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Engineering stable radicals using photochromic triggers

Author

Listed:
  • Xuanying Chen

    (Fudan University
    Shanghai University of Electric Power)

  • Wandong Zhao

    (Shanghai University of Electric Power)

  • Gleb Baryshnikov

    (Division of Theoretical Chemistry and Biology, School of Chemistry, Biotechnology and Health, KTH Royal Institute of Technology)

  • Michael L. Steigerwald

    (Columbia University)

  • Jian Gu

    (Fudan University)

  • Yunyun Zhou

    (Fudan University)

  • Hans Ågren

    (Division of Theoretical Chemistry and Biology, School of Chemistry, Biotechnology and Health, KTH Royal Institute of Technology)

  • Qi Zou

    (Shanghai University of Electric Power
    Columbia University)

  • Wenbo Chen

    (Shanghai University of Electric Power)

  • Liangliang Zhu

    (Fudan University)

Abstract

Long-standing radical species have raised noteworthy concerns in organic functional chemistry and materials. However, there remains a substantial challenge to produce long-standing radicals by light, because of the structural dilemmas between photoproduction and stabilization. Herein, we present a pyrrole and chloride assisted photochromic structure to address this issue. In this well-selected system, production and stabilization of a radical species were simultaneously found accompanied by a photochemical process in chloroform. Theoretical study and mechanism construction indicate that the designed π-system provides a superior spin-delocalization effect and a large steric effect, mostly avoiding possible consumptions and making the radical stable for hours even under an oxygen-saturated condition. Moreover, this radical system can be applied for a visualized and quantitative detection towards peroxides, such as 2,2,6,6-tetramethylpiperidine-1-oxyl, hydrogen peroxide, and ozone. As the detection relies on a radical capturing mechanism, a higher sensing rate was achieved compared to traditional redox techniques for peroxide detection.

Suggested Citation

  • Xuanying Chen & Wandong Zhao & Gleb Baryshnikov & Michael L. Steigerwald & Jian Gu & Yunyun Zhou & Hans Ågren & Qi Zou & Wenbo Chen & Liangliang Zhu, 2020. "Engineering stable radicals using photochromic triggers," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
  • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-14798-9
    DOI: 10.1038/s41467-020-14798-9
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