Release of Singlet Oxygen from Aromatic Endoperoxides by Chemical Triggers
- The generation of reactive singlet oxygen under mild conditions is of current interest in chemistry, biology, and medicine. We were able to release oxygen from dipyridylanthracene endoperoxides (EPOs) by using a simple chemical trigger at low temperature. Protonation and methylation of such EPOs strongly accelerated these reactions. Furthermore, the methyl pyridinium derivatives are water soluble and therefore serve as oxygen carriers in aqueous media. Methylation of the EPO of the ortho isomer affords the parent form directly without increasing the temperature under very mild conditions. This exceptional behavior is ascribed to the close contact between the nitrogen atom and the peroxo group. Singlet oxygen is released upon this reaction, and can be used to oxygenate an acceptor such as tetramethylethylene in the dark with no heating. Thus, a new chemical source of singlet oxygen has been found, which is triggered by a simple stimulus.
Author details: | Werner FudickarORCiDGND, Torsten LinkerORCiDGND |
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DOI: | https://doi.org/10.1002/anie.201806881 |
ISSN: | 1433-7851 |
ISSN: | 1521-3773 |
Pubmed ID: | https://pubmed.ncbi.nlm.nih.gov/30070421 |
Title of parent work (English): | Angewandte Chemie : a journal of the Gesellschaft Deutscher Chemiker ; International edition |
Publisher: | Wiley-VCH |
Place of publishing: | Weinheim |
Publication type: | Article |
Language: | English |
Date of first publication: | 2018/08/02 |
Publication year: | 2018 |
Release date: | 2021/09/24 |
Tag: | anthracenes; donor-acceptor systems; mild reaction conditions; selective oxidations; singlet oxygen |
Volume: | 57 |
Issue: | 39 |
Number of pages: | 5 |
First page: | 12971 |
Last Page: | 12975 |
Funding institution: | University of Potsdam |
Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
DDC classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Peer review: | Referiert |