SYNTHESIS OF HIGHLY PHENYLATED POLY(P-PHENYLENEVINYLENES) VIA A CHLORINE PRECURSOR ROUTE

The synthesis of several highly phenylated poly(p-phenylenevinylene) ( PPV) derivatives by a chlorine precursor route was investigated in ord er to understand its scope. Three 1,4-bis(chloromethyl)benzene monomer s were prepared via a robust and versatile synthetic procedure involvi ng the Diels-Alder reaction. In the presence of 1.1 equiv of potassium tert-butoxide, the monomers underwent 1,6-dehydrochlorination to form the respective xylylenes which underwent 1,6-polymerization to give t he corresponding chlorine precursor polymers. The 1,6-polymerization m echanism of the highly phenylated monomers is discussed. Only one mono mer gave a soluble precursor polymer while the other two gave insolubl e precursor polymers. The soluble precursor polymer was deposited as t hin films and then converted to the corresponding PPV derivative, whic h showed green photoluminesence and electroluminesence.