Hydrogen bond capability tunable different 'relay-race' mechanisms of the excited-state proton transfer process for 4′-methoxy-3-hydroxyflavone
| Autor: | Cai Jixing, G. Y. Jin, Hui Li, Chao Xin, Zhi Wei, Boshi Yuan |
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| Rok vydání: | 2020 |
| Předmět: |
Proton
Hydrogen bond 3-Hydroxyflavone Intermolecular force 02 engineering and technology General Chemistry 010402 general chemistry 021001 nanoscience & nanotechnology Condensed Matter Physics Photochemistry 01 natural sciences 0104 chemical sciences Electronic Optical and Magnetic Materials Biomaterials chemistry.chemical_compound chemistry Excited state Intramolecular force Materials Chemistry Dimethylformamide Density functional theory Electrical and Electronic Engineering 0210 nano-technology |
| Zdroj: | Organic Electronics. 81:105678 |
| ISSN: | 1566-1199 |
| DOI: | 10.1016/j.orgel.2020.105678 |
| Popis: | The different “relay-race” mechanisms of proton transfer process are investigated for 4′-methoxy-3-hydroxyflavone (MHF) in methanol (MeOH) and dimethylformamide (DMF) characterized by different hydrogen bond (HB) capabilities. Based on the density functional theory and time-dependent density functional theory, we demonstrate that the asynchronous excited-state intermolecular double proton transfer via two intermolecular HBs happens for MHF in MeOH. Differently, in DMF solvent, it breaks the intramolecular HB and forms a single intermolecular HB. And the intermolecular single proton transfer occurs in DMF upon photoexcitation. The excited-state intermolecular HBs both in MHF-MeOH and MHF-DMF complex are proved to be significantly strengthened, which facilitate the proton transfer process. Importantly, it reveals that the higher electrostatic potential and the stronger proton capture ability of DMF than MeOH induce a faster proton transfer for MHF-DMF in experiment. The results highlight the significance of the solvent HB capability in effecting the proton transfer mechanism, and hence have potential to design and develop excellent fluorescent probes. |
| Databáze: | OpenAIRE |
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