One pot synthesis, X-ray crystal structure of 2-(2′-hydroxyphenyl)oxazolo[4,5-b]pyridine derivatives and studies of their optical properties
| Autor: | Rafael Arcos-Ramos, Rosa Angeles Vázquez-García, Norberto Farfán, Luis Humberto Mendoza-Huizar, Lizbeth Juárez-Guerra, Susana Rojas-Lima, Horacio Briseño-Ortega, Rosa Santillan, Heralio López-Ruiz |
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| Rok vydání: | 2018 |
| Předmět: |
010405 organic chemistry
Organic Chemistry One-pot synthesis Crystal structure Time-dependent density functional theory 010402 general chemistry Ring (chemistry) 01 natural sciences Medicinal chemistry 0104 chemical sciences Analytical Chemistry Inorganic Chemistry chemistry.chemical_compound chemistry Pyridine Moiety Cyclic voltammetry Phenylboronic acid Spectroscopy |
| Zdroj: | Journal of Molecular Structure. 1157:119-126 |
| ISSN: | 0022-2860 |
| Popis: | A series of five 2-(2-hydroxyphenyl)oxazolo [4,5-b]pyridines (HPOP) (3a-e), where four are novel, were synthesized by a mild, one pot, phenylboronic acid-NaCN catalyzed reaction. Spectroscopic characterization and photophysical properties of these compounds are reported. Absorption and excitation spectra of the compounds were dependent on the substituents in the phenyl ring. Fluorescence quantum yields (0.009–0.538) were associated with the donor strength and the position of the substituents. Also, DFT analysis allowed us to determine the contribution of diethylamino and methoxy moieties to the π-system, which is in agreement with the experimental data analyzed in solution and by cyclic voltammetry. The results obtained in the solid state by single-crystal X-ray diffraction experiments indicate that, the quasi-planarity envisioned for the explored compounds is present, supporting the hypothesis that both the H-bonding of a hydroxyl group to the C N moiety and a donor groups such as diethylamino and methoxy moieties favor an electronic communication. Due to the facile synthesis and their photophysical properties, the novel HPOP 3a-e have potential application as organic semiconductors. |
| Databáze: | OpenAIRE |
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