Premium
Octafunctionalized Biphenylenes: Molecular Precursors for Isomeric Graphene Nanostructures
Author(s) -
Schlütter Florian,
Nishiuchi Tomohiko,
Enkelmann Volker,
Müllen Klaus
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201309324
Subject(s) - biphenylene , helicene , aryne , graphene , cycloaddition , chemistry , nanostructure , annulene , nanotechnology , combinatorial chemistry , stereochemistry , materials science , molecule , organic chemistry , catalysis , phenylene , polymer
A straightforward method for the octafunctionalization of biphenylene based on the [2+2]‐cycloaddition of an aryne intermediate has been developed. This enabled a “North–South” extension of biphenylene towards isomeric graphene nanoribbons composed of four‐, six‐, and eight‐membered rings. This procedure furthermore allowed an “East–West” expansion to [ n ]phenylenes with different lengths. For the fabrication of isomeric nanongraphenes, octaarylbiphenylenes decorated with phenyl, pyrenyl, and thieno substituents were prepared. The subsequent oxidative cyclodehydrogenation provided an expanded helicene as a model compound.