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

来源：

CHEMPHYSCHEM | 2024年 / 25卷 / 21期

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

页数：7

共 35 条

[1]

[Anonymous], INVESTIGATION OF FREE-RADICALS AND CATION-RADICALS OF PHENOXAZINE, PHENOTHIAZINE, AND PHENOTHIAZINE-DERIVATIVES BY ELECTRON-PARAMAGNETIC-RES AND ELECTRON-NUCLEAR RESONANCE, BULLETIN

[2] Novel phenoxazine-benzonitrile and phenothiazine-benzonitrile donor-acceptor molecules with thermally activated delayed fluorescence (TADF) [J].

Baraket, Faiza ;

Pedras, Bruno ;

Torres, Erica ;

Brites, Maria Joao ;

Dammak, Mohamed ;

Berberan-Santos, Mario N. .

DYES AND PIGMENTS, 2020, 175

[3] Analysis of actinomycin D-DNA model complexes using a quantum-chemical criterion: Mulliken overlap populations [J].

Bendic, C ;

Enache, M ;

Volanschi, E .

JOURNAL OF MOLECULAR GRAPHICS & MODELLING, 2005, 24 (01) :10-16

[4] Antitumor agents.: 1.: Synthesis, biological evaluation, and molecular modeling of 5H-pyrido[3,2-a]phenoxazin-5-one, a compound with potent antiproliferative activity [J].

Bolognese, A ;

Correale, G ;

Manfra, M ;

Lavecchia, A ;

Mazzoni, O ;

Novellino, E ;

Barone, V ;

Pani, A ;

Tramontano, E ;

La Colla, P ;

Murgioni, C ;

Serra, I ;

Setzu, G ;

Loddo, R .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (24) :5205-5216

[5] Outer-sphere electron transfer from carbazoles to halomethanes. Reduction potentials of halomethanes measured by fluorescence quenching experiments [J].

Bonesi, SM ;

Erra-Balsells, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2000, (07) :1583-1595

[6] Optically Triggered Planarization of Boryl-Substituted Phenoxazine: Another Horizon of TADF Molecules and High-Performance OLEDs [J].

Chen, Deng-Gao ;

Lin, Tzu-Chieh ;

Chen, Chi-Lin ;

Chen, Yi-Ting ;

Chen, Yi-An ;

Lee, Gene-Hsiang ;

Chou, Pi-Tai ;

Liao, Chia-Wei ;

Chiu, Po-Chen ;

Chang, Chih-Hao ;

Lien, Yi-Jyun ;

Chi, Yun .

ACS APPLIED MATERIALS & INTERFACES, 2018, 10 (15) :12886-12896

[7] Looped out and perpendicular: Deformation of Watson-Crick base pair associated with actinomycin D binding [J].

Chou, SH ;

Chin, KH ;

Chen, FM .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (10) :6625-6630

[8]

Cibi R., 2016, Int. J. Curr. Microbiol. Appl. Sci, V5, P405

[9] HETEROCYCLIC FREE-RADICALS .6. SUBSTITUENT EFFECTS ON DISTRIBUTION OF SPIN-DENSITY IN 10-ARYLPHENOXAZINE AND 10-ARYLPHENOTHIAZINE CATION RADICALS [J].

CLARKE, D ;

GILBERT, BC ;

HANSON, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1976, (01) :114-124

[10] The photocatalytic decomposition of chloroform by tetrachloroaurate(III) [J].

Cohen, Larissa R. ;

Pena, Laura A. ;

Seidl, Anton J. ;

Olsen, Janet M. ;

Wekselbaum, Jennifer ;

Hoggard, Patrick E. .

MONATSHEFTE FUR CHEMIE, 2009, 140 (10) :1159-1165

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