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An Air-Stable Organic Radical from a Controllable Photoinduced Domino Reaction of a Hexa-aryl Substituted Anthracene

Mao, Xiaoyu; Zhang, Jianyu; Wang, Xiaohui; Zhang, Haoke; Wei, Peifa; Sung, Herman H. Y.; Williams, Ian D.; Feng, Xing; Ni, Xin Long; Redshaw, Carl; Elsegood, Mark R. J.; Lam, Jacky W. Y.; Tang, Ben Zhong

Authors

Xiaoyu Mao

Jianyu Zhang

Xiaohui Wang

Haoke Zhang

Peifa Wei

Herman H. Y. Sung

Ian D. Williams

Xing Feng

Xin Long Ni

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Professor Carl Redshaw C.Redshaw@hull.ac.uk
Professor of Inorganic Materials Chemistry and REF Lead for Chemistry

Mark R. J. Elsegood

Jacky W. Y. Lam

Ben Zhong Tang



Abstract

Air-stable organic radicals and radical ions have attracted great attention for their far-reaching application ranging from bioimaging to organic electronics. However, because of the highly reactive nature of organic radicals, the design and synthesis of air-stable organic radicals still remains a challenge. Herein, an air-stable organic radical from a controllable photoinduced domino reaction of a hexa-aryl substituted anthracene is described. The domino reaction involves a photoinduced [4 + 2] cycloaddition reaction, rearrangement, photolysis, and an elimination reaction; 1H/13C NMR spectroscopy, high resolution mass spectrometry, single-crystal X-ray diffraction, and EPR spectroscopy were exploited for characterization. Furthermore, a photoinduced domino reaction mechanism is proposed according to the experimental and theoretical studies. In addition, the effects of employing push and pull electronic groups on the controllable photoinduced domino reaction were investigated. This article not only offers a new blue emitter and novel air-stable organic radical compound for potential application in organic semiconductor applications, but also provides a perspective for understanding the fundamentals of the reaction mechanism on going from anthracene to semiquinone in such anthracene systems.

Citation

Mao, X., Zhang, J., Wang, X., Zhang, H., Wei, P., Sung, H. H. Y., …Tang, B. Z. (2021). An Air-Stable Organic Radical from a Controllable Photoinduced Domino Reaction of a Hexa-aryl Substituted Anthracene. Journal of Organic Chemistry, https://doi.org/10.1021/acs.joc.1c00233

Journal Article Type Article
Acceptance Date May 10, 2021
Online Publication Date May 25, 2021
Publication Date May 25, 2021
Deposit Date May 26, 2021
Publicly Available Date May 26, 2022
Journal Journal of Organic Chemistry
Print ISSN 0022-3263
Electronic ISSN 1520-6904
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
DOI https://doi.org/10.1021/acs.joc.1c00233
Keywords Hydrocarbons; Organic reactions; Aromatic compounds; Nuclear magnetic resonance spectroscopy; Irradiation
Public URL https://hull-repository.worktribe.com/output/3773952