An unprecedented photochemical reaction for anthracene-containing derivatives

Zhao, Jiang-Lin; Jiang, Xue-Kai; Wu, Chong; Wang, Chuan-Zeng; Zeng, Xi; Redshaw, Carl; Yamato, Takehiko

Abstract

A series of anthracene-containing derivatives have been synthesised and characterised. The photochemical behaviour of these derivatives have been investigated by 1 H NMR spectroscopy. An unprecedented photolysis reaction for anthracene-containing derivatives was observed in the case of anthracenes directly armed with a -CH 2 O-R group upon UV irradiation. The photolysis reaction process has been demonstrated to occur in three steps. Firstly, the anthracene-containing derivatives are converted into the corresponding endoperoxide intermediate upon UV irradiation in the presence of air; then, the endoperoxide intermediate is decomposed to the corresponding starting compound and 9-anthraldehyde; finally, 9-anthraldehyde is further oxidised to anthraquinone. Additionally, the photolysis reaction of anthracene-containing derivatives is significantly promoted in the presence of a thiacalix[4]arene platform.

Citation

Zhao, J.-L., Jiang, X.-K., Wu, C., Wang, C.-Z., Zeng, X., Redshaw, C., & Yamato, T. (2016). An unprecedented photochemical reaction for anthracene-containing derivatives. Chemphyschem, 17(20), 3217-3222. https://doi.org/10.1002/cphc.201600783

• Journal Article Type: Article
• Acceptance Date: Jul 20, 2016
• Online Publication Date: Sep 5, 2016
• Publication Date: Oct 18, 2016
• Deposit Date: Aug 23, 2016
• Publicly Available Date: Sep 5, 2016
• Journal: Chemphyschem
• Print ISSN: 1439-7641
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 17
• Issue: 20
• Pages: 3217-3222
• DOI: https://doi.org/10.1002/cphc.201600783
• Keywords: Anthracene, Thiacalix[4]arene, Photolysis, Decomposition
• Public URL: https://hull-repository.worktribe.com/output/442433
• Publisher URL: http://onlinelibrary.wiley.com/doi/10.1002/cphc.201600783/abstract?
• Additional Information: Authors' accepted manuscript of article published in: Chemphyschem, 2016, v.17, issue 20
• Contract Date: Aug 23, 2016