The Synthesis of Benzyloxy Substituted DP-PPVs

Abstract

The alkyne 1-(benzyloxy)-4-(propargyloxy)benzene was reacted with 2,5-di(carboethoxy)3,4-diphenylcyclopentadienone to yield diethyl 5-((4-(benzyloxy)phenoxy)methyl)-2,3-diphenylterephthalate. The terephthalate was reduced with lithium aluminum hydride to produce 5-((4-(benzyloxy)phenoxy)methyl)-1,4-di(hydroxymethyl)-2,3-diphenylbenzene. The diol was reacted with thionyl chloride to yield the monomer 5-((4-(benzyloxy)phenoxy)methyl)-1,4-di(chloromethyl)-2,3-diphenylbenzene that has a pendent protected phenol function. The new compounds were characterized by melting point, IR, 1H NMR, 13C NMR spectroscopy and elemental analysis. Polymerization of the dichloro monomer via a Gilch polymerization yielded poly[(2,3-diphenyl-(5-((4-(benzyloxy)phenoxy)methyl)-1,4-phenylene) vinylene]. The polymer was characterized by IR, 1H NMR spectroscopy, TGA and DSC. The polymer was insoluble in most solvents but partially soluble in chlorinated solvents. The solid polymer fluoresced a bluish-green under UV light either in solution or in the solid state