Synthesis of Stable, High-SOMO Zwitterionic Radicals: Enabling Intermolecular Electron Transfer between Naphthalenediimides.

Org Lett

Supramolecular and Material Chemistry Lab, School of Physical Sciences, Jawaharlal Nehru University, New Delhi 110067, India.

Published: August 2020

AI Article Synopsis

  • Researchers synthesized and isolated naphthalenediimide-based zwitterionic radicals to enhance electron donor capability, overcoming previous reactivity challenges.
  • The resulting radicals achieved a SOMO level of up to -4.04 eV, allowing for direct reduction of the NDI in its ground state.
  • This method of using a π-electron donor for NDI reduction is novel, as it has typically relied on inorganic, organometallic reagents, or light-driven methods.

Article 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.

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http://dx.doi.org/10.1021/acs.orglett.0c01263DOI Listing

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