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Photo-Fries reaction in acetoxyphenyl thiophenes
- Source :
- Journal of Photochemistry and Photobiology A: Chemistry. 397:112502
- Publication Year :
- 2020
- Publisher :
- Elsevier BV, 2020.
-
Abstract
- Two new acetoxyphenyl thiophenes with different conjugation length and undergoing the photo-Fries reaction upon exposure to UV light are presented. These molecules have been characterized in solution by means of different spectroscopic techniques in order to study the evolution and selectivity of the photo-induced reaction. During such a reaction, isosbestic points appear in the UV–vis spectra, indicating a good selectivity of the reaction for both the derivatives. By means of IR measurements, we follow the reaction and determine the kinetics and the quantum yield. The photoproducts are isolated by HPLC and characterized by 1H-NMR whose results confirm the formation of the ortho derivative as the most probable one and we estimate the degree of conversion of the reaction. High-level quantum mechanical calculations both in gas and solvated phase are employed to strongly support the interpretation of the experimental results, and assess the reaction product.
- Subjects :
- General Chemical Engineering
Acetoxyphenyl thiophenes
Kinetics
General Physics and Astronomy
Quantum yield
Infrared spectroscopy
02 engineering and technology
DFT calculations
010402 general chemistry
Photochemistry
01 natural sciences
H-NMR spectroscopy
Ultraviolet visible spectroscopy
Phase (matter)
Molecule
Isosbestic point
Chemistry
General Chemistry
021001 nanoscience & nanotechnology
UV–vis spectroscopy
0104 chemical sciences
IR spectroscopy
0210 nano-technology
Selectivity
Photo-Fries reaction
Subjects
Details
- ISSN :
- 10106030
- Volume :
- 397
- Database :
- OpenAIRE
- Journal :
- Journal of Photochemistry and Photobiology A: Chemistry
- Accession number :
- edsair.doi.dedup.....1c11a41ac057f547dc0fc72a8687e088