Theoretical investigation on regulating photophysical properties and proton transfer behavior by electronegativity for near-infrared emitting styryl dyes
© 2024. The Author(s), under exclusive licence to European Photochemistry Association, European Society for Photobiology..
Our main focus is to explore the atomic electronegativity-dependent photoinduced behavior of styryl derivatives (HBO, HBS, and HBSe). The results of structural parameter calculation by the DFT method show that the intramolecular hydrogen bonds of normal and tautomer form are strengthened and weakened, respectively, in an excited state (S1), which is conducive to the excited intramolecular proton transfer (ESIPT) process. The enhancement of excited hydrogen bond is beneficial to the ESIPT process from the aspects of infrared vibration frequency (IR), Mulliken's charge analysis, and density gradient reduction (RDG). Additionally, by determining the bond energy with the band critical point (BCP) parameter, we found that the lower the electronegativity of the atom, the larger the hydrogen bond strength at the excited state and the more likely ESIPT reaction occurs. Meanwhile, the intramolecular H-bonds O-H…N in HBO, HBS, and HBSe are enhanced with the weakened electron-withdrawing capacity of the atom (from O to S and Se). Subsequently, frontier molecular orbital (FMOs) and charge density difference (CDD) analyses essentially revealed that electron redistribution induces the ESIPT process. Low atomic electronegativity exhibits the high chemical activity of the excited state. Furthermore, to demonstrate the electronegativity-dependent ESIPT behavior of the system, we built potential energy curves (PECs) and located the transition states (TS) of proton transfer processes.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:23 |
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| Enthalten in: |
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology - 23(2024), 3 vom: 02. März, Seite 575-585 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Liu, Xiu-Min [VerfasserIn] |
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| Links: |
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| Themen: |
Atomic electronegativity |
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| Anmerkungen: |
Date Revised 02.04.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1007/s43630-024-00540-7 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM368762653 |
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| 245 | 1 | 0 | |a Theoretical investigation on regulating photophysical properties and proton transfer behavior by electronegativity for near-infrared emitting styryl dyes |
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| 520 | |a © 2024. The Author(s), under exclusive licence to European Photochemistry Association, European Society for Photobiology. | ||
| 520 | |a Our main focus is to explore the atomic electronegativity-dependent photoinduced behavior of styryl derivatives (HBO, HBS, and HBSe). The results of structural parameter calculation by the DFT method show that the intramolecular hydrogen bonds of normal and tautomer form are strengthened and weakened, respectively, in an excited state (S1), which is conducive to the excited intramolecular proton transfer (ESIPT) process. The enhancement of excited hydrogen bond is beneficial to the ESIPT process from the aspects of infrared vibration frequency (IR), Mulliken's charge analysis, and density gradient reduction (RDG). Additionally, by determining the bond energy with the band critical point (BCP) parameter, we found that the lower the electronegativity of the atom, the larger the hydrogen bond strength at the excited state and the more likely ESIPT reaction occurs. Meanwhile, the intramolecular H-bonds O-H…N in HBO, HBS, and HBSe are enhanced with the weakened electron-withdrawing capacity of the atom (from O to S and Se). Subsequently, frontier molecular orbital (FMOs) and charge density difference (CDD) analyses essentially revealed that electron redistribution induces the ESIPT process. Low atomic electronegativity exhibits the high chemical activity of the excited state. Furthermore, to demonstrate the electronegativity-dependent ESIPT behavior of the system, we built potential energy curves (PECs) and located the transition states (TS) of proton transfer processes | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Atomic electronegativity | |
| 650 | 4 | |a Energy barrier | |
| 650 | 4 | |a Excited state intramolecular proton transfer | |
| 650 | 4 | |a Photophysical properties | |
| 700 | 1 | |a Xia, Qi-Ying |e verfasserin |4 aut | |
| 700 | 1 | |a Ju, Xue-Hai |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology |d 2002 |g 23(2024), 3 vom: 02. März, Seite 575-585 |w (DE-627)NLM124270131 |x 1474-9092 |7 nnns |
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