Enhancing the Acceptor Character of Conjugated Organoborane Macrocycles: A Highly Electron-Deficient Hexaboracyclophane

Angewandte Chemie
Nurcan Baser-KirazliFrieder Jäkle

Abstract

We introduce a new boron-doped cyclophane, the hexabora[16 ]cyclophane B6-F Mes, in which six tricoordinate borane moieties alternate with short conjugated p-phenylene linkers. Exocyclic 2,4,6-tris(trifluoromethyl)phenyl (F Mes) groups serve not only to further withdraw electron density but at the same time sterically shield the boron atoms, resulting in a macrocycle that is both highly electron-deficient and stable. The optical and electronic properties are compared with those of related linear oligomers and the electronic structure is further evaluated by computational methods. The studies uncover unique properties of B6-F Mes, including a low-lying and extensively delocalized LUMO and a wide HOMO-LUMO gap, which arise from the combination of a cyclic π-system, strong electronic communication between the closely spaced borons, and the attachment of electron-deficient pendent groups. The binding of small anions to the electron-deficient macrocycle and molecular model compounds is investigated and emissive exciplexes are detected in aromatic solvents.

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Citations

Jan 21, 2021·Chemical Communications : Chem Comm·Yohei AdachiJoji Ohshita
Dec 15, 2020·Chemistry : a European Journal·Yohei AdachiJoji Ohshita
Jun 11, 2021·Angewandte Chemie·Daisuke ShimoyamaFrieder Jäkle
Aug 31, 2021·Chemistry : a European Journal·Erik FilbeckHans-Jörg Himmel

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