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Eosin Y Catalyzed Photochemical Synthesis of Arylated Phenothiazones.
- Source :
-
ACS omega [ACS Omega] 2024 Aug 11; Vol. 9 (33), pp. 35458-35462. Date of Electronic Publication: 2024 Aug 11 (Print Publication: 2024). - Publication Year :
- 2024
-
Abstract
- In the presence of Eosin Y ( EY ), the synthesis of substituted phenothiazones was carried out efficiently using various substituted 2-aminothiophenol, diazonium salts, and 1,4-napthaquinones ( 1,4-NQ ) at room temperature (RT) (condition: green LED of 525 nm, 44 W; reaction time: 8 h, isolated yield: 68-90%). A fluorescence quenching experiment and density functional theory (DFT) calculations suggested that the triplet photoexcited state of EY (EY*; τT = 320 ± 10 ns) converts to EY <superscript>+•</superscript> via oxidative quenching by ArN <subscript>2</subscript> <superscript>+</superscript> (-1.11 V vs SCE for EY* to EY <superscript>+•</superscript> ) initially. Thiyl and aryl radicals were captured as TEMPO adducts in high-resolution mass spectroscopy (HRMS). The reaction was not inhibited by the addition of a singlet oxygen quencher such as 1,4-diazobicyclo [2.2.2] octane (DABCO), which suggests that singlet oxygen is not participated.<br />Competing Interests: The authors declare no competing financial interest.<br /> (© 2024 The Authors. Published by American Chemical Society.)
Details
- Language :
- English
- ISSN :
- 2470-1343
- Volume :
- 9
- Issue :
- 33
- Database :
- MEDLINE
- Journal :
- ACS omega
- Publication Type :
- Academic Journal
- Accession number :
- 39184487
- Full Text :
- https://doi.org/10.1021/acsomega.4c02167