pi-Conjugated poly(3-nitropyridine-2,5-diyl) (PPy-3-NO2), poly(3,3'-dinitro-2,2'-bipyridine-5,5-diyl) (PBpy-3,3'-diNO(2)), and a poly(arylene ethynylene) type polymer consisting of a 3,3'-dinitro-2,2'-bipyridine unit (PAE-1) were synthesized by Cu-promoted Ullmann coupling reaction and Pd-catalyzed coupling reaction. PPy-3-NO2 and PAE-1 were soluble in organic solvents such as DMSO, DMF, and chloroform, and gel permeation chromatography analysis showed a number average molecular weight (M-n) of 9,300 and 12,300, respectively. PPy-3-NO2 gave intrinsic viscosity, [eta], of 0.53 dL g(-1) in DMF. PBpy-3,3'-diNO(2) had somewhat lower solubility. The polymers exhibited a UV-vis peak at about 430 nm. PPy-NO2 received electrochemical reduction at -1.5 V versus Ag+/Ag in acetonitrile, and gave an electrochemical redox cycle in a range from 0 to -1.1 V versus Ag+/Ag in an aqueous solution. (c) 2006 Wiley Periodicals, Inc.