Investigation into the molecular and electronic structures of a newly synthesized o-quinone derivative

Abstract We studied on the geometric and electronic structures of a newly synthesized compound, 3-( tert -butyl)dinaphtho[1,2- b ;1′,2′- d ]furan-12,13-dione ( 1 ), having a twisted molecular structure at an o -quinone region in a crystal. The density functional theory (DFT) has been applied to investigate the geometric and electronic structures using the model compound ( 1H ), where a tertiary butyl group of the compound 1 is replaced by a hydrogen atom. The optimized geometry for the model dimer of 1H represented well the twisted molecular structure of 1 . The time-dependent DFT method explained the observed optical properties of 1 in a solution and a powdery solid. The DFT calculations also gave a good estimation of the ionization potential and the electron affinity of 1H , explaining a similarity in reduction and a difference in oxidation between 1H and o -benzoquinone. This similarity in the electron affinity was confirmed by measuring a reduction potential of the compound 1 with cyclic voltammetry.