Octafunctionalized Biphenylenes: Molecular Precursors for Isomeric Graphene Nanostructures | Zendy

Schlütter Florian | Zendy; Nishiuchi Tomohiko | Zendy; Enkelmann Volker | Zendy; Müllen Klaus | Zendy

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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.

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