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Complexation-Triggered Fluctuation of π-Conjugation on an Antiaromatic Dicyanoanthracene Dianion
Taiki Imagawa1, Kazuki Okazawa2, Kazunari Yoshizawa2
1Department of Chemistry, Graduate School of Advanced Engineering and Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi, Hiroshima, 739-8526, Japan.
Abstract:
The formation of Lewis pairs is an important chemical concept. Recently, the complexation of Lewis acidic tris(pentafluorophenyl)borane with Lewis basic moieties and subsequent reduction has emerged as a fascinating strategy for designing novel reactions and structures. The impact of the complexation and subsequent reduction of antiaromatic systems bearing Lewis base moieties has been investigated. We found how Lewis adduct formation stabilizes an antiaromatic system consisting of 9,10-dicyanoanthracene and tris(pentafluorophenyl)borane by using synthesis, X-ray crystallography, spectroscopic analysis, and quantum chemical calculations.
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