Novel aspects of a convenient synthesis and of electroproperties of derivatives based on diphenylamine

The substituted monomers 4a,c,d, 5a,b, 6a, 7a,b, and 8a of novel poly(diphenylamines), possessing the respective photochromic groups, were synthesized by the Stille cross-coupling methodology (Scheme). The hyperbranched structures were characterized by ¹H- and ¹³C-NMR spectroscopy. The obtained monomers show good stability in common organic solvents such as CHCl₃, toluene, and CH₂Cl₂, and exhibit excellent thermal stability. Electrochemical results and theoretical calculations suggest that oxidation and reduction of the monomers start from the side of the amine function and the five-membered heterocyclic ring moieties, respectively.