Solvent and substituent effect on intramolecular charge transfer in 5-arylidene-3-substituted-2,4-thiazolidinediones: Experimental and theoretical study
2019
Autori
Rančić, MilicaStojiljković, Ivana
Milošević, Milena D.
Prlainović, Nevena
Jovanović, Maja
Milčić, Miloš
Marinković, Aleksandar
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
The substituent and solvent effect on intramolecular charge transfer (ICT) in 5-aryli dene-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 Catalan solvent parameter sets. Linear free energy relationships (LFERs) have been applied to the UV-vis and C-13 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 p-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 qua...ntify 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 (mu CT). 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.
Ključne reči:
Solvatochromism / Substituent effect / LFER / LSER / Quantum chemical calculationIzvor:
Arabian Journal of Chemistry, 2019, 12, 8, 5142-5161Izdavač:
- Elsevier, Amsterdam
Finansiranje / projekti:
- Proučavanje sinteze, strukture i aktivnosti organskih jedinjenja prirodnog i sintetskog porekla (RS-MESTD-Basic Research (BR or ON)-172013)
DOI: 10.1016/j.arabjc.2016.12.013
ISSN: 1878-5352
WoS: 000504900300310
Scopus: 2-s2.0-85009209267
Institucija/grupa
Tehnološko-metalurški fakultetTY - JOUR AU - Rančić, Milica AU - Stojiljković, Ivana AU - Milošević, Milena D. AU - Prlainović, Nevena AU - Jovanović, Maja AU - Milčić, Miloš AU - Marinković, Aleksandar PY - 2019 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4139 AB - The substituent and solvent effect on intramolecular charge transfer (ICT) in 5-aryli dene-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 Catalan solvent parameter sets. Linear free energy relationships (LFERs) have been applied to the UV-vis and C-13 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 p-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 (mu CT). 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. PB - Elsevier, Amsterdam 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 EP - 5161 IS - 8 SP - 5142 VL - 12 DO - 10.1016/j.arabjc.2016.12.013 ER -
@article{ author = "Rančić, Milica and Stojiljković, Ivana and Milošević, Milena D. and Prlainović, Nevena and Jovanović, Maja and Milčić, Miloš and Marinković, Aleksandar", year = "2019", abstract = "The substituent and solvent effect on intramolecular charge transfer (ICT) in 5-aryli dene-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 Catalan solvent parameter sets. Linear free energy relationships (LFERs) have been applied to the UV-vis and C-13 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 p-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 (mu CT). 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.", publisher = "Elsevier, Amsterdam", 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", pages = "5161-5142", number = "8", volume = "12", doi = "10.1016/j.arabjc.2016.12.013" }
Rančić, M., Stojiljković, I., Milošević, M. D., Prlainović, N., Jovanović, M., Milčić, M.,& Marinković, A.. (2019). 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 Elsevier, Amsterdam., 12(8), 5142-5161. https://doi.org/10.1016/j.arabjc.2016.12.013
Rančić M, Stojiljković I, Milošević MD, Prlainović N, Jovanović M, Milčić M, 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. 2019;12(8):5142-5161. doi:10.1016/j.arabjc.2016.12.013 .
Rančić, Milica, Stojiljković, Ivana, Milošević, Milena D., Prlainović, Nevena, Jovanović, Maja, Milčić, Miloš, 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, 12, no. 8 (2019):5142-5161, https://doi.org/10.1016/j.arabjc.2016.12.013 . .