Synthesis of porphyrin‐end‐functionalized polycyclohexane with well‐controlled and defined polymer chain structure

Abstract

AbstractTetraphenylporphyrin‐end‐functionalized polycyclohexane (H2TPP‐PCHE) and its metal complexes (MTPP‐PCHE) were synthesized as the first successful example of porphyrin‐end‐functionalized transparent and stable polymers with a well‐controlled and defined polymer chain structure. Chloromethyl‐end‐functionalized poly(1,3‐cyclohexadiene) (CM‐PCHD) was synthesized as prerequisite prepolymer by the postpolymerization reaction of poly(1,3‐cyclohexadienyl)lithium and chloro(chloromethyl)dimethylsilane. CM‐end‐functionalized PCHE (CM‐PCHE) was prepared by the complete hydrogenation of CM‐PCHD with p‐toluenesulfonyl hydrazide. H2TPP was incorporated onto the polymer chain end by the addition of 5‐(4‐hydroxyphenyl)‐10,15,20‐triphenylporphyrin to CM‐PCHE. The complexation of H2TPP‐PCHE and Zn(OAc)2 (or PtCl2) yielded a zinc (or platinum) complex of H2TPP‐PCHE. H2TPP‐PCHE and MTPP‐PCHE were readily soluble in common organic solvents, and PCHE did not inhibit the optical properties of the H2TPP, ZnTPP, and PtTPP end groups. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011