Optically Active Neutral Spiro‐Fused Mixed‐Valence Radicals: Synthesis and Characterization

Synthesis of the novel stable mixed‐valence aminylborate radicals in the form of the individual enantiomers is reported. The mixed‐valence gives rise to such important properties of the radicals as strong “panchromatic” absorption in UV–vis–NIR range, ambipolar redox behavior (facile formation of the oppositely charged states), the SOMO/HOMO inversion (the promising feature for the spintronics), and weak fluorescent properties, which are discussed and rationalized using the DFT calculations. Molecular architecture of the novel radicals based on the multipoint binding between two halves of the molecule makes them configurationally stable and intrinsically chiral, and that is the important benefit. Notably, the reported examples of optically active radical luminophores are still rare. Optically active neutral mixed‐valence organic radicals have not been reported so far.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2026-10-28
DOI
https://doi.org/10.1002/ejoc.70930
Primary Topic
Organoboron and organosilicon chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Optically Active Neutral Spiro‐Fused Mixed‐Valence Radicals: Synthesis and Characterization

Sergey Gennadievich Dorofeev, D. A. Davydov, Oleg A. Levitskiy, Elena Vadimovna Kudryashova et al.
2 links
European Journal of Organic Chemistry
Organoboron and organosilicon chemistry
article

Optically Active Neutral Spiro‐Fused Mixed‐Valence Radicals: Synthesis and Characterization

Sergey Gennadievich Dorofeev, D. A. Davydov, Oleg A. Levitskiy, Elena Vadimovna Kudryashova, Tatiana V. Magdesieva
article en

Abstract

Synthesis of the novel stable mixed‐valence aminylborate radicals in the form of the individual enantiomers is reported. The mixed‐valence gives rise to such important properties of the radicals as strong “panchromatic” absorption in UV–vis–NIR range, ambipolar redox behavior (facile formation of the oppositely charged states), the SOMO/HOMO inversion (the promising feature for the spintronics), and weak fluorescent properties, which are discussed and rationalized using the DFT calculations. Molecular architecture of the novel radicals based on the multipoint binding between two halves of the molecule makes them configurationally stable and intrinsically chiral, and that is the important benefit. Notably, the reported examples of optically active radical luminophores are still rare. Optically active neutral mixed‐valence organic radicals have not been reported so far.

European Journal of Organic Chemistry
Lomonosov Moscow State University (RU)
Russian Science Foundation, Lomonosov Moscow State University
Openalex Percentile: Top 26%
Organoboron and organosilicon chemistry
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