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The complex photochemistry of coumarin-3-carboxylic acid in acetonitrile and methanol

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Abstract

Irradiation of coumarin-3-carboxylic acid in acetonitrile and methanol solutions at 355 nm results in complex multistep photochemical transformations, strongly dependent on the solvent properties and oxygen content. A number of reaction intermediates, which themselves undergo further (photo)chemical reactions, were identified by steady-state and transient absorption spectroscopy, mass spectrometry, and NMR and product analyses. The triplet excited compound in acetonitrile undergoes decarboxylation to give a 3-coumarinyl radical that traps molecular oxygen to form 3-hydroxycoumarin as the major but chemically reactive intermediate. This compound is oxygenated by singlet oxygen, produced by coumarin-3-carboxylic acid sensitization, followed by a pyrone ring-opening reaction to give an oxalic acid derivative. The subsequent steps lead to the production of salicylaldehyde, carbon monoxide, and carbon dioxide as the final products. When 3-coumarinyl radical is not trapped by oxygen in degassed acetonitrile, it abstracts hydrogen from the solvent and undergoes triplet-sensitized [2 + 2] cycloaddition. The reaction of 3-coumarinyl radical with oxygen is largely suppressed in aerated methanol as a better H-atom donor, and coumarin is obtained as the primary product in good yields. Because coumarin derivatives are used in many photophysical and photochemical applications, this work provides detailed and sometimes surprising insights into their complex phototransformations.

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Acknowledgements

Support for this work was provided by the Czech Science Foundation (GA21-01799S). We thank the RECETOX Research Infrastructure (No. LM2018121) financed by the Ministry of Education, Youth and Sports, and the Operational Programme Research, Development and Education (the CETOCOEN EXCELLENCE project No. CZ.02.1.01/0.0/0.0/17_043/0009632) for supportive background. This project was also supported by the European Union’s Horizon 2020 Research and Innovation Programme under grant agreement No. 857560. This publication reflects only the authors' view, and the European Commission is not responsible for any use that may be made of the information it contains. We thank Luboš Jílek and Marek Martínek for their help with experiments and use of the instrumentation, Chitose Youhei for his help with transient spectroscopy experiments, and Miroslava Bittová (all Masaryk University) for HRMS analyses.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, Brno, Czech Republic

    Qiuyun Yang & Petr Klán

  2. RECETOX, Faculty of Science, Masaryk University, Kamenice 5, Brno, Czech Republic

    Qiuyun Yang & Petr Klán

  3. Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice, Czech Republic

    Jiří Váňa

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  1. Qiuyun Yang
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  2. Jiří Váňa
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Correspondence to Petr Klán.

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Dedicated to Prof. Jakob Wirz on the occasion of his 80th birthday.

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Yang, Q., Váňa, J. & Klán, P. The complex photochemistry of coumarin-3-carboxylic acid in acetonitrile and methanol. Photochem Photobiol Sci 21, 1481–1495 (2022). https://doi.org/10.1007/s43630-022-00238-8

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  • DOI: https://doi.org/10.1007/s43630-022-00238-8

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