Spectroscopic and theoretical studies of dual fluorescence in 2-hydroxy-n-(2-phenylethyl)benzamide induced by ESIPT process – Solvent effects
Authors:
- Agnieszka Niemczynowicz,
- Grzegorz Czernel,
- Arkadiusz Matwijczuk,
- Marcin Makowski,
- Katarzyna Pustuła,
- Dariusz Karcz,
- Alicja Matwijczuk,
- Andrzej Górecki,
- Agnieszka I. Piotrowicz-Cieślak
Abstract
This work discusses the theoretical ([TD]DFT) and spectroscopic investigation into2-Hydroxy-N-(2-phenylethyl)benzamide(SAL3)and its physiochemical behaviour in the selected organic solvents. The compound demon-strated a dualfluorescence effect in alcoholic solutions (methanol, ethanol, isopropanol), while in acetonitrile(ACN), dimethylsulfoxide (DMSO) and non-polar solvents (n-Hexane,n-Heptane, chloroform) only a singleemission maximum was observed. The noticeable shortening of averagefluorescence lifetime, the employed detailed analysis of solvatochromic shifts of absorption spectra in the function of polarizability related to achange 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.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.
- Record ID
- CUTa9d34627a0c64688b23ef9369082413a
- Publication categories
- ;
- Author
- Journal series
- Journal of Luminescence, ISSN 0022-2313, e-ISSN 1872-7883
- Issue year
- 2019
- Vol
- 208
- Pages
- 125-134
- Other elements of collation
- schem.; tab.; wykr.; Bibliografia (na s.) - 133-134; Bibliografia (liczba pozycji) - 72; Oznaczenie streszczenia - Abstr.; Numeracja w czasopiśmie - Vol. 208
- Keywords in English
- dual fluorescence effect, molecular spectroscopy, salicylic acid derivatives, [TD] DFT calculations, H-bonds
- DOI
- DOI:10.1016/j.jlumin.2018.12.024 Opening in a new tab
- URL
- https://www.sciencedirect.com/science/article/pii/S0022231318314959 Opening in a new tab
- Language
- eng (en) English
- Score (nominal)
- 100
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUTa9d34627a0c64688b23ef9369082413a/
- URN
urn:pkr-prod:CUTa9d34627a0c64688b23ef9369082413a
* presented citation count is obtained through Internet information analysis, and it is close to the number calculated by the Publish or PerishOpening in a new tab system.