11,11,12,12-Tetracyano-1,4-naphthaquinodimethane: a new electron acceptor

Abstract

11,11,12,12-Tetracyano-1,4-naphthaquinodimethane and related derivatives are synthesised from cis-2,3,5,8,9,10-hexahydro-1,4-naphthaquinone. As a strong electron acceptor the former forms charge-transfer complexes with aromatic hydrocarbons. Its electron affinity (1·49 eV) was obtained from charge-transfer spectra and polarography. Pertinent parameters derived by simple HMO methods are also evaluated.