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Symmetrical and Nonsymmetrical Liquid Crystalline Oligothiophenes: Convenient Synthesis and Transition‐Temperature Engineering
Author(s) -
Leroy Julie,
Boucher Nicolas,
Sergeyev Sergey,
Sferrazza Michele,
Geerts Yves Henri
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600850
Subject(s) - chemistry , thermotropic crystal , alkyl , desymmetrization , alkylation , stacking , carbanion , terzaghi's principle , stereochemistry , crystallography , polymer chemistry , enantioselective synthesis , organic chemistry , liquid crystalline , polymer , catalysis , excavation , archaeology , history
Two approaches to transition‐temperature engineering in liquid crystalline oligothiophenes are described: (i) substitution at the aromatic core with two identical branched alkyl chains and (ii) desymmetrization of the molecule with two alkyl substituents of different length or structure. Key steps in the synthesis of symmetrical and nonsymmetrical terthiophenes and quaterthiophenes involve Suzuki coupling and carbanion alkylation. A well‐adjusted balance between the π–π stacking of the aromatic core and the disorder caused by the peripheral alkyl chains is demonstrated to be important for the control of the thermotropic behavior of oligothiophene mesogens. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)