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NIR-Absorbing π-Extended Azulene: A Non-Alternant Isomer of Terrylene Bisimide.
Angewandte Chemie International Edition ( IF 12.257 ) Pub Date : 2020-05-22 , DOI: 10.1002/anie.202005376
Frank Würthner,Bartłomiej Pigulski,Kazutaka Shoyama

The first planar π-extended azulene that retains aromaticity of odd-membered rings was synthesized by [3+3] peri-annulation of two naphthalene imides at both long-edge sides of azulene. Using bromination and subsequent nucleophilic substitution by methoxide and morpholine, selective functionalization of the π-extended azulene was achieved. Whilst these new azulenes can be regarded as isomers of terrylene bisimide they exhibit entirely different properties which include very narrow optical and electrochemical gaps. DFT, TD-DFT as well as nucleus-independent chemical shift calculations were applied to explain the structural and functional properties of these new π-scaffolds. Furthermore, X-ray crystallography confirmed planarity of reported π-scaffolds and aromaticity of their azulene moiety.
更新日期:2020-05-22

 

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