Discotic liquid crystalline tris(hexahexyloxytriphenylene)triazines with separate columns of triphenylene and triazine cores

Abstract

A series of novel discotic liquid crystal compounds containing three pendent triphenylenes connected to a triazine core via spacers of different length that were linked via a triazole group as obtained from an azide–alkyne click reaction was investigated. All compounds of the series exhibit wide-range columnar phases from room temperature to more than 100°C. X-ray reflection measurements indicate an ordering with separate columns of the triazine and triphenylene cores. Quantum chemical calculations confirmed the significant contributions of the triazine and triazole groups to the π–π stacking in the columns. This type of organisation reveals an additional feature of triazole-forming click chemistry and indicates interesting properties for optoelectronic applications.

Keywords:

• columnar phase
• azide–alkyne click
• quantum chemistry
• trimeric

Acknowledgements

Dr M. Giesbers is thanked for help with the initial XRD measurements, F. Claassen for his help with obtaining the mass spectra and B. van Lagen for the NMR spectra.