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Fused Helicene Chains: Towards Twisted Graphene Nanoribbons
Author(s) -
Pradhan Anirban,
Dechambenoit Pierre,
Bock Harald,
Durola Fabien
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201603702
Subject(s) - helicene , intramolecular force , trimer , tetramer , regioselectivity , monomer , chemistry , stereochemistry , materials science , molecule , dimer , organic chemistry , catalysis , polymer , enzyme
By taking advantage of an unexpected regioselectivity of intramolecular Scholl reactions on pentaphenylene compounds that favors distorted [5]helicenes over their flat counterparts, a new synthetic approach to twisted graphene nanoribbons has been designed based on side‐fused di‐ tert ‐butyl‐[5]helicene fragments. Syntheses of both small monomers and dimers have been achieved and their structures have been studied. An iterative synthetic strategy has been developed for the formation of longer flexible precursors, which relies on the step‐by‐step elongation of mono‐functionalized oligomeric chains. The flexible trimer and tetramer have, thus, been synthesized and submitted to intramolecular Scholl reactions, which revealed important purification and characterization issues.