Synthesis and characterization of high molecular weight phthalocyanine-PPV copolymers through post-polymerization functionalization

Abstract

High molecular weight poly(p-phenylenenevinylene) PPV copolymers laterally substituted with zinc (II) phthalocyanines (Zn(II) Pc-PPV 1 and 2) have been synthesized by means of post-polymerization functionalization reactions through DCC-mediated esterifications between hydroxy-phthalocyanines 4 and 6 and carboxy-bearer PPV copolymers, comprising 2-methoxy-5-(3,7-dimethyloctyloxy)-1,4-phenylene-vinylene (MDMO-PPV) and 1,4-(2-(5-carboxypentyloxy)-5-methoxyphenylenevinylene (CPM-PPV) units in a 9: 1 (3) and 1: 1 (5) ratio, respectively. The resulting copolymer 1 contains a 7 mol % of Pc molecules, while copolymer 2, which is isolated as the soluble fraction of the reaction with the starting 1: 1 copolymer (namely having around 50% of COOH-containing monomeric units), holds a 9 mol % of zinc(II) phthalocyanines. 1 and 2 were fully characterized by (1)H NMR, UV-vis and FT-IR spectroscopies.