TY  - JOUR
A1  - Klaper, Matthias
A1  - Linker, Torsten
T1  - New Singlet Oxygen Donors Based on Naphthalenes: Synthesis, Physical Chemical Data, and Improved Stability
JF  - Chemistry - a European journal
N2  - 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.
KW  - density functional calculations
KW  - oxygenation
KW  - peroxides
KW  - photodynamic therapy
KW  - singlet oxygen
Y1  - 2015
U6  - https://doi.org/10.1002/chem.201500146
SN  - 0947-6539
SN  - 1521-3765
VL  - 21
IS  - 23
SP  - 8569
EP  - 8577
PB  - Wiley-VCH
CY  - Weinheim
ER  -