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A Mesoionic Platform for Persistent Anionic Nitrogen-Centered Radicals
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DOI：10.1002/anie.3083427.png)
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Abstract
En 中文
Persistent anionic N-centered radicals are exceptionally rare, as the coexistence of negative charge and unpaired electron density typically promotes protonation, aggregation, and irreversible redox chemistry. Here we introduce mesoionic 1,2,3-triazines as a platform for stabilizing such elusive open-shell anions. These compounds undergo clean and reversible one-electron reduction to generate negatively charged nitrogen-centered radicals, and suitable substitution enables their isolation as crystalline salts. EPR spectroscopy, single-crystal x-ray diffraction, and computational analysis reveal dominant nitrogen spin localization together with reduction-induced structural changes consistent with occupation of a parent triazine antibonding orbital. The resulting anionic radicals display chemically clean electron-transfer behavior and are reversibly oxidized to their zwitterionic precursors. These findings further highlight the potential of mesoionic 1,2,3-triazines as redox-active molecular platforms for applications in complex electrochemical environments.
Keywords:
mesoionic heterocycles
nitrogen radicals
persistent radical anions
redox-active molecules
single-electron transfer
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