Kinetic Stabilization of Carbazole Nitroxides by Inclusion in a Macrocage and Their Electron Spin Resonance Characterization

Hikaru Hashimoto, Yusuke Inagaki, Hiroyuki Momma, Eunsang Kwon, Wataru Setaka

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Some nitroxides, for example, tetramethylpyridiniumoxide, are known as stable radicals; however, carbazole nitroxide is less stable. The kinetic stabilization of labile radicals by introduction of bulky substituents is usually effective to investigate intrinsic properties of the molecule because of small electronic perturbation induced by the substituents. In this study, macrocage molecules with a carbazole nitroxide connected by covalent bonds were newly designed as kinetically stabilized carbazole nitroxides. The nitroxides were prepared and characterized by electron spin resonance spectroscopy. The caged nitroxides presented long half-lives (∼50 h) by kinetic analysis.

Original languageEnglish
Pages (from-to)11783-11789
Number of pages7
JournalJournal of Organic Chemistry
Volume84
Issue number18
DOIs
Publication statusPublished - 2019 Sep 20

ASJC Scopus subject areas

  • Organic Chemistry

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