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New Singlet Oxygen Donors Based on Naphthalenes: Synthesis, Physical Chemical Data, and Improved Stability

  • Singlet oxygen donors are of current interest for medical applications, but suffer from a short half-life leading to low singlet oxygen yields and problems with storage. We have synthesized more than 25new singlet oxygen donors based on differently substituted naphthalenes in only a few steps. The influence of functional groups on the reaction rate of the photooxygenations, thermolysis, half-life, and singlet oxygen yield has been thoroughly studied. We determined various thermodynamic data and compared them with density functional calculations. Interestingly, remarkable stabilities of functional groups during the photooxygenations and stabilizing effects for some endoperoxides during the thermolysis have been found. Furthermore, we give evidence for a partly concerted and partly stepwise thermolysis mechanism leading to singlet and triplet oxygen, respectively. Our results might be interesting for dark oxygenations and future applications in medicine.

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Metadaten
Author:Matthias Klaper, Torsten LinkerORCiDGND
DOI:https://doi.org/10.1002/chem.201500146
ISSN:0947-6539 (print)
ISSN:1521-3765 (online)
Pubmed Id:http://www.ncbi.nlm.nih.gov/pubmed?term=25919359
Parent Title (English):Chemistry - a European journal
Publisher:Wiley-VCH
Place of publication:Weinheim
Document Type:Article
Language:English
Year of first Publication:2015
Year of Completion:2015
Release Date:2017/03/27
Tag:density functional calculations; oxygenation; peroxides; photodynamic therapy; singlet oxygen
Volume:21
Issue:23
Pagenumber:9
First Page:8569
Last Page:8577
Funder:University of Potsdam
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert