Diazaboroles with quinone units: hydrogen bonding network and n-type FETs involving a three-coordinate boron atom

Abstract

A series of monodiazaborole and bis(diazaborole) derivatives with a quinone moiety have been prepared as stable electron acceptors. They show dark colors in the solid states and reversible reduction potentials in the cyclic voltammograms. X-Ray structure analysis of one derivative revealed a π-stacking structure accompanied with a hydrogen-bonding network. Trifluoromethyl substituted derivatives afforded n-type FET characteristics with an electron mobility of 10⁻² cm² V⁻¹s⁻¹. An ambipolar FET characteristic was also observed in the biphenyl derivative. The planar three-coordinate boron units were used as π-linkers to afford n-type and ambipolar FET characteristics.