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Paper | Regular issue | Vol 83, No. 5, 2011, pp.1057-1065
Published online, 28th March, 2011
DOI: 10.3987/COM-11-12155
Synthesis and Mesomorphic Properties of a Series of Phenyl 6-(4-Alkoxyphenyl)nicotinates

Win-Long Chia* and Cheng-Yao Tsai

*Department of Chemistry, Fu Jen Catholic University, Taipei, Taiwan 24205, Taiwan, R.O.C.

Abstract

A new homologous series of phenyl 6-(4-alkoxyphenyl)nicotinates (nOPNicP, n = 3-7) was synthesized. The entire synthetic procedure was completed in a short two-step process. Very good two-step overall yields of 70-80% were obtained and high α–regioselective addition of Grignard reagents to 1-acylnicotinium salts was observed while preparing this series of liquid crystals. Spectral analyses were in accordance with the expected structures. Their thermotropic behaviours were studied using polarizing optical microscopy and further confirmed by differential scanning calorimetry. Smectic A phase was found to be the only mesophase in this series of compounds.