromatic terminal alkyne functionalities of the aromatic mono- or bi alkynyl to yield the corresponding bi-quinoline or polyquinoline[[s]] comprising quinoline moieties incorporating the nitrogens of the first and the second aldimine functionalities. Currently amended
The method of claim 62, wherein n is 1, the first aromatic core is a benzene additionally substituted with two C l functionalities at positions 2 and 5, the second aldimine functionality is located at position 4, the aromatic mono alkynyl is phenylacetylene, and two intramolecular C-C bonds are formed via Heck reaction fe such that the correspondin g nitro g en-doped molecular se g ment or g raphene nanoribbon is a rubicene nitrogen-doped molecular segment. Currently amended
The method of claim 62, wherein n is 1, the first aromatic core is a benzene additionally substituted with two C l functionalities at positions 2 and 5, the second aldimine functionality is located at position 4, the aromatic mono alkynyl is naphthyl alkyne, and two intramolecular C-C bonds are formed via base mediated cyclodehydrogenation reaction such that the correspondin g nitro g en-doped molecular se g ment or g raphene nanoribbon is a tetrabenzopentacene nitrogen-doped molecular segment. Currently amended
The method of claim 62, wherein the aromatic i alkynyl is 1,5-dichloro-9,1 0-diethynylanthracene, and intramolecular C-C bonds are formed via Heck reaction. Currently amended
The method of claim 62, wherein the aromatic i alkynyl is 1,5-dichloro-9,1 0-diethynylanthracene, and intramolecular C-C bonds are formed via base mediated cyclodehydrogenation reaction. Currently amended
67-74. Canceled
Canceled
A[[n]] bifunctional aromatic aldimine for producing quinolines, polyquinolines, nitrogen-doped aromatic molecular segments, and graphene nanoribbons according to: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.3.svg 1.4 1.33 Black and white and comprising: an aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1 s and the aromatic core is optionally substituted at any of its aromatic or heteroaromatic rings with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; an aldimine functionality immediately and covalently attached to the aromatic core, wherein R is a substituted or unsubstituted aromatic or heteroaromatic ring; and an aromatic terminal alkyne functionality immediately and covalently attached at any position of the aromatic core and capable of reacting with an aromatic aldimine in an aza-Diels Alder Povarov reaction. Currently amended
(Curren l ty Amended) The bifunctional aromatic aldimine of claim 75, wherein R is substituted with at least one functionality, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron donating functionality, or any combination thereof. Currently amended
The bifunctional aromatic aldimine of claim 75, wherein n is at least 2. Currently amended
The bifunctional aromatic aldimine of claim 75, wherein n is 2 and the ring that does not bear the aldimine functionality is heteroaromatic. Currently amended
The bifunctional aromatic aldimine of claim 75, wherein n is 2 and the ring that does not bear the aldimine functionality is further functionalized with at least one of: aliphatic group, electron withdrawing group, electron donating group. Currently amended
The bifunctional aromatic aldimine of claim 75, wherein n is at least 2 and some or all of the aromatic rings of the aromatic core are linked at the 4 and 6 positions rather than fused, such that the aromaticity of the aromatic core is maintained. Currently amended
A method of producing polyquinolines comprising: reactin g a bifunctional aromatic aldimine with itself in the presence of a Lewis acid mediator and an oxidant to produce the correspondin g po lyc uino l ine, wherein: the bifunctional aromatic aldimine is of formula: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.4.svg 1.35 1.07 Black and white comprising: an aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1, and the aromatic core is optionally substituted at any of its aromatic or heteroaromatic rings with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; an aldimine functionality immediately and covalentl y attached to the aromatic core, wherein R is an aromatic or heteroaromatic functionality optionally substituted with one or more substituents, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron donating functionality, or any combination thereof; and an aromatic terminal alkyne functionality immediately and covalentl y attached at any position of the aromatic core; and wherein the aldimine functionality of one molecule of the bifunctional aromatic aldimine reacts with the aromatic terminal alkyne functionality of another molecule of the bifunctional aromatic aldimine to yield the correspondin g polyquinoline[[s]] comprising quinoline moieties incorporating the nitrogens of the aldimine functionalities. Currently amended
The method of claim 82, wherein n is 2 such that the aromatic core is a naphthyl and the q uinoline moieties are benzoquinoline. Currently amended
The method of claim 82, wherein n is 2 and the ring that does not bear the aldimine functionality is heteroaromatic. Previously presented
The method of claim 82, wherein n is at least 2 and some or all of the aromatic rings of the aromatic core are linked at the 4 and 6 positions rather than fused, such that the aromaticity of the aromatic core is maintained. Previously presented
The method of claim 82, wherein n is at least 2 and any ring that does not bear the aldimine functionality is further functionalized with at least one of: aliphatic group, electron withdrawing group, electron donating group. Previously presented
