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Self‐Assembly of Board‐Shaped Diketopyrrolopyrrole and Isoindigo Mesogens into Columnar π‐π Stacks
Author(s) -
Taing Hi,
Cassar Adam Michael,
Ocheje Michael Udunyi,
RondeauGagné Simon,
ElAssaad Tarek H.,
Sharabati Christa A.,
Kaafarani Bilal R.,
Eichhorn S. Holger
Publication year - 2019
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201800524
Subject(s) - stacking , materials science , supramolecular chemistry , organic semiconductor , self assembly , crystallization , thiophene , crystallography , acceptor , organic electronics , electron acceptor , discotic liquid crystal , columnar phase , liquid crystalline , nanotechnology , liquid crystal , optoelectronics , chemistry , organic chemistry , crystal structure , transistor , physics , condensed matter physics , voltage , quantum mechanics
Diketopyrrolopyrrole and isoindigo are commercially important dyes that have recently found broad application as electron acceptor and light‐absorbing groups in organic semiconductors. Their self‐assembly into specific supramolecular structures to control optoelectronic properties has been hampered by limited options for substitution and their high propensity for crystallization. Reported here is a molecular design that directs self‐assembly into previously elusive columnar mesophases of π‐π stacking cores. Although attachment of bis(trisoctyloxyphenyl)‐1,3,5‐triazine groups to both ends of diketopyrrolopyrrole‐thiophene and isoindigo cores generated mesomorphic dyes of similar overall shapes and dimensions, distinct differences in their mesomorphism and optoelectronic properties were observed.