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

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., Williams, I. D., Feng, X., Ni, X. L., Redshaw, C., Elsegood, M. R. J., Lam, J. W. 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