Regioregular and Regioirregular Poly(p-phenylene)s via Ni(0)-Catalyzed Homocoupling of Arylene Bismesylates

摘要: Head-to-head regioregular poly(p-phenylene)s (PPPs) were synthesized via Ni(0)-catalyzed polymerization of 2,2‘-disubstituted 4,4‘-bis[(methylsulfonyl)oxy]biphenyls (9). The corresponding regioirregular PPPs prepared by the homopolymerization 2-substituted 1,4-bis[(methylsulfonyl)oxy]benzenes (6) and copolymerization 6 with 9. precursors 9, i.e., 1,4-dihydroxybenzene (5) 4,4‘-dihydroxybiphenyl (8), a synthetic method elaborated previously in our laboratory [J. Org. Chem. 1995, 60, 1066]. are crystalline insoluble (except when substituent is 4-tert-butylbenzoyl) while polymers noncrystalline soluble. highest molecular weight PPP was obtained 1:1 ratio influence size electronic properties on reactivity monomers 6...