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Five new unsymmetric thiophene imines end-capped with an electron-donating amine (−NH2) group were obtained using a simple synthetic route, that is, the melt condensation of 2,5-diamino-thiophene-3,4-dicarboxylic acid diethyl ester with commercially available aldehydes. Their thermal stability and electrochemical and photophysical (absorption (UV−vis) and photoluminescence (PL)) properties were examined and density functional theory calculations were performed. The imines were thermally stable above 200 °C. They underwent reduction and oxidation processes and exhibited an energy band gap electrochemically estimated between 1.81 and 2.44 eV. They absorbed radiation from the UV and visible range to 480 nm and showed weak light emission. These compounds were investigated as hole transporting materials in solar cells with the structure FTO/b-TiO2/m-TiO2/perovskite/imine/Au. The highest photoelectric conversion efficiency was observed for compounds with a morpholine derivative substituent.

Title: New thiophene imines acting as hole transporting materials in photovoltaic devices