A comparative study of solid-state oxidative cross-linking (SOC) of polynorbornylenes containing thiophene (N1T), bithiophene (N2T), and terthiophene pendants (N3T) probing polymerization ability, kinetics, and the electrochemical and optical properties of the resulting conductive polythiophene interpenetrating networks (IPN)s is reported. Generally, conductive IPNs prepared from these systems were found to exhibit the capability to shuttle ions with predominant anion transport during the doping/ dedoping process and were found to have doping levels ranging from 17 to 36%. N2T was found to produce conductive IPNs via SOC with a lower energy π to π* transition compared to those prepared from N3T.