Tetraphenylporphyrin-end-functionalized polycyclohexane (H(2)TPP-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. H(2)TPP was incorporated onto the polymer chain end by the addition of 5-(4-hydroxyphenyl)-10,15,20-triphenylporphyrin to CM-PCHE. The complexation of H(2)TPP-PCHE and Zn(OAc)(2) (or PtCl(2)) yielded a zinc (or platinum) complex of H(2)TPP-PCHE. H(2)TPP-PCHE and MTPP-PCHE were readily soluble in common organic solvents, and PCHE did not inhibit the optical properties of the H(2)TPP, ZnTPP, and PtTPP end groups. (C) 2011 Wiley Periodicals, Inc. J PolymSci Part A: Polym Chem 49: 5322-5329, 2011