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Published on: October 3, 2018
Dinaphthooxepine Bisimide Undergoes Oxygen Extrusion Reaction upon Electron Injection at Room Temperature
Mai Odajima1, Norihito Fukui1,2, Hiroshi Shinokubo1
1Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8603, Japan.
Abstract:
We report the synthesis and properties of a dinaphthooxepine bisimide (DNOBI), a nonplanar perylene bisimide (PBI) analogue with an inserted oxygen atom. A DNOBI underwent an oxygen-extrusion reaction smoothly upon electron injection at room temperature, affording PBI in good yield. Studies on the reaction mechanism suggest that the injection of two electrons triggers the isomerization of DNOBI to dinaphthooxanorcaradiene bisimide, which is a key step in inducing the oxygen-extrusion reaction.
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