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

Jyoti Shukla; Sharvan Kumar; Rustam; Pritam Mukhopadhyay

doi:10.1021/acs.orglett.0c01263

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

Org Lett. 2020 Aug 21;22(16):6229-6233. doi: 10.1021/acs.orglett.0c01263. Epub 2020 May 1.

Authors

Jyoti Shukla¹, Sharvan Kumar¹, Rustam¹, Pritam Mukhopadhyay¹

Affiliation

¹ Supramolecular and Material Chemistry Lab, School of Physical Sciences, Jawaharlal Nehru University, New Delhi 110067, India.

PMID: 32356990
DOI: 10.1021/acs.orglett.0c01263

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.