Synthesis of novel arylamine containing perfluorocyclobutane and its electrochromic properties

A new electrochromic oligomer based on an arylamine compound containing a perfluorocyclobutane (PFCB) ring has been synthesized via 2 + 2 cyclodimerization. A new N,N,N′,N′-tetraphenyl-biphenyl-4,4′-diamine (TPD) with PFCB (TPD-PFCB) showed high thermal stability with a decomposition temperature (Td) of 435 °C. Cyclic voltammograms of TPD-PFCB films coated onto an indium–tin oxide substrate showed two reversible redox steps during a potential scan between 0.7 and 1.2 V. The spectroelectrochemical series of TPD-PFCB films exhibited color change from colorless to yellow and then to greenish blue during the oxidation reaction of TPD-PFCB. This oligomer exhibited a high electrochromic coloration efficiency (602 cm2/C) and a comparable response speed (coloring and bleaching time at 700 nm were 0.71 and 0.12 s, respectively).