Synthesis and Properties of Light-Emitting Polythiophene Derivatives Bearing Terphenyl Mesogenic Pendant

Abstract

A series of polythiophenes containing terphenyl mesogenic side chain at the third position through ester bonding was synthesized by dehalogenative polycondensation. The thiophene monomers 2,5-bromo-3-{[(4-(4′-cyano)terphenyloxy)carbonyl]-methyl]}-thiophene [M(CN)] and 2,5-bromo-3-{[(4-(4′-methoxy)terphenyloxy)-carbonyl]methyl}-thiophene [M(OCH3)] were prepared via Suzuki reation and esterification reactions, in sequence. The structures and properties of the monomers and polymers were characterized and evaluated with nuclear magnetic resonance, infrared spectroscopy, thermogravimetry, differential scanning calorimetry, polarized optical microscopy, ultraviolet spectroscopy, and photoluminescence. All of the polymers were stable, losing little of their weights when heated to ≥300°C. The polymers showed good solubility and could be dissolved in common solvents such as CHCl3, THF, DMF, etc. The monomers exhibited enantiotropic SmAd phases with a bilayer arrangement in the heating and cooling processes. Due to short spacer methylene ester between the bulk terphenyl mesogenic side chain and rigid polythiophene main chain, the polymers could not exhibit liquid crystallinty at elevated temperature. The existence of the chromophoric terphenyl core endows the polymers with high photoluminescence. When their CH2Cl2 solutions were photoexcited, the polymers emitted a strong UV light about 400 nm.