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Solvent and substituent effect on intramolecular charge transfer in 5-arylidene-3-substituted-2,4-thiazolidinediones: Experimental and theoretical study

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2016
303.pdf (3.241Mb)
Authors
Rančić, Milica
Stojiljković, Ivana N.
Milošević, Milena D.
Prlainović, Nevena Z.
Jovanović, Maja
Milčić, Miloš K.
Marinković, Aleksandar
Article (Published version)
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Abstract
The substituent and solvent effect on intramolecular charge transfer (ICT) in 5-arylidene-3-methyl-2,4-thiazolidinediones (series 1) and 5-arylidene-3-phenyl-2,4-thiazolidinediones (series 2) was studied by using experimental and theoretical methodology. The effect of specific and non-specific solvent-solute interactions on the UV-vis absorption maxima shifts was evaluated by using the Kamlet-Taft and Catalán solvent parameter sets. Linear free energy relationships (LFERs) have been applied to the UV-vis and 13C NMR data by using SSP (single substituent parameter) and DSP (dual substituent parameters). Comparative LFER analysis of 10 styrenic series was performed in order to distinguish contribution of structural and electronic substituent effect on extent of π-polarization in a side chain (vinyl) group. Furthermore, the experimental findings were interpreted with the aid of ab initio MP2 and time-dependent density functional (TD-DFT) methods. TD-DFT calculations are performed to quant...ify the efficiency of intramolecular charge transfer (ICT) allowing us to define the charge-transfer distance (DCT), amount of transferred charge (QCT), and difference of dipole moments between the ground and excited states (μCT). It was found that both substituents and solvents influence electron density shift, i.e. extent of conjugation, and affect intramolecular charge transfer character in the course of excitation. © 2016 The Authors.

Keywords:
LFER / LSER / Quantum chemical calculation / Solvatochromism / Substituent effect
Source:
Arabian Journal of Chemistry, 2016
Funding / projects:
  • Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)
Note:
  • Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3613

DOI: 10.1016/j.arabjc.2016.12.013

ISSN: 1878-5352

WoS: 000504900300310

Scopus: 2-s2.0-85009209267
[ Google Scholar ]
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URI
https://cherry.chem.bg.ac.rs/handle/123456789/305
Collections
  • Publikacije
Institution/Community
Hemijski fakultet
TY  - JOUR
AU  - Rančić, Milica
AU  - Stojiljković, Ivana N.
AU  - Milošević, Milena D.
AU  - Prlainović, Nevena Z.
AU  - Jovanović, Maja
AU  - Milčić, Miloš K.
AU  - Marinković, Aleksandar
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/305
AB  - The substituent and solvent effect on intramolecular charge transfer (ICT) in 5-arylidene-3-methyl-2,4-thiazolidinediones (series 1) and 5-arylidene-3-phenyl-2,4-thiazolidinediones (series 2) was studied by using experimental and theoretical methodology. The effect of specific and non-specific solvent-solute interactions on the UV-vis absorption maxima shifts was evaluated by using the Kamlet-Taft and Catalán solvent parameter sets. Linear free energy relationships (LFERs) have been applied to the UV-vis and 13C NMR data by using SSP (single substituent parameter) and DSP (dual substituent parameters). Comparative LFER analysis of 10 styrenic series was performed in order to distinguish contribution of structural and electronic substituent effect on extent of π-polarization in a side chain (vinyl) group. Furthermore, the experimental findings were interpreted with the aid of ab initio MP2 and time-dependent density functional (TD-DFT) methods. TD-DFT calculations are performed to quantify the efficiency of intramolecular charge transfer (ICT) allowing us to define the charge-transfer distance (DCT), amount of transferred charge (QCT), and difference of dipole moments between the ground and excited states (μCT). It was found that both substituents and solvents influence electron density shift, i.e. extent of conjugation, and affect intramolecular charge transfer character in the course of excitation. © 2016 The Authors.
T2  - Arabian Journal of Chemistry
T1  - Solvent and substituent effect on intramolecular charge transfer in 5-arylidene-3-substituted-2,4-thiazolidinediones: Experimental and theoretical study
DO  - 10.1016/j.arabjc.2016.12.013
UR  - Kon_1269
ER  - 
@article{
author = "Rančić, Milica and Stojiljković, Ivana N. and Milošević, Milena D. and Prlainović, Nevena Z. and Jovanović, Maja and Milčić, Miloš K. and Marinković, Aleksandar",
year = "2016",
abstract = "The substituent and solvent effect on intramolecular charge transfer (ICT) in 5-arylidene-3-methyl-2,4-thiazolidinediones (series 1) and 5-arylidene-3-phenyl-2,4-thiazolidinediones (series 2) was studied by using experimental and theoretical methodology. The effect of specific and non-specific solvent-solute interactions on the UV-vis absorption maxima shifts was evaluated by using the Kamlet-Taft and Catalán solvent parameter sets. Linear free energy relationships (LFERs) have been applied to the UV-vis and 13C NMR data by using SSP (single substituent parameter) and DSP (dual substituent parameters). Comparative LFER analysis of 10 styrenic series was performed in order to distinguish contribution of structural and electronic substituent effect on extent of π-polarization in a side chain (vinyl) group. Furthermore, the experimental findings were interpreted with the aid of ab initio MP2 and time-dependent density functional (TD-DFT) methods. TD-DFT calculations are performed to quantify the efficiency of intramolecular charge transfer (ICT) allowing us to define the charge-transfer distance (DCT), amount of transferred charge (QCT), and difference of dipole moments between the ground and excited states (μCT). It was found that both substituents and solvents influence electron density shift, i.e. extent of conjugation, and affect intramolecular charge transfer character in the course of excitation. © 2016 The Authors.",
journal = "Arabian Journal of Chemistry",
title = "Solvent and substituent effect on intramolecular charge transfer in 5-arylidene-3-substituted-2,4-thiazolidinediones: Experimental and theoretical study",
doi = "10.1016/j.arabjc.2016.12.013",
url = "Kon_1269"
}
Rančić, M., Stojiljković, I. N., Milošević, M. D., Prlainović, N. Z., Jovanović, M., Milčić, M. K.,& Marinković, A.. (2016). Solvent and substituent effect on intramolecular charge transfer in 5-arylidene-3-substituted-2,4-thiazolidinediones: Experimental and theoretical study. in Arabian Journal of Chemistry.
https://doi.org/10.1016/j.arabjc.2016.12.013
Kon_1269
Rančić M, Stojiljković IN, Milošević MD, Prlainović NZ, Jovanović M, Milčić MK, Marinković A. Solvent and substituent effect on intramolecular charge transfer in 5-arylidene-3-substituted-2,4-thiazolidinediones: Experimental and theoretical study. in Arabian Journal of Chemistry. 2016;.
doi:10.1016/j.arabjc.2016.12.013
Kon_1269 .
Rančić, Milica, Stojiljković, Ivana N., Milošević, Milena D., Prlainović, Nevena Z., Jovanović, Maja, Milčić, Miloš K., Marinković, Aleksandar, "Solvent and substituent effect on intramolecular charge transfer in 5-arylidene-3-substituted-2,4-thiazolidinediones: Experimental and theoretical study" in Arabian Journal of Chemistry (2016),
https://doi.org/10.1016/j.arabjc.2016.12.013 .,
Kon_1269 .

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