Main Chain Alkoxy Substituted PPV

Abstract

In the interest of the synthesis of polymers that have the potential to possess inherent light emitting properties (LEDs) the synthesis of diethyl 5-benzyloxy-2,3-diphenylbenzenecarboxylate was conducted to produce an intermediate in the synthetic pathway for a novel 1,4- bis(chloromethyl)benzene monomer. The synthesis began with production of diethyl 5-([N- methyliminodiacetato-O,O’,N]borane)-2,3- diphenylterephthalate, via a Diels-Alder reaction, using 2,5-dicarboethoxy-3,4- diphenylcyclopentadienone and ethynylboronic acid MIDA ester as starting reagents. The diester was de-boronated and oxidized to diethyl 5- hydroxy-2,3-diphenylterephthalate through a reaction with sodium carbonate and 30% hydrogen peroxide. Synthesis of diethyl 5- benzyloxy-2,3-diphenylbenzenecarboxylate was achieved through a Williamson ether synthesis involving diethyl 5-hydroxy-2,3- diphenylterephthalate and benzyl chloride. The products of each synthetic step were analyzed by 1H NMR.