Since the original synthesis of DPPPV, many modifications to the basic structure have been reported. Recently, the synthesis of a unique DPPPV monomer having a pendent benzyloxy substituent was completed. Thus, the alkynes 1-(benzyloxy)-4-(propargyloxy)benzene and 1-(benzyloxy)-4-(5-pentynyloxy)benzene were reacted with 2,5-di(carboethoxy)3,4-diphenylcyclopentadienone to yield the corresponding terephthalates. The terephthalates were reduced with lithium aluminum hydride to the corresponding diols which were reacted with thionyl chloride to yield the monomers 5-((4-(benzyloxy)phenoxy)propyl)- and 5-((4-(benzyloxy)phenoxy)methyl)-1,4-di(chloromethyl)-2,3-diphenylbenzene. Polymerization of the dichloro monomers via a Gilch polymerization yielded DPPPVs with pendent benzyloxy substituents. The polymers were partially soluble in chlorinated solvents and fluoresced bluish-green under UV light either in solution or in the solid state. 

Benzyloxy substituted DPPPV

247th National Meeting (2014)

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