Solvothermal Polymerization of Diaminomaleonitrile Reveals Optimal Green Solvents for the Production of C=N-Based Polymers
2024
Solvothermal polymerization (STP) of diaminomaleonitrile (DAMN) was evaluated using a wide variety of solvents and in the temperature range from 80 to 170 °C. The highest yields, almost quantitative, were achieved with protic n-alcohols such as n-pentanol or n-hexanol at 130 and 150 °C, respectively. The kinetic behavior was studied by gravimetry and the DAMN consumption was monitored by UV-vis spectroscopy and HPLC. GC-MS identified byproducts of the DAMN hydrolysis and oxidation reactions, which were significantly reduced when n-pentanol or n-hexanol were used with respect to hydrothermal conditions. This led to an exploration of compositional changes and microstructural variations by FTIR and NMR spectroscopy and simultaneous thermal analysis. n-Hexanol appears to be an ideal eco-friendly solvent for the DAMN self-STP. The results presented here are not only of interest for the design of polymeric materials based on C=N structures but also show remarkable implications for prebiotic chemistry.
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