Stable Spiro-Fused Diarylaminyl Radicals: A New Type of a Neutral Mixed-Valence System

Vyacheslav V. Sentyurin, Oleg A. Levitskiy, Alexey V. Bogdanov, Tatiana S. Yankova, Sergey G. Dorofeev, Konstantin A. Lyssenko, Victoria E. Gontcharenko, Tatiana V. Magdesieva*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

A new type of neutral mixed-valence system was synthesized using a facile one-pot procedure. The spiro-conjugated framework is additionally “fastened” with a biphenyl bridge, which does not directly participate in spin delocalization but makes the molecule stable and influences the reorganization energy and the energy barrier of the intramolecular electron transfer. The in-depth experimental and quantum-chemical study allowed determining the radicals as the Class II Robin-Day-mixed-valence systems. The structure of the radicals was confirmed by the X-ray data, which are relatively rare for Class II MV molecules. Advanced properties of the radicals, such as an ambipolar redox behavior and panchromatic absorption in the visible and NIR regions, along with their stability, make them of interest for materials science. All radicals demonstrate the SOMO-HOMO inversion phenomenon, which was supported by the DFT and the experimental study.

Original languageEnglish
Article numbere202301250
JournalChemistry - A European Journal
Volume29
Issue number43
DOIs
Publication statusPublished - 1 Aug 2023
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • General Chemistry
  • Organic Chemistry

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