Photostability of Phenoxazine Derivatives

被引:0
作者
Goll, Felix D. [1 ]
Welscher, Philipp J. [1 ]
Bodenmueller, Franz [1 ]
Blinder, Remi [2 ]
Jelezko, Fedor [2 ]
Ziener, Ulrich [1 ]
机构
[1] Ulm Univ, Inst Organ Chem Macromol Chem & Organ Mat 3, D-89081 Ulm, Germany
[2] Ulm Univ, Inst Quantum Opt, D-89081 Ulm, Germany
关键词
Heterocycles; Phenoxazine; Photochemistry; Photolysis; Radicals; PHENOTHIAZINE; DECOMPOSITION;
D O I
10.1002/cphc.202400506
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Phenoxazine is a commonly used molecular building block, for example in optoelectronic applications and pharmaceuticals. However, it is highly susceptible to rapid photodegradation, especially in halogenated solvents. In the present study, we identify the degradation products in both halogenated and non-halogenated solvents by UV/Vis absorption, NMR spectroscopy and mass spectrometry. We also propose a substitution strategy aimed at effectively suppressing the high photoreactivity. Kinetic studies show that the quantum yield of photodegradation phi differs by a factor of more than 1000 between trisubstituted derivatives and N-substituted phenoxazine.
引用
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页数:7
相关论文
共 35 条
[11]   Non-Tertiary Alkyl Substituents Enhance High-Temperature Radical Trapping by Phenothiazine and Phenoxazine Antioxidants [J].
Farmer, Luke A. ;
Pratt, Derek A. .
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (09) :6126-6137
[12]   Phenoxazine: A Privileged Scaffold for Radical-Trapping Antioxidants [J].
Farmer, Luke A. ;
Haidasz, Evan A. ;
Griesser, Markus ;
Pratt, Derek A. .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (19) :10523-10536
[13]  
Frisch M. J., 2016, GAUSSIAN 16 REV C01
[14]   PHOTOCHEMISTRY OF PHENOXAZINE - A FLASH-PHOTOLYTIC STUDY [J].
GEGIOU, D ;
HUBER, JR ;
WEISS, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (17) :5058-&
[15]   FREE-RADICAL STUDIES BY RESONANCE RAMAN-SPECTROSCOPY - PHENOTHIAZINE, 10-METHYLPHENOTHIAZINE, AND PHENOXAZINE RADICAL CATIONS [J].
HESTER, RE ;
WILLIAMS, KPJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1981, (05) :852-859
[16]   Electrochemical and Electrochromic Properties of Polymers Based on 2,5-di(2-thienyl)-1H-pyrrole and Different Phenothiazine Units [J].
Hu, Bin ;
Li, Chun-yang ;
Chu, Jun-wei ;
Liu, Zeng-chen ;
Zhang, Xin-lei ;
Jin, Lin .
JOURNAL OF THE ELECTROCHEMICAL SOCIETY, 2019, 166 (02) :H1-H11
[17]   Green multi-resonance thermally activated delayed fluorescence emitters containing phenoxazine units with highly efficient electroluminescence [J].
Hu, Jia-Jun ;
Luo, Xu-Feng ;
Zhang, Yi-Pin ;
Mao, Meng-Xi ;
Ni, Hua-Xiu ;
Liang, Xiao ;
Zheng, You-Xuan .
JOURNAL OF MATERIALS CHEMISTRY C, 2022, 10 (02) :768-773
[18]  
Koopmans T., 1934, Physica, V1, P104, DOI DOI 10.1016/S0031-8914(34)90011-2
[19]   Bond dissociation energies of the N-H bond and rate constants for the reaction with alkyl, alkoxyl, and peroxyl radicals of phenothiazines and related compounds [J].
Lucarini, M ;
Pedrielli, P ;
Pedulli, GF ;
Valgimigli, L ;
Gigmes, D ;
Tordo, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (49) :11546-11553
[20]   PHENOXAZINE .2. SYNTHESE, KONSTITUTION UND LICHTABSORPTION VON BIPHENOXAZINEN UND PHENOXAZYL-PHENOXAZONEN [J].
MUSSO, H .
CHEMISCHE BERICHTE-RECUEIL, 1959, 92 (11) :2873-2881