Photoelectroactive Corrole Monomer Functionalized with a Triphenylamine–Chalcone Derivative: Synthesis, Electropolymerization, and Electrochromic Applications

Abstract

In this work, we report the divergent synthesis of a novel corrole macrocycle with a Tshaped geometry, functionalized with triphenylamine (TPA) units. The synthetic route involved a green preparation of 5-(pentafluorophenyl)dipyrromethane, condensation with pentafluorobenzaldehyde, and DDQ oxidation to afford the target corrole. In parallel, a TPA-based chalcone derivative was obtained and introduced via regioselective nucleophilic aromatic substitution. The resulting photoactive corrole–TPA conjugate exhibited efficient electropolymerization, retaining the corrole chromophore while forming conductive TPB-linked films (TPB, tetraphenylbenzidine). Spectroelectrochemical studies confirmed reversible redox activity, color switching, and electrochromic behavior, highlighting its potential as a building block for photo- and electroactive devices.