Schiff bases containing triphenylamine and pyrrole units: synthesis and electrochromic, acidochromic properties

Abstract

Five Schiff bases (SBs) containing pyrrole and different triphenylamine (TPA) moieties were synthesized and the structures were confirmed by infrared spectroscopy (IR) and the nuclear magnetic resonance (NMR) technique. SB1 exhibited intense fluorescence emission in contrast to SB2–SB5. The electrochemical behaviors of the SBs were investigated by the cyclic voltammetry (CV) technique. SB2–SB5 exhibited redox stability with one well-defined and reversible redox couple upon electrochemical oxidation. On the contrary, SB1 revealed two oxidation peaks and one reduction peak in the first CV curve, followed by four well-defined redox couples in the steady-state CV curves. Electrochromic behaviors of the SBs have been observed, accompanied with a new absorption peak appearing with obvious color change from pale yellow neutral form to red oxidation form. SB1–SB5 also displayed sensitive acidochromic behaviors, and a linear dependence of maximum absorption wavelength as a function of pH values has been observed which proved the SBs could be used as alternative pH sensors in the given range.