The method of claim 82, wherein an altered aromatic aldimine is added to the reaction mixture to control the length of the polyquinolines, wherein the altered aromatic aldimine comprises all of the elements of the bifunctional aromatic aldimine except for one element chosen from the list: the aromatic terminal alkyne functionality or the aldimine functionality. Currently amended
A method of forming nitrogen-doped graphene nanoribbons comprising: reactin g a bifunctional aromatic aldimine with itself in the presence of a Lewis acid mediator and an oxidant to produce the correspondin g pol vq uinoline, and formin g intramolecular C-C bonds between aromatic and heteroaromatic moieties of the corresponding pol yq uinoline to form the corresponding nitro g en-doped graphene nanoribbon, wherein: the bifunctional aromatic aldimine is of formula: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.5.svg 1.35 1.07 Black and white comprising: an aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1, and the aromatic core is optionally substituted at any of its aromatic or heteroaromatic rings with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; an aldimine functionality immediately and covalentl y attached to the aromatic core, wherein R is an aromatic or heteroaromatic functionality optionally substituted with one or more substituents, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron donating functionality, or any combination thereof; and an aromatic terminal alkyne functionality immediatel y and covalent lv attached to the aromatic core; and wherein the aldimine functionality of one molecule of the bifunctional aromatic aldimine reacts with the aromatic terminal alkyne functionality of another molecule of the bifunctional aromatic aldimine to yield the polyquinolines comprising quinoline moieties incorporating the nitrogens of the aldimine functionalities:. Currently amended
The method of claim 90, wherein the intramolecular C-C bonds are formed via cyclodehydrogenation. Currently amended
The method of claim 90, wherein n is 2 such that the aromatic core is a naphthyl and the q uinoline moieties are benzoquinoline. Currently amended
The method of claim 90, wherein the corresponding nitrogen- doped graphene nanoribbon is a nitrogen-doped N=7 armchair graphene nanoribbon. Currently amended
The method of claim 90, wherein the correspondin q polv q uinoline is a polyquinoline with a plurality of quinolines interlinked at the 4 and 6 positions. Currently amended
A method of producing nitro g en-doped g raphene seq ments comprising: reactin q an aromatic aldimine with an aromatic bialk yny l in the presence of a Lewis acid mediator and an oxidant to produce the correspondin g bi q uinoline; and formin g intramolecular C-C bonds between aromatic and heteroaromatic moieties of the correspondin q bi q uinoline to form the correspondin q nitro q en-doped g raphene seg ment, wherein: the aromatic aldimine is of formula: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.6.svg 1 0.96 Black and white comprising: a first aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1 s and the first aromatic core is optionally substituted at any of its aromatic or heteroaromatic rings with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; and an aldimine functionality attached to the first aromatic core, wherein R is an aromatic or heteroaromatic functionality optionally substituted with one or more substituents, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.7.svg 0.16 4 Black and white the aromatic bi alkynyl, comprises a second aromatic core and two aromatic terminal alkyne functionalities; and SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.8.svg 0.12 0.58 Black and white the aldimine functionalities of two molecules of the aromatic aldimine react[[s]] with the two aromatic terminal alkyne functionalities of one molecule of the aromatic bi alkynyl to yield quinoline moieties incorporating the nitrogens of the aldimine functionalities. Currently amended
The method of claim 98, wherein n is 2 such that the first aromatic core is a naphthyl, and the q uinoline moieties are benzoquinoline. Currently amended
The method of claim 98, wherein n is 2 and the ring of the first aromatic core that does not bear the aldimine functionality is heteroaromatic. Previously presented
The method of claim 98, wherein n is at least 2 and some or all of the aromatic rings of the first aromatic core are linked at the 4 and 6 positions rather than fused, such that the aromaticity of the aromatic core is maintained. Previously presented
The method of claim 98, wherein the second aromatic core is a naphthyl moiety. Previously presented
The method of claim 98, wherein n is 1, the aromatic alkynyl is 1,5-dichloro-9, 1 0-diethynylanthracene, and two intramolecular C-C bonds are formed via Heck reaction such that the correspondin q nitro g en-doped raphene se q ment i s a rubicene nitrogen-doped molecular segment. Currently amended
The method of claim 98, wherein n is 1, the aromatic alkynyl is 1,5-dichloro-9, 1 0-diethynylanthracene, and two intramolecular C-C bonds are formed via base mediated cyclodehydrogenation reaction such that the correspondin g nitro g en-doped graphene se g ment is a tetrabenzopentacene nitrogen-doped molecular segment. Currently amended
Materials described outside the worked examples.
bifunctional aromatic aldimine
aromatic mono- or bialkynyl
bi-quinoline or polyquinoline
Additional fabrication and treatment steps described in the patent.
