An investigation into the preparation of poly(9-alkyl-9H-carbazole-3,6-diyl)s with palladium catalyzed cross-coupling reactions of 3-halo-6-halomagnesio-9-alkyl-9H-carbazoles, generated in situ from their corresponding 3,6-diiodo- and 3,6-dibromo-derivatives was undertaken. Monomers with a range of alkyl group substituents with different steric requirements were investigated and their effects on the polymerization were studied. The effects of the nature of halogen substituents on the polymerization reaction were also investigated. Structural analysis of the polymers revealed exclusive 3,6-linkage between consecutive carbazole repeat units on the polymer chains. The physical properties of these polymers were investigated with spectroscopic, thermal gravimetric analysis, and electrochemical studies. (C) 2004 Wiley Periodicals, Inc.