Engineering stable radicals using photochromic triggers

Xuanying Chen, Wandong Zhao, Gleb Baryshnikov, Michael L. Steigerwald, Jian Gu, Yunyun Zhou, Hans Ågren, Qi Zou (), Wenbo Chen () and Liangliang Zhu ()
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Xuanying Chen: Fudan University
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
Wenbo Chen: Shanghai University of Electric Power
Liangliang Zhu: Fudan University

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: 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.

Date: 2020
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DOI: 10.1038/s41467-020-14798-9

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