Novel Metal-Free Synthesis of 3-Substituted Isocoumarins and Evaluation of Their Fluorescence Properties for Potential Applications
Mei Sun,
Chong-Yang Zeng,
Lu-Lu Bu,
Mai Xu,
Kai Chen,
Jia-Lin Liu,
Tao Zhang,
Jia-You Dai,
Jia-Xin Hong,
Ming-Wu Ding
Affiliations
Mei Sun
School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China
Chong-Yang Zeng
School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China
Lu-Lu Bu
School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China
Mai Xu
School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China
Kai Chen
School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China
Jia-Lin Liu
School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China
Tao Zhang
School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China
Jia-You Dai
School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China
Jia-Xin Hong
College of Food Science and Engineering, Jiangxi Agricultural University, Nanchang 330045, China
Ming-Wu Ding
Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, Central China Normal University, Wuhan 430079, China
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%.
