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Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling.


ABSTRACT: Nanographenes, namely polycyclic aromatic hydrocarbons (PAHs) with nanoscale dimensions (>1?nm), are atomically precise cutouts from graphene. They represent prime models to enhance the scope of chemical and physical properties of graphene through structural modulation and functionalization. Defined nitrogen doping in nanographenes is particularly attractive due to its potential for increasing the number of ?-electrons, with the possibility of introducing localized antiaromatic ring elements. Herein we present azomethine ylide homocoupling as a strategy to afford internally nitrogen-doped, non-planar PAH in solution and planar nanographene on surfaces, with central pyrazine rings. Localized antiaromaticity of the central ring is indicated by optical absorption spectroscopy in conjunction with theoretical calculations. Our strategy opens up methods for chemically tailoring graphene and nanographenes, modified by antiaromatic dopants.

SUBMITTER: Wang XY 

PROVIDER: S-EPMC5717246 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature

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Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling.

Wang Xiao-Ye XY   Richter Marcus M   He Yuanqin Y   Björk Jonas J   Riss Alexander A   Rajesh Raju R   Garnica Manuela M   Hennersdorf Felix F   Weigand Jan J JJ   Narita Akimitsu A   Berger Reinhard R   Feng Xinliang X   Auwärter Willi W   Barth Johannes V JV   Palma Carlos-Andres CA   Müllen Klaus K  

Nature communications 20171205 1


Nanographenes, namely polycyclic aromatic hydrocarbons (PAHs) with nanoscale dimensions (>1 nm), are atomically precise cutouts from graphene. They represent prime models to enhance the scope of chemical and physical properties of graphene through structural modulation and functionalization. Defined nitrogen doping in nanographenes is particularly attractive due to its potential for increasing the number of π-electrons, with the possibility of introducing localized antiaromatic ring elements. He  ...[more]

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