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Journal of the American Chemical Society

For many years, organoboron compounds have been expected to show excellent electron-injecting and -transporting properties. However, lowest unoccupied molecular orbital (LUMO) energy levels (ELUMO) of B-containing π-conjugated molecules are mostly higher than -4.0 eV and their electron mobilities are usually less than 10-2 cm2 V-1 s-1. In this work, we experimentally prove the remarkably high electron affinity and high electron mobility of organoboron compounds. Our strategy is to incorporate multiple boron-nitrogen coordination bonds (B←N) into azaacenes. We synthesized quadruply B←N-fused dibenzo-azaacene (QBNA) through one-pot multifold borylation cyclization reaction. The incorporation of four B←N units greatly changes the electronic structures and properties and significantly downshifts the electronic energy levels of QBNA. QBNA shows a ELUMO of as low as -4.58 eV, which is among the lowest for n-type organic semiconductors. Single-crystal organic field-effect transistors of QBNA display unipolar n-type ...

Quadruply B←N-Fused Dibenzo-azaacene with High Electron Affinity and High Electron Mobility