Pentaalkoxytriphenylene monoesters and their dyads; structural factors influencing columnar and nematic mesophase behaviour

Ester linkages are frequently employed in the design of discotic liquid crystals, and indeed the first examples of discotic liquid crystals reported by Chandrasekhar, Sadashiva and Suresh were hexaesters of benzene. Within the wide range of liquid crystalline triphenylene systems so far reported, the symmetrical hexa(aryl) esters are particularly noteworthy because they form the relatively rare and technologically important discotic nematic mesophase. An alternative strategy for inducing nematogenic behaviour is to build linked and twinned structures, and here we report examples of materials that combine the two design features. Pentahexyloxy triphenylenes bearing a single aryl ester retain the columnar mesophase. Linked dyad structures promote nematic phase formation and stability is influenced by the link type and bonding arrangement within isomeric series (phthalates) and related constructs.