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

نویسندگان

  • Johannes Holzwarth
  • Konstantin Yu Amsharov
  • Dmitry I Sharapa
  • David Reger
  • Kateryna Roshchyna
  • Dominik Lungerich
  • Norbert Jux
  • Frank Hauke
  • Timothy Clark
  • Andreas Hirsch
چکیده

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.

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عنوان ژورنال:

دوره 56  شماره 

صفحات  -

تاریخ انتشار 2017