Proton transport (PT) plays an important role in many biological processes as well as in materials for renewable energy devices. Gaining insights into functional group requirements for PT would aid the design of new materials that provide enhanced proton conduction. In this report, we outline our efforts to understand the most probable proton conduction pathway in 1H-1,2,3-triazole systems. In triazole-based systems, both imidazole- and pyrazole-like pathways are possible. By systematically comparing structurally analogous polymers based on N-heterocycles and benz-N-heterocycles, we find that the imidazole-like pathway makes a significant contribution to the proton transfer in 1H-1,2,3-triazole systems, while the contribution from pyrazole-like pathway is negligible. (C) 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 1851-1858, 2010