TY  - JOUR
A1  - Fudickar, Werner
A1  - Linker, Torsten
T1  - Release of Singlet Oxygen from Organic Peroxides under Mild Conditions
JF  - ChemPhotoChem
N2  - Singlet oxygen can be released in the dark in nearly quantitative yield from endoperoxides of naphthalenes, anthracenes and pyridones as an alternative to its generation by photosensitization. Recently, new donor systems have been designed which operate at very low temperatures but which are prepared from their parent forms at acceptable rates. Enhancement of the reactivity of donors is conveniently achieved by the design of the substitution pattern or through the use of plasmonic heating of nanoparticle-bound donors. The most important aim of these donor molecules is to transfer singlet oxygen in a controlled and directed manner to a target. Low temperatures and the linking between donors and acceptors reduce the random walk of oxygen and may force an attack at the desired position. By using chiral donor systems, new stereocenters might be introduced into prochiral acceptors.
KW  - donor-acceptor systems
KW  - oxygenation
KW  - peroxides
KW  - polycycles
KW  - retro reactions
Y1  - 2018
U6  - https://doi.org/10.1002/cptc.201700235
SN  - 2367-0932
VL  - 2
IS  - 7
SP  - 548
EP  - 558
PB  - Wiley-VCH
CY  - Weinheim
ER  - 
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  -