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Controlled, Sunlight‐Driven Reversible Cycloaddition of Multiple Singlet Oxygen Molecules to Anthracene‐Containing Trianglimine Macrocycles
Authors:
- Jakub Marcin Grajewski,
- Mikołaj Zgorzelak,
- Agnieszka Magdalena Janiak,
- Katarzyna Małgorzata Taras-Goślińska
- Record ID
- UAM926ffd2a7368438f97c9382037e91568
- Author
- Journal series
- ChemPlusChem, ISSN 2192-6506
- Issue year
- 2022
- Vol
- 87
- No
- 3
- Article number
- e202100510
- ASJC Classification
- Abstract in original language
- Stable macrocyclic organic peroxides: The convenient synthesis of thermally stable chiral macrocyclic peroxides is reported. Macrocycles present thermo stability up to 80 °C. Endoperoxide formation can be promoted by sunlight or by 365 nm UV light irradiation and controlled oxygen release on-demand can be done by the exposure to 275 nm UV light or temperatures above 100 °C. Controlled release of singlet oxygen is of interest not only to chemists, but also to biologists and medics involved in cancer therapy. Two chiral polyaza macrocyclic compounds and their corresponding endoperoxides have been synthesized. These peroxides exhibit high temperature stability, up to 80 °C. Detailed studies on their structure, including X-ray analysis as well as NMR, UV-VIS ECD spectroscopy and theoretical calculations, combined with photochemical measurements indicate that their high stability is related to the arrangement of oxygen atoms in a conformationally stable macrocyclic ring. Despite the change of carbon hybridization from sp2 to sp3 at the 9 and 10 positions of the anthracene units, the macrocyclic skeleton of the obtained compounds does not change its conformation. The obtained endoperoxides can be formed and release singlet oxygen by irradiation with UV light of 365 and 275 nm, respectively. Release of the oxygen does not degrade the macrocyclic structure.
- DOI
- DOI:10.1002/cplu.202100510 Opening in a new tab
- URL
- https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cplu.202100510 Opening in a new tab
- Language
- eng (en) English
- Score (nominal)
- 100
- Score source
- journalList
- Score
- = 100.0, 15-05-2022, ArticleFromJournal
- Publication indicators
- = 0; : 2018 = 0.604; : 2019 (2 years) = 2.753 - 2019 (5 years) =2.723
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- Uniform Resource Identifier
- https://researchportal.amu.edu.pl/info/article/UAM926ffd2a7368438f97c9382037e91568/
- URN
urn:amu-prod:UAM926ffd2a7368438f97c9382037e91568
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or PerishOpening in a new tab system.