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Controlled, Sunlight‐Driven Reversible Cycloaddition of Multiple Singlet Oxygen Molecules to Anthracene‐Containing Trianglimine Macrocycles

Controlled, Sunlight‐Driven Reversible Cycloaddition of Multiple Singlet Oxygen Molecules to... 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png ChemPlusChem Wiley

Controlled, Sunlight‐Driven Reversible Cycloaddition of Multiple Singlet Oxygen Molecules to Anthracene‐Containing Trianglimine Macrocycles

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Publisher
Wiley
Copyright
© 2022 Wiley‐VCH GmbH
eISSN
2192-6506
DOI
10.1002/cplu.202100510
Publisher site
See Article on Publisher Site

Abstract

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.

Journal

ChemPlusChemWiley

Published: Mar 1, 2022

Keywords: anthracene; endoperoxides; macrocycles; singlet oxygen; trianglimines

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