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Synthesis of Mesomorphic 3,5-Bis(3,4,5-trialkyloxybenzoylamino)-4-methylbenzoates Involving Intermolecular Hydrogen Bonding

K. Roche and L. Douce*

Groupe des Matêriaux Organiques, Institut de Physique et Chimie des Matêriaux
UMR 7504 CNRS, 23 rue du Loess, F-67037 Strasbourg Cedex France

A series of methyl 3,5-bis(3,4,5-trialkyloxybenzoylamino)-4-methylbenzoates (alkyl = CH₃(CH₂)_n-1, n = 8, 10, 12, 14 and 16) exhibits mesomorphic behavior at temperatures between 120 and 240 °C. The liquid crystalline properties have been characterized using differential scanning calorimetry, optical polarization microscopy and X-ray diffraction. The molecules stack in columns which pack under hexagonal symmetry. Variable temperature infra-red absorption measurements provide evidence of intermolecular hydrogen bonding between the amide entities in both the crystalline and liquid-crystalline phases.

Keywords: Mesomorphism, Hexagonal columnar, Liquid crystal, Amide H-bonding