DFT analysis and synthesis of anthracene analogues via zirconocene-mediated dimerization of boron-centered precursors

Abstract

Photovoltaics, light-emitting devices, and organic electronics all depend on carbon π-conjugated systems with boron and nitrogen. A crucial molecule in π-conjugated materials, 9,10-dihydro-9,10-diboraanthracene (DBA) is usually produced from dihalogenated precursors, but its B–C bonds are weak. A novel technique employs bulky aryl substituents to provide steric shielding for the reactive boron centers during dimerization in non-halogenated precursors containing diphenyl zirconocene and aryl bromoboranes. This provides a new method for creating diboranthene compounds and yields stable DBA counterparts. DFT calculations have corroborated the rationale of the chemical pathway.