Divanillin-Based Polyazomethines: Toward Biobased and Metal-Free π-Conjugated Polymers
Guillaume Garbay, Lauriane Giraud, Sai Manoj Gali, Georges Hadziioannou, Étienne Grau, Stéphane Grelier, Éric Cloutet, Henri Cramail, Cyril Brochon
Abstract
Divanillin was synthesized in high yield and purity using Laccase from Trametes versicolor. It was then polymerized with benzene-1,4-diamine and 2,7-diaminocarbazole to form polyazomethines. Polymerizations were performed under microwave irradiation and without transition-metal-based catalysts. These biobased conjugated polyazomethines present a broad fluorescence spectrum ranging from 400 to 600 nm. Depending on the co-monomer used, polyazomethines with molar masses of around 10 kg·mol–1 and with electronic gaps ranging from 2.66 to 2.85 eV were obtained. Furthermore, time-dependent density functional theory (TD-DFT) calculations were performed to corroborate the experimental results.