Electronic and electrochemical studies of 2,2-bis[5´- (2´-carbonylfuranyl)]propane: Electronic and electrochemical studies of 2,2-bis[5´-(2´-carbonylfuranyl)]propane

Abstract

The present study reports the synthesis and characterization of the compound 2,2-bis[5´- (2´- carbonylfuranyl)]propane (BCFP) which is a prototype of a building block for the preparation of macrocycles, polymers, and even supramolecular structures for different applications. The synthesis of BCFP was carried out through the Vilsmeier-Haack reaction of 2,2-bis(2’-furanyl) propane using DMF and POCl3 with a 55% yield. The compound exhibits an n  π* transition characteristic of compounds with sp2 atoms containing free nonbonding pairs. Likewise, cyclic voltammetry (CV) showed two irreversible redox processes (reduction and oxidation) which proved to be both electrochemically and chemically irreversible in nature. Theoretical calculations at the DFT level corroborated both electronic transitions and redox processes. The frontier molecular orbitals (HOMO and LUMO) were dominated by aldehyde groups and furan rings.