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Effect of the spacer length and nitroxide sterical shielding upon photostability of spin-labeled kynurenines
- Source :
- Journal of Photochemistry and Photobiology A: Chemistry. :76-84
- Publication Year :
- 2016
- Publisher :
- Elsevier BV, 2016.
-
Abstract
- The synthesis of the natural molecular UV filters − kynurenines (KN) − covalently bound to nitroxides has recently been proposed as an alternative for traditional combination of antioxidants and UV-filters in sunscreen formulations. Due to the spin-exchange interaction between KN and nitroxide moieties, the triplet lifetimes in such conjugates are much shorter than in KN molecule, but the triplet quantum yields are significantly higher. The reaction of intramolecular electron transfer between photoexcited KN and nitroxide moieties is the main factor determining the quantum yield of KN-RNO conjugates photodecomposition. Searching for a method to suppress this side process we synthesized analogues of previously prepared conjugates with the enlarged spacer between the nitroxide and kynurenine parts and with the sterically hindered access to the nitroxide group. The new spin-labeled kynurenines showed at least three-fold higher photostability compared to the previously synthesized compounds of this type.
- Subjects :
- Steric effects
Nitroxide mediated radical polymerization
010405 organic chemistry
Chemistry
General Chemical Engineering
Photodissociation
General Physics and Astronomy
Quantum yield
General Chemistry
010402 general chemistry
Photochemistry
01 natural sciences
0104 chemical sciences
Electron transfer
Covalent bond
Intramolecular force
Molecule
Subjects
Details
- ISSN :
- 10106030
- Database :
- OpenAIRE
- Journal :
- Journal of Photochemistry and Photobiology A: Chemistry
- Accession number :
- edsair.doi...........4fed9a7fc262a18021ad75a85ecc1d3e