1. Novel Metal-Free Synthesis of 3-Substituted Isocoumarins and Evaluation of Their Fluorescence Properties for Potential Applications.
- Author
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Sun, Mei, Zeng, Chong-Yang, Bu, Lu-Lu, Xu, Mai, Chen, Kai, Liu, Jia-Lin, Zhang, Tao, Dai, Jia-You, Hong, Jia-Xin, and Ding, Ming-Wu
- Subjects
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FLUORESCENCE yield , *FLUORESCENCE , *ISOCOUMARINS , *WITTIG reaction , *STOKES shift , *COUMARINS - Abstract
A novel metal-free synthesis of 3-substituted isocoumarins through a sequential O-acylation/Wittig reaction has been established. The readily accessible (2-carboxybenzyl)-triphenylphosphonium bromide and diverse chlorides produced various 1H-isochromen-1-one in the presence of triethylamine, employing sequential O-acylation and an intramolecular Wittig reaction of acid anhydride. Reactions using these facile conditions have exhibited high functional group tolerance and excellent yields (up to 90%). Moreover, the fluorescence properties of isocoumarin derivatives were evaluated at the theoretical and experimental levels to determine their potential application in fluorescent materials. These derivatives have good photoluminescence in THF with a large Stokes shift and an absolute fluorescence quantum yield of up to 14%. [ABSTRACT FROM AUTHOR]
- Published
- 2024
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