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Synthesis to enhance the electron donor ability of organic radicals has not been attempted due to reactivity challenges. Herein, naphthalenediimide-based (NDI•±) zwitterionic radicals are synthesized and isolated bestowing SOMO levels… Click to show full abstract
Synthesis to enhance the electron donor ability of organic radicals has not been attempted due to reactivity challenges. Herein, naphthalenediimide-based (NDI•±) zwitterionic radicals are synthesized and isolated bestowing SOMO levels up to -4.04 eV. As a result, reduction of the NDI is realized with NDI•± radicals in their ground states. Notably, reduction of the NDI unit applying a π-electron donor is unprecedented and has been limited to inorganic/organometallic reagents or by light-driven excited states.
Journal Title: Organic letters
Year Published: 2020
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