Patent
Atlas literature
Patent
US 10,899,711Patent drawings and their descriptions. Click a drawing to enlarge it.
FIG. 2B). In still yet other embodiments n is at least 2 such that a polybenzoquinline polybenzo q uinoline product may be formed. In some such embodiments the …
FIG. 3A, these species are merely exemplary. It will be understood that the synthesis scheme may be generalized by altering the nature of the aromatic …
FIG. 4B. In addition, although the R-group in the exemplary embodiment provided in
FIGS. 6 and 7, it should be understood that the R-group in accordance with embodiments may further comprise one or more par a-or meta- substituted …
FIGS. 8A, 8B and 9A, compounds 3b, 5b, 8 and 11 a) may be adapted to furnish substituted polybenzoquinolines (e.g.,
FIG. 9A) is slightly modified. In such embodiments the bifunctional monomer comprising the requisite alkyne and aldimine functional groups incorporates an …
FIGS. 18A to 18 D. As demonstrated, the modular nature of such functionalities allows for a wide- variety of substitution, including, for example, aromatic rin …
Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
1-48. Canceled
Canceled
A method of producing bi-quinolines or polyquinolines comprising: reactin q a bifunctional aromatic aldimine with an aromatic mono- or bialk vnv l in the presence of a Lewis acid mediator and an oxidant to produce the corresponding bi- q uinoline or pol yc uinoline, wherein: the bifunctional aromatic aldimine is of formula: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.1.svg 1.26 1.26 Black and white comprising: a first aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1. and the first aromatic core is optionally substituted with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; a first aldimine functionality immediately and covalentl y attached to the first aromatic core, wherein R₁ is an aromatic or heteroaromatic functionality optionally substituted with one or more substituents, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron donating functionality, or any combination thereof; and a second aldimine functionality immediatel y and covalent lv attached to the first aromatic core, wherein R₂ is one of the functionalities selected from the g roup of: R1, a substituted aromatic rin g, an [[or]] unsubstituted aromatic ring, a [[or]] substituted heteroaromatic ring, and an unsubstituted heteroaromatic rin g; and the aromatic mono- or bi alkynyl comprises a second aromatic core and one or two aromatic terminal alkyne functionalities respectivel y; and wherein the first and the second aldimine functionalities of the bifunctional aromatic aldimine react with the one or two aromatic terminal alkyne functionalities of the aromatic mono- or bi alkynyl to yield the corresponding bi-quinoline or polyquinoline[[s]] comprising quinoline moieties incorporating the nitrogens of the first and the second aldimine functionalities. Currently amended
The method of claim 49, wherein n is 2 such that the first aromatic core is a naphthyl and the q uinoline moieties are benzoquinoline. Currently amended
The method of claim 49, wherein n is 2 and the ring that does not bear the first aldimine functionality is heteroaromatic. Previously presented
The method of claim 49, wherein n is at least 2 and some or all of the aromatic rings of the first aromatic core are linked at the 4 and 6 positions rather than fused, such that the aromaticity of the first aromatic core is maintained. Previously presented
The method of claim 49, wherein the second aromatic core is a naphthyl moiety. Previously presented
The method of claim 49, wherein both the aromatic mono alkynyl comprising one aromatic terminal alkyne functionality and the aromatic bialkynyl comprising two aromatic alkyne functionalities are used in the same reaction mixture to control the length of the polyquinolines. Currently amended
50-52. Canceled
Canceled
Canceled
A method of forming nitrogen-doped aromatic molecular segments or graphene nanoribbons comprising: reactin g a bifunctional aromatic aldimine with an aromatic mono- or bialk yny l in the presence of a Lewis acid mediator and an oxidant to produce the correspondin g bi- q uinoline or pol vc uinoline, and formin g intramolecular C-C bonds between aromatic and heteroaromatic moieties of the correspondin g bi- q uinoline or po lyq uino l ine to form the correspondin g nitrogen- doped molecular se g ment or g raphene nanoribbon, wherein: the bifunctional aromatic aldimine is of formula: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.2.svg 1.26 1.26 Black and white comprising: a first aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1 s and the first aromatic core is optionally substituted at any of its aromatic or heteroaromatic rings