Poly(N-alkyl-3,6-dihydroxy-2,7-carbazole) which should be soluble and have phenolic function was synthesized through different two routes. The former method was a direct synthesis by polymerizing a 2,7-dibromo-3,6-dihydroxycarbazole monomer using Ni(cod)(2), which only gave a low molecular weight polymer. The latter method was an ether cleavage reaction of methoxy groups in a precursor polymer, poly(3,6-dimethoxycarbazole), using BBr3, which gave successfully the objective polymer that has a number average molecular weight of 4300 g/mol comparable to the precursor polymer. They showed large spectral changes in photoabsorption and fluorescence on addition of base. They also showed redox behavior similar to a hydroquinone/benzoquinone couple investigated by cyclic voltammetry. These new functions could be derived from the phenolic hydroxy group in the carbazole unit. (C) 2018 Wiley Periodicals, Inc.