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Highly Electron-Deficient Dicyanomethylene-Functionalized Triarylboranes with Low-Lying LUMO and Strong Lewis Acidity

Guanming Liao, Xing Chen, Yali Qiao, Kanglei Liu, Nan Wang, Pangkuan Chen, Xiaodong Yin

2021Organic Letters21 citationsDOI

Abstract

A series of dicyanomethylene-functionalized triarylboranes is reported in this work, with low-lying LUMO energy levels at ca. −3.66 eV for FMesB-ACN. The single-crystal structures of the mono- and dianion of Mes*B-ACN were obtained via chemical reduction, which revealed a conversion from a quinoidal to an aromatic structure. The strong Lewis acidity of these compounds is reflected in a fluoride-anion binding experiment. This work introduces a facile strategy for modulating the electron deficiency of boron-containing compounds.

Topics & Concepts

ChemistryHOMO/LUMOBoronLewis acids and basesFluorideFluorineIonElectronPhotochemistryInorganic chemistryMoleculeCatalysisOrganic chemistryQuantum mechanicsPhysicsOrganoboron and organosilicon chemistryLuminescence and Fluorescent MaterialsCrystallography and molecular interactions
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