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Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study

Authorized Users Only
2015
Authors
Markovic, Jelena M.
Trišović, Nemanja
Mutavdžić, Dragosav
Radotić, Ksenija
Juranić, Ivan
Drakulić, Branko
Marinković, Aleksandar D.
Article (Published version)
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Abstract
Seven symmetrical 2,6-distyrylpyridines, phenyl-substituted with hydrogen-bond donors, hydrogenbond acceptors, halogens and hydrophobic moieties were synthesized and their spectroscopic characterization was done. Solvent effects on the absorption and fluorescence spectra were analyzed and quantified using the Kamlet–Taft and Catalán approach. The obtained results were rationalized by comparison of electrostatic potentials of the molecules in the ground and in excited state and by comparison of the frontier molecular orbitals (HOMO and LUMO), derived from quantum-mechanical calculations (HF, DFT, MP2). Analysis of the results revealed an important influence of non-specific (dispersive) interactions on the solvatochromic behavior of the compounds. 1D and 2D NMR data, in silico obtained conformational assembly of the compound, and the NMR analysis of molecular flexibility in solution (NAMFIS), were used to estimate population of conformers and to deconvolute the UV-Vis spectrum o...f representative derivative; inferring that the conformational assembly is more complex than was assumed in so far published literature data for this class of compounds. Along with this, the emission spectra of the representative compounds were decomposed by the Multivariate Curve Resolution analysis.

Keywords:
UV–Vis spectroscopy / Fluorescence spectroscopy / Conformational preferences
Source:
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2015, 135, 435-446
Publisher:
  • Amsterdam : Elsevier
Funding / projects:
  • Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)
  • Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
  • Study of structure-function relationships in the plant cell wall and modifications of the wall structure by enzyme engineering (RS-173017)
  • Studying climate change and its influence on environment: impacts, adaptation and mitigation (RS-43007)
  • Modeling and Numerical Simulations of Complex Many-Body Systems (RS-171017)
  • High-Performance Computing Infrastructure for South East Europe's Research Communities (EU-261499)
  • European Grid Initiative: Integrated Sustainable Pan-European Infrastructure for Researchers in Europe (EU-261323)
  • PRACE - Third Implementation Phase Project (EU-312763)
Note:
  • Supplementary material: http://dx.doi.org/10.1016/j.saa.2014.07.023

DOI: 10.1016/j.saa.2014.07.023

ISSN: 13861425

PubMed: 25108111

WoS: 000343337700055

Scopus: 2-s2.0-84907364550
[ Google Scholar ]
6
6
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/3431
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Markovic, Jelena M.
AU  - Trišović, Nemanja
AU  - Mutavdžić, Dragosav
AU  - Radotić, Ksenija
AU  - Juranić, Ivan
AU  - Drakulić, Branko
AU  - Marinković, Aleksandar D.
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3431
AB  - Seven symmetrical 2,6-distyrylpyridines, phenyl-substituted with hydrogen-bond donors, hydrogenbond
acceptors, halogens and hydrophobic moieties were synthesized and their spectroscopic characterization
was done. Solvent effects on the absorption and fluorescence spectra were analyzed and quantified
using the Kamlet–Taft and Catalán approach. The obtained results were rationalized by comparison of
electrostatic potentials of the molecules in the ground and in excited state and by comparison of the frontier
molecular orbitals (HOMO and LUMO), derived from quantum-mechanical calculations (HF, DFT,
MP2). Analysis of the results revealed an important influence of non-specific (dispersive) interactions
on the solvatochromic behavior of the compounds. 1D and 2D NMR data, in silico obtained conformational
assembly of the compound, and the NMR analysis of molecular flexibility in solution (NAMFIS), were used
to estimate population of conformers and to deconvolute the UV-Vis spectrum of representative derivative;
inferring that the conformational assembly is more complex than was assumed in so far published
literature data for this class of compounds. Along with this, the emission spectra of the representative
compounds were decomposed by the Multivariate Curve Resolution analysis.
PB  - Amsterdam : Elsevier
T2  - Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy
T1  - Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study
VL  - 135
SP  - 435
EP  - 446
DO  - 10.1016/j.saa.2014.07.023
ER  - 
@article{
author = "Markovic, Jelena M. and Trišović, Nemanja and Mutavdžić, Dragosav and Radotić, Ksenija and Juranić, Ivan and Drakulić, Branko and Marinković, Aleksandar D.",
year = "2015",
abstract = "Seven symmetrical 2,6-distyrylpyridines, phenyl-substituted with hydrogen-bond donors, hydrogenbond
acceptors, halogens and hydrophobic moieties were synthesized and their spectroscopic characterization
was done. Solvent effects on the absorption and fluorescence spectra were analyzed and quantified
using the Kamlet–Taft and Catalán approach. The obtained results were rationalized by comparison of
electrostatic potentials of the molecules in the ground and in excited state and by comparison of the frontier
molecular orbitals (HOMO and LUMO), derived from quantum-mechanical calculations (HF, DFT,
MP2). Analysis of the results revealed an important influence of non-specific (dispersive) interactions
on the solvatochromic behavior of the compounds. 1D and 2D NMR data, in silico obtained conformational
assembly of the compound, and the NMR analysis of molecular flexibility in solution (NAMFIS), were used
to estimate population of conformers and to deconvolute the UV-Vis spectrum of representative derivative;
inferring that the conformational assembly is more complex than was assumed in so far published
literature data for this class of compounds. Along with this, the emission spectra of the representative
compounds were decomposed by the Multivariate Curve Resolution analysis.",
publisher = "Amsterdam : Elsevier",
journal = "Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy",
title = "Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study",
volume = "135",
pages = "435-446",
doi = "10.1016/j.saa.2014.07.023"
}
Markovic, J. M., Trišović, N., Mutavdžić, D., Radotić, K., Juranić, I., Drakulić, B.,& Marinković, A. D.. (2015). Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study. in Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy
Amsterdam : Elsevier., 135, 435-446.
https://doi.org/10.1016/j.saa.2014.07.023
Markovic JM, Trišović N, Mutavdžić D, Radotić K, Juranić I