Polymerization of phenylamines with a disulfide transfer reagent to yield poly[<i>N,N</i>-(phenylamino) disulfides] were investigated due to their unique bonding structures which may lead to new reactivities and conjugation along the backbone. These polymers were synthesized from nine different anilines and sulfur monochloride with triethylamine in a step-growth polymerization. The polymers were characterized by NMR, SEC-MALS and UV-Vis spectroscopy. Spectroscopic methods were employed to confirm reaction through the amine and general structure of the polymers. These polymers possess 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 solutions, while the electron rich systems gave orange, red, and even purple solutions. These colors suggest extended conjugation through the polymer since the original monomers were white and clear in solution. This supports the possibility to tune the electron density in the conjugated system which may be useful for conductivity in developing a semiconducting organic polymer or tuning chemical sensitivity to react with the backbone. Although further exploration needs to be done, preliminary studies on the ladder application showed that these polymers reacted with thiols shown by their colors rapidly disappearing in the presence of excess 2-mercapto ethanol. This suggests potential chemosensitivity to nucleophilic groups which could allow these polymers to be used as chromophoric detectors.

Synthesis and characterization of poly[<i>N,N</i>-(phenylamino) disulfide] derivatives: A sulfur rich set of polymers with adjustable color properties

ACS Spring Meeting 2021

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Synthesis and characterization of poly[N,N-(phenylamino) disulfide] derivatives: A sulfur rich set of polymers with adjustable color properties