The synthesis of seven new aromatic diisocyanide monomers is described and a rationale for their stability is given, as well as their behavior in the palladium-mediated aromatizing polymerization yielding helically chiral poly(quinoxalin-2,3-diyl)s (PQs). Acceleration of the otherwise slow polymerization by microwave heating was observed. The polymers are designed to display potential organocatalytically active functionalities (e.g., phenols, pyridines) nearby stereolabile biaryl axes, which are asymmetrically governed by the configurationally stable helical backbone. (C) 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 4830-4839, 2009