Synthesis of fluoro substituted quaterphenyl liquid crystals

Abstract

The improved approaches for the preparation of four ring quaterphenyl liquid crystalline compounds possessing fluoro substituted moieties have been developed. The key stage for the most synthetic schemes was the preparation of 3,6-diarylsubstituted cyclohex-2-en-1-ones via condensation of the corresponding aromatic Mannich salts with the fluoro substituted methyl benzyl ketone in the presence of base. The chlorination of these cyclohexenones with phosphorous pentachloride or methylation with methylmagnesium iodide followed oxidative aromatization allows the synthesis of final four ring fluoro substituted quaterphenyl liquid crystal (LC) compounds. Another approach provides for the condensation synthesis of bromo substituted intermediate terphenyls. They have been undergoing catalytic cross-coupling with the corresponding fluoro substituted phenyl boronic acid giving a wide range of quaterphenyl LC derivatives.

Keywords:

• liquid crystal
• synthesis
• 3,6-disubstituted cyclohex-2-en-1-ones
• quaterphenyl derivatives
• phase transition