A RATIONAL SYNTHESIS OF POLYACRYLATES WITH DISCOGENIC SIDE-GROUPS

The ferric chloride mediated oxidative coupling of 3,3',4,4'-tetrahexy loxybiphenyl with 2-hexyloxyanisole followed by demethylation gave 3,6 ,7,10,11-pentahexyloxy-2-hydroxytriphenylene. Reaction with tert-butyl dimethylsiIyl-protected 6-bromohexanol, removal of the protecting grou p, and condensation with acryloyl chloride or methacryloyl chloride ga ve acrylate and methacrylate monomers with hexamethylene 'spacers'. Al ternatively, reaction of 3,6,7,10,11-pentahexyloxy-2-hydroxytriphenyle ne with 2-(2-chloroethoxy)ethanol followed by acryloyl chloride or met hacryloyl chloride gave acrylate and methacrylate monomers with diethy lenoxy 'spacers'. Both of the poly(acrylate) homopolymers and the poly (methacrylate) homopolymer with the diethylenoxy 'spacer' gave columna r liquid crystal phases. This is contrary to the current perception th at the methacrylate polymer backbone is too inflexible to be incorpora ted in columnar phases.