Specific solvent effect on the photophysical behavior of substituted chromones: A combined fluorescence, DFT and MD study
| Autor: | Prayasee Baruah, Semen O. Yesylevskyy, Mostofa Ataur Rohman, Sivaprasad Mitra |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
010304 chemical physics
Hydrogen bond Solvatochromism General Physics and Astronomy 010402 general chemistry 01 natural sciences Fluorescence spectroscopy 0104 chemical sciences Solvent chemistry.chemical_compound Molecular dynamics chemistry Computational chemistry 0103 physical sciences Chromone Density functional theory Physical and Theoretical Chemistry Solvent effects |
| Zdroj: | Chemical Physics. 517:67-79 |
| ISSN: | 0301-0104 |
| Popis: | Solvent dependent photophysical properties of two chromone derivatives, namely 7-amino-2-methyl chromone (AMC) and 3-cyano chromone (CyC), were studied by time-resolved fluorescence spectroscopy, density functional theory (DFT) calculation and molecular dynamics (MD) simulation. Contributions from different solvatochromic parameters were quantitatively estimated using Lippert-Mataga relation, uni-parametric ET(30) and multi-parametric Kamlet–Taft and/or Catalan relations. Notable solvatochromic shift in emission peak was estimated for CyC (Δλ = 130 nm) in comparison with AMC (Δλ = 53 nm). While both solvent hydrogen bond donation acidity and acceptance basicity is important in AMC photophysics, the latter is insignificant for CyC. Estimation of hydrogen bonding pattern in hydrated structures of AMC and CyC derived from MD simulation reveals that specific hydrogen bond donation of the solvent to carbonyl oxygen of the chromones is the most important microstructure modulating the spectral behavior in both the cases, augmenting the experimental observation as well as DFT results. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect