Bis-Spiro-Oxetane and Bis-Spiro-Tetrahydrofuran Pyrroline Nitroxide Radicals: Synthesis and Electron Spin Relaxation Studies

Shengdian Huang, Maren Pink, Thacien Ngendahimana, Suchada Rajca, Gareth R. Eaton, Sandra S. Eaton, Andrzej Rajca

Research output: Contribution to journalArticlepeer-review

Abstract

Synthesis of bis-spiro-oxetane and bis-spiro-tetrahydrofuran pyrroline nitroxide radicals relies on the Mitsunobu reaction-mediated double cyclizations of N-Boc protected pyrroline tetraols. Structures of the nitroxide radicals are supported by X-ray crystallography. In a trehalose/sucrose matrix at room temperature, the bis-spiro-oxetane nitroxide radical possesses electron spin coherence time, Tm ≈ 0.7 μs. The observed enhanced Tm is most likely associated with strong hydrogen bonding of oxetane moieties to the trehalose/sucrose matrix.

Original languageEnglish (US)
Pages (from-to)13636-13643
Number of pages8
JournalJournal of Organic Chemistry
Volume86
Issue number19
DOIs
StatePublished - Oct 1 2021

ASJC Scopus subject areas

  • Organic Chemistry

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