Patent ID: 11945780
Assignee: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA
Field: Organic fine chemistry (Chemistry)
Classification: CPC C | IPC C

Claim 33:
34. A method of producing nitrogen-doped graphene segments comprising:
reacting an aromatic aldimine with an aromatic mono- or bi-alkynyl in the presence of a Lewis acid mediator and an oxidant to produce the corresponding quinoline or biquinoline; and
forming intramolecular C—C bonds between aromatic and heteroaromatic moieties of the corresponding quinoline or biquinoline to form the corresponding nitrogen-doped graphene segments, wherein:
the aromatic aldimine is of formula:, 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 substituted with at least one halogen; and

an aldimine functionality immediately and covalently 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 consisting of: 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; wherein
 the at least one halogen is at meta position of the aromatic core relative to the aldimine functionality; and

the aromatic mono- or bi-alkynyl comprises a second aromatic core and one or two aromatic terminal alkyne functionalities; and wherein

the aldimine functionality of the aromatic aldimine reacts with the one or two aromatic terminal alkyne functionalities of the aromatic mono- or bi-alkynyl to yield the corresponding quinoline or biquinoline comprising quinoline moieties incorporating the nitrogens of the aldimine functionalities.