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Highly Regioselective Alkylation of Hexabenzocoronenes: Fundamental Insights into the Covalent Chemistry of Graphene.

ABSTRACT: Hexa-peri-hexabenzocoronides (HBC) was successfully used as a model system for investigating the complex mechanism of the reductive functionalization of graphene. The well-defined molecular HBC system enabled deeper insights into the mechanism of the alkylation of reductively activated nanographenes. The separation and complete characterization of alkylation products clearly demonstrate that nanographene functionalization proceeds with exceptionally high regio- and stereoselectivities on the HBC scaffold. Experimental and theoretical studies lead to the conclusion that the intact basal graphene plane is chemically inert and addend binding can only take place at either preexisting defects or close to the periphery.

SUBMITTER: Holzwarth J

PROVIDER: S-EPMC5638083 | biostudies-other | 2017 Sep

REPOSITORIES: biostudies-other

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Highly Regioselective Alkylation of Hexabenzocoronenes: Fundamental Insights into the Covalent Chemistry of Graphene.

Holzwarth Johannes J Amsharov Konstantin Yu KY Sharapa Dmitry I DI Reger David D Roshchyna Kateryna K Lungerich Dominik D Jux Norbert N Hauke Frank F Clark Timothy T Hirsch Andreas A

Angewandte Chemie (International ed. in English) 20170823 40

Hexa-peri-hexabenzocoronides (HBC) was successfully used as a model system for investigating the complex mechanism of the reductive functionalization of graphene. The well-defined molecular HBC system enabled deeper insights into the mechanism of the alkylation of reductively activated nanographenes. The separation and complete characterization of alkylation products clearly demonstrate that nanographene functionalization proceeds with exceptionally high regio- and stereoselectivities on the HBC ...[more]

PMID: 28782166

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