with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; a first aldimine functionality immediately and covalentl y attached to the first aromatic core, wherein R₁ is an aromatic or heteroaromatic functionality optionally substituted with one or more substituents, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron donating functionality, or any combination thereof; and a second aldimine functionality immediately and covalentl y attached to the first aromatic core, wherein R₂ is one of the functionalities selected from the g roup of: R1, a substituted aromatic rin g, an [[or]] unsubstituted aromatic ring, a [[or]] substituted heteroaromatic ring, and an unsubstituted heteroaromatic rin g; and the aromatic mono- or bi alkynyl comprises a second aromatic core, and one or two aromatic terminal alkyne functionalities, respectivel y; and wherein the first and the second aldimine functionalities of the bifunctional aromatic aldimine react with the one or two aromatic terminal alkyne functionalities of the aromatic mono- or bi alkynyl to yield the corresponding bi-quinoline or polyquinoline[[s]] comprising quinoline moieties incorporating the nitrogens of the first and the second aldimine functionalities. Currently amended
The method of claim 62, wherein n is 1, the first aromatic core is a benzene additionally substituted with two C l functionalities at positions 2 and 5, the second aldimine functionality is located at position 4, the aromatic mono alkynyl is phenylacetylene, and two intramolecular C-C bonds are formed via Heck reaction fe such that the correspondin g nitro g en-doped molecular se g ment or g raphene nanoribbon is a rubicene nitrogen-doped molecular segment. Currently amended
The method of claim 62, wherein n is 1, the first aromatic core is a benzene additionally substituted with two C l functionalities at positions 2 and 5, the second aldimine functionality is located at position 4, the aromatic mono alkynyl is naphthyl alkyne, and two intramolecular C-C bonds are formed via base mediated cyclodehydrogenation reaction such that the correspondin g nitro g en-doped molecular se g ment or g raphene nanoribbon is a tetrabenzopentacene nitrogen-doped molecular segment. Currently amended
The method of claim 62, wherein the aromatic i alkynyl is 1,5-dichloro-9,1 0-diethynylanthracene, and intramolecular C-C bonds are formed via Heck reaction. Currently amended
The method of claim 62, wherein the aromatic i alkynyl is 1,5-dichloro-9,1 0-diethynylanthracene, and intramolecular C-C bonds are formed via base mediated cyclodehydrogenation reaction. Currently amended
67-74. Canceled
Canceled
A[[n]] bifunctional aromatic aldimine for producing quinolines, polyquinolines, nitrogen-doped aromatic molecular segments, and graphene nanoribbons according to: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.3.svg 1.4 1.33 Black and white and comprising: an aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1 s and the aromatic core is optionally substituted at any of its aromatic or heteroaromatic rings with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; an aldimine functionality immediately and covalently attached to the aromatic core, wherein R is a substituted or unsubstituted aromatic or heteroaromatic ring; and an aromatic terminal alkyne functionality immediately and covalently attached at any position of the aromatic core and capable of reacting with an aromatic aldimine in an aza-Diels Alder Povarov reaction. Currently amended
(Curren l ty Amended) The bifunctional aromatic aldimine of claim 75, wherein R is substituted with at least one functionality, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron donating functionality, or any combination thereof. Currently amended
The bifunctional aromatic aldimine of claim 75, wherein n is at least 2. Currently amended
The bifunctional aromatic aldimine of claim 75, wherein n is 2 and the ring that does not bear the aldimine functionality is heteroaromatic. Currently amended
The bifunctional aromatic aldimine of claim 75, wherein n is 2 and the ring that does not bear the aldimine functionality is further functionalized with at least one of: aliphatic group, electron withdrawing group, electron donating group. Currently amended
The bifunctional aromatic aldimine of claim 75, wherein n is at least 2 and some or all of the aromatic rings of the aromatic core are linked at the 4 and 6 positions rather than fused, such that the aromaticity of the aromatic core is maintained. Currently amended
A method of producing polyquinolines comprising: reactin g a bifunctional aromatic aldimine with itself in the presence of a Lewis acid mediator and an oxidant to produce the correspondin g po lyc uino l ine, wherein: the bifunctional aromatic aldimine is of formula: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.4.svg 1.35 1.07 Black and white comprising: an aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1, and the aromatic core is optionally substituted at any of its aromatic or heteroaromatic rings with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; an aldimine functionality immediately and covalentl y attached to the aromatic core, wherein R is an aromatic or heteroaromatic functionality optionally substituted with one or more substituents, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron donating functionality, or any combination thereof; and an aromatic terminal alkyne functionality immediately and covalentl y attached at any position of the aromatic core; and wherein the aldimine functionality of one molecule of the bifunctional aromatic aldimine reacts with the aromatic terminal alkyne functionality of another molecule of the bifunctional aromatic aldimine to yield the correspondin g polyquinoline[[s]] comprising quinoline moieties incorporating the nitrogens of the aldimine functionalities. Currently amended
The method of claim 82, wherein n is 2 such that the aromatic core is a naphthyl and the q uinoline moieties are benzoquinoline. Currently amended
The method of claim 82, wherein n is 2 and the ring that does not bear the aldimine functionality is heteroaromatic. Previously presented
The method of claim 82, wherein n is at least 2 and some or all of the aromatic rings of the aromatic core are linked at the 4 and 6 positions rather than fused, such that the aromaticity of the aromatic core is maintained. Previously presented
The method of claim 82, wherein n is at least 2 and any ring that does not bear the aldimine functionality is further functionalized with at least one of: aliphatic group, electron withdrawing group, electron donating group. Previously presented
The method of claim 82, wherein an altered aromatic aldimine is added to the reaction mixture to control the length of the polyquinolines, wherein the altered aromatic aldimine comprises all of the elements of the bifunctional aromatic aldimine except for one element chosen from the list: the aromatic terminal alkyne functionality or the aldimine functionality. Currently amended
A method of forming nitrogen-doped graphene nanoribbons comprising: reactin g a bifunctional aromatic aldimine with itself in the presence of a Lewis acid mediator and an oxidant to produce the correspondin g pol vq uinoline, and formin g intramolecular C-C bonds between aromatic and heteroaromatic moieties of the corresponding pol yq uinoline to form the corresponding nitro g en-doped graphene nanoribbon, wherein: the bifunctional aromatic aldimine is of formula: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.5.svg 1.35 1.07 Black and white comprising: an aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1, and the aromatic core is optionally substituted at any of its aromatic or heteroaromatic rings with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; an aldimine functionality immediately and covalentl y attached to the aromatic core, wherein R is an aromatic or heteroaromatic functionality optionally substituted with one or more substituents, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron donating functionality, or any combination thereof; and an aromatic terminal alkyne functionality immediatel y and covalent lv attached to the aromatic core; and wherein the aldimine functionality of one molecule of the bifunctional aromatic aldimine reacts with the aromatic terminal alkyne functionality of another molecule of the bifunctional aromatic aldimine to yield the polyquinolines comprising quinoline moieties incorporating the nitrogens of the aldimine functionalities:. Currently amended
The method of claim 90, wherein the intramolecular C-C bonds are formed via cyclodehydrogenation. Currently amended
The method of claim 90, wherein n is 2 such that the aromatic core is a naphthyl and the q uinoline moieties are benzoquinoline. Currently amended
The method of claim 90, wherein the corresponding nitrogen- doped graphene nanoribbon is a nitrogen-doped N=7 armchair graphene nanoribbon. Currently amended
The method of claim 90, wherein the correspondin q polv q uinoline is a polyquinoline with a plurality of quinolines interlinked at the 4 and 6 positions. Currently amended
A method of producing nitro g en-doped g raphene seq ments comprising: reactin q an aromatic aldimine with an aromatic bialk yny l in the presence of a Lewis acid mediator and an oxidant to produce the correspondin g bi q uinoline; and formin g intramolecular C-C bonds between aromatic and heteroaromatic moieties of the correspondin q bi q uinoline to form the correspondin q nitro q en-doped g raphene seg ment, wherein: the aromatic aldimine is of formula: SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.6.svg 1 0.96 Black and white comprising: a first aromatic core comprising aromatic or heteroaromatic rings, wherein n is a number of distinct rings and is an integer of at least 1 s and the first aromatic core is optionally substituted at any of its aromatic or heteroaromatic rings with one or more functionalities each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, or any combination thereof; and an aldimine functionality attached to the first aromatic core, wherein R is an aromatic or heteroaromatic functionality optionally substituted with one or more substituents, each independently selected from the group: a halogen, an alkyl, an alkoxy, an acetyl, an N-acetyl, an amine, an alkyl amine, a sulfide, a nitrate, a nitrile, another electron withdrawing or electron SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.7.svg 0.16 4 Black and white the aromatic bi alkynyl, comprises a second aromatic core and two aromatic terminal alkyne functionalities; and SVG 15538180.09-15-2020.KF₄KS₉PORXEAPX0.CLM.8.svg 0.12 0.58 Black and white the aldimine functionalities of two molecules of the aromatic aldimine react[[s]] with the two aromatic terminal alkyne functionalities of one molecule of the aromatic bi alkynyl to yield quinoline moieties incorporating the nitrogens of the aldimine functionalities. Currently amended
The method of claim 98, wherein n is 2 such that the first aromatic core is a naphthyl, and the q uinoline moieties are benzoquinoline. Currently amended
The method of claim 98, wherein n is 2 and the ring of the first aromatic core that does not bear the aldimine functionality is heteroaromatic. Previously presented
The method of claim 98, wherein n is at least 2 and some or all of the aromatic rings of the first aromatic core are linked at the 4 and 6 positions rather than fused, such that the aromaticity of the aromatic core is maintained. Previously presented
The method of claim 98, wherein the second aromatic core is a naphthyl moiety. Previously presented
The method of claim 98, wherein n is 1, the aromatic alkynyl is 1,5-dichloro-9, 1 0-diethynylanthracene, and two intramolecular C-C bonds are formed via Heck reaction such that the correspondin q nitro g en-doped raphene se q ment i s a rubicene nitrogen-doped molecular segment. Currently amended
The method of claim 98, wherein n is 1, the aromatic alkynyl is 1,5-dichloro-9, 1 0-diethynylanthracene, and two intramolecular C-C bonds are formed via base mediated cyclodehydrogenation reaction such that the correspondin g nitro g en-doped graphene se g ment is a tetrabenzopentacene nitrogen-doped molecular segment. Currently amended
Materials described outside the worked examples.
bifunctional aromatic aldimine
aromatic mono- or bialkynyl
bi-quinoline or polyquinoline
Additional fabrication and treatment steps described in the patent.
naphthyl
benzoquinoline
phenanthroline variant quinoline
nitrogen-doped graphene nanoribbon
benzene substituted with two Cl at positions 2 and 5
phenylacetylene
rubicene nitrogen-doped molecular segment
naphthyl alkyne
tetrabenzopentacene nitrogen-doped molecular segment
1,5-dichloro-9,10-diethynylanthracene
bifunctional aromatic aldimine (self-polymerizing)
nitrogen-doped N=7 armchair graphene nanoribbon
polybenzoquinoline
aromatic aldimine (monofunctional)
naphthyl
benzoquinoline
phenanthroline variant quinoline
nitrogen-doped graphene nanoribbon
benzene substituted with two Cl at positions 2 and 5
phenylacetylene
rubicene nitrogen-doped molecular segment
naphthyl alkyne
tetrabenzopentacene nitrogen-doped molecular segment
1,5-dichloro-9,10-diethynylanthracene
bifunctional aromatic aldimine (self-polymerizing)
nitrogen-doped N=7 armchair graphene nanoribbon
polybenzoquinoline
aromatic aldimine (monofunctional)
naphthyl
benzoquinoline
phenanthroline variant quinoline
nitrogen-doped graphene nanoribbon
benzene substituted with two Cl at positions 2 and 5
phenylacetylene
rubicene nitrogen-doped molecular segment
naphthyl alkyne
tetrabenzopentacene nitrogen-doped molecular segment
1,5-dichloro-9,10-diethynylanthracene
bifunctional aromatic aldimine (self-polymerizing)
nitrogen-doped N=7 armchair graphene nanoribbon
polybenzoquinoline
aromatic aldimine (monofunctional)
naphthyl
benzoquinoline
phenanthroline variant quinoline
nitrogen-doped graphene nanoribbon
benzene substituted with two Cl at positions 2 and 5
phenylacetylene
rubicene nitrogen-doped molecular segment
naphthyl alkyne
tetrabenzopentacene nitrogen-doped molecular segment
1,5-dichloro-9,10-diethynylanthracene
bifunctional aromatic aldimine (self-polymerizing)
nitrogen-doped N=7 armchair graphene nanoribbon
polybenzoquinoline
aromatic aldimine (monofunctional)
