Liquid Crystalline Compounds in the Thiophene Series, Part 6+ Synthesis and Characterization of Azomethines and Vinylenes with Two Mesogenic Groups and Different Alkylene Spacer Lengths

Abstract

Compounds which have two mesogenic groups with and without terminal alkyl chains containing thiophene systems, were prepared from α.ω-bis(5-formyl-2-thienyl)alkanes (3a-3n) and various aromatic amines or 2-fluorenyl-Wittig-salt (10). The liquid crystalline properties of these compounds were characterized by differential scanning calorimetry (DSC) and polarizing microscopy. Only the series of α.ω-bis{5-[N-(4′-butyloxybiphenyl-4-yl)imino]formyl-2-thienyl}alkanes (7a-71) showed enantiotropic smectic and nematic mesophases. The series of E,E-α.ω-bis[5-(2-fluorenylvinyl)-2-thienyl]alkanes (8a-81) showed enantiotropic nematic mesophases for the compounds with 4 and 6 methylene groups, monotropic nematic mesophases for the compounds with 7—12 methylene groups and no liquid crystalline phases for compounds with 3, 5, 16 methylene groups in the connecting alkylene chain. In contrast to the compounds 8a-81, E-l-(5-butyl-2-thienyl)-2-(2-fluorenyl)ethylene has a smectic mesophase.