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This content will become publicly available on June 2, 2026

Title: Persistent free radicals in leaves as a stable standard for quantifying free radicals
Award ID(s):
2142825 1834638
PAR ID:
10647897
Author(s) / Creator(s):
; ;
Publisher / Repository:
Elsevier
Date Published:
Journal Name:
MethodsX
ISSN:
2215-0161
Subject(s) / Keyword(s):
Biogenic persistent free radicals BPFRs Crape myrtle leaves Electron paramagnetic resonance ESR measurements Organic radical quantification DPPH alternative Radical stability Free radical calibration Environmental applications
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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    Abstract A new strategy to stabilize free radicals electronically is described by conjugating formally antiaromatic substituents to the free radical. With an antiaromatic substituent, the radical acts as an electron sink to allow configuration mixing of a low‐energy zwitterionic state that provides antiaromaticity relief to the substituent. A combination of X‐ray crystallography, VT‐EPR and VT‐UV/Vis spectroscopy, as well as computational analysis, was used to investigate this phenomenon. We find that this strategy of antiaromaticity relief is successful at stabilizing radicals, but only if the antiaromatic substituent is constrained to be planar by synthetically imposed conformational restraints that enable state mixing. This work leads to the counterintuitive finding that increasing the antiaromaticity of the radical substituent leads to greater radical stability, providing proof of concept for a new stereoelectronic approach for stabilizing free radicals. 
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