The Synthesis, Characterization, and Iodine Doping of a Soluble Polyazine: The Propyl-Methyl Substituted Derivative
William B. Euler, Chemistry of Materials, 1990, 2, 209 – 213
Abstract
Reaction of 2,3-hexanedione with 2,3-hexanedione dihydrazone leads to a polyazine that is soluble in organic solvents. This synthetic method gives a polymer with statistically alternating methyl and propyl substituents on the carbon atoms along the chain. Like the previously reported permethylpolyazine, IR spectra suggest that the propyl methyl polymer is a linear chain with double bonds in the E conformation and single bonds in the anti (or s-trans) conformation. IR, UV-vis, and NMR spectra all imply that extensive conjugation exists along the polymer backbone. The high resolution 13C NMR spectrum shows the presence of two types of sequences of propyl and methyl groups along the polymer chain. Iodine doping of this polyazine leads to a charge-transfer product with no measurable electrical conductivity. An iodine titration of the polymer allows an estimation of the equilibrium constant for the charge-transfer reaction of 800 M–1.