Polymerization of Aniline Derivatives to Yield Poly[N,N-(phenylamino)disulfides] as Polymeric Auxochromes.

Polymerizations of phenylamines with a disulfide transfer reagent to yield poly[N,N-(phenylamino) disulfides] (poly-NADs) were investigated due to their unique repeat units that resulted in conjugation along the backbone that was perturbed by the aromatic rings and gave different colors for the polymers. These polymers were synthesized from 10 different anilines and sulfur monochloride in a step-growth polymerization. The polymers were characterized by nuclear magnetic resonance spectroscopy, size exclusion chromatography-multiangle light scattering, and UV-vis spectroscopy. These polymers possessed a polymeric backbone solely consisting of nitrogen and sulfur [-N(R)SS-], which was conjugated and yielded polymers of moderate molecular weight. Most notably, these polymers were an array of colors ranging from pale yellow to a deep purple depending on the substitution of the aromatic ring. The more electron-poor systems produced lighter yellow polymers, while the electron-rich systems gave orange, green, red, and even purple polymers.