Synthesis, characterization and hydrolysis of aromatic polyazomethines containing non-coplanar biphenyl structures

New polyazomethines containing electron-withdrawing trifluoromethyl group and non-coplanar biphenyl structures were prepared at room temperature under reduced pressure. It was found that these polyazomethines would undergo hydrolysis in DMSO solution at temperature higher than 50 °C. The hydrolysis, evidenced by 1H NMR spectra and GPC chromatograms, was resulted from the reverse reaction of azomethine formation and was facilitated at higher temperature. The GPC results also suggested that post-polymerization would be possible if polyazomethine films were heated at elevated temperature (200 °C) under reduced pressure (0.27 torr). The HOMO (−5.69 to −5.96 eV) and LUMO (−3.04 to −3.18 eV) energy levels of the new polyazomethines are much lower than those of other polyazomethines. Combined with the excellent solubility and good thermal stability, non-coplanar biphenyl structure containing electron-withdrawing trifluoromethyl group could be a new candidate as electron acceptor for the structure design of new conjugated polymers.

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