Spectroscopic and theoretical studies of dual fluorescence in 2-hydroxy-n-(2-phenylethyl)benzamide induced by esipt process. Solvents effects
Authors:
- A. Niemczynowicz,
- G. Czarnel,
- A. Matwijczuk,
- M. Makowski,
- K. Pustuła,
- D. Karcz,
- A. Matwijczuk,
- A. Górecki,
- A. I. Piotrowicz-Cieślak,
- E. Chruściel
Abstract
In this work we discusses the theoretical ([TD]DFT) and molecular spectroscopic investigation of 2-Hydroxy-N-(2-phenylethyl)benzamide (SAL3). We also discuss its physiochemical behaviour in the selected organic solvents (polar and non-polar). The compound demonstrated a very interesting dual fluorescence effect in alcoholic solutions (e.g.: methanol, ethanol or isopropanol), while in acetonitrile (ACN), dimethylsulfoxide (DMSO) and nonpolar solvents (like: n-Hexane, n-Heptane, chloroform) only a single emission maximum was observed. The noticeable shortening of average fluorescence lifetime (TCSPC), the employed detailed analysis of solvatochromic shifts of absorption spectra in the function of polarizability related to a change in the induction polarization of the environment and, above all, the performed quantum-mechanical calculations [TD]DFT with a detailed analysis of excited states, clearly indicate a connection between the observed fluorescence effects and processes related to changes in the system’s structure in the excited state. We also noticed that the observed fluorescence effects (dual fluorescence) are quenched by aggregation effects of this compounds. Based on these experimental and theoretical studies, it has been proposed that the environment (solvent) polarity-induced dual fluorescence effect in SAL3 is related to the Excited-State Intramolecular Proton Transfer (ESIPT) process. Also, the quantum-mechanic studies [TD] DFT point to the specific conformation of SAL3 molecule characteristic of dual fluorescence emission. The results of spectroscopic studies on a selected compounds from SAL3 in a micellar and liposomal systems will be presented.
- Record ID
- CUTbd1cde4d1b4b4d8eaa4072af71866463
- Publication categories
- ; ;
- Author
- Journal series
- European Biophysics Journal With Biophysics Letters, ISSN 0175-7571, e-ISSN 1432-1017
- Issue year
- 2019
- Vol
- 48
- Pages
- 213
- Article number
- P-543
- Other elements of collation
- Numeracja w czasopiśmie - Vol. 48, Suppl. 1
- Substantive notes
- DOI: 10.1007/s00249-019-01373-4 (całość)
- Conference
- JOINT 12th EBSA congress and 10th ICBP – IUPAP congress (12th EBSA, 10th ICBP – IUPAP), 2019, 20-06-2019 - 24-06-2019, Madrid, Hiszpania
- Keywords in English
- dual fluorescence, ESPIT Processes, solvent effects, benzamide
- URL
- https://link.springer.com/article/10.1007/s00249-019-01373-4 Opening in a new tab
- Language
- eng (en) English
- Score (nominal)
- 0
- Additional fields
- Indeksowana w: Web of Science
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUTbd1cde4d1b4b4d8eaa4072af71866463/
- URN
urn:pkr-prod:CUTbd1cde4d1b4b4d8eaa4072af71866463
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