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Paper | Regular issue | Vol 75, No. 2, 2008, pp.375-382
Published online, 2nd November, 2007
DOI: 10.3987/COM-07-11224
Facile Synthesis of a Series of 2-(4-Alkyloxyphenyl)-5-cyanopyridine Liquid Crystalline Compounds

Win-Long Chia* and Yu Wei Cheng

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

Abstract

This study describes the facile synthesis of a homologous series of pyridine-containing liquid crystalline 2-(4-alkyloxyphenyl)-5-cyanopyridines (nOPPyCN, n = 3-7). The subject liquid crystals were prepared in a short two-step reaction. First, 4-alkyloxyphenylmagnesium bromides were added to N-phenyloxycarbonyl-3- cyanopyridinium chloride, affording a 1,2-dihydropyridine, which was then oxidized by o-chloronil. The resulting products, 2-(4-alkyloxyphenyl)-5-cyanopyridines, were obtained in good yields (72%-83%). Thermotropic behaviors of these liquid crystals were investigated using differential scanning calorimetry (dsc) and polarized optical microscopy (pom).