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Columnar Liquid‐Crystalline Dibenzopentacenodithiophenes by Photocyclization
Author(s) -
Cabral Marilia G. Belarmino,
Pereira de Oliveira Santos Deise M.,
Bentaleb Ahmed,
Hillard Elizabeth A.,
Cristiano Rodrigo,
Gallardo Hugo,
Durola Fabien,
Bock Harald
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.201600773
Subject(s) - mesophase , thiophene , perylene , alkyl , chemistry , photochemistry , homo/lumo , columnar phase , liquid crystal , crystallography , organic chemistry , materials science , molecule , optoelectronics , phase (matter)
The twofold glyoxylic Perkin reaction of perylene‐3,9‐diglyoxylic acid with thiophene‐diacetic acid followed by oxidative photocylization and reaction with α‐branched primary alkylamines yields columnar liquid‐crystalline diimides with two sulfur atoms in the condensed arene system. A broad temperature range of the hexagonal columnar mesophase is induced by racemic doubly branched alkyl chains. The HOMO and LUMO energy levels of these thiophene‐derived diimides qualify them as electron donors with respect to perylene diimides.