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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
A naphthalene with unusual bond alternation made by annelation with bicyclo[2.1.1]hexene units: aromaticity and
Takayuki Uto1, Tohru Nishinaga, Akira Matsuura
1Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.
Abstract:
An entirely new naphthalene having one six-membered ring, whose bond lengths are equalized, and another ring, whose bond lengths are alternated, has been prepared via one-electron oxidation of a benzene annelated with three bicyclo[2.1.1]hexene units. The structure has been determined by X-ray crystallography and the aromaticity of two benzene rings estimated by theoretical calculations. Although the former six-membered ring has a higher degree of aromaticity, it has been found to be more reactive toward singlet oxygen owing to the greater strain contained in it. These results have been interpreted by means of theoretical calculations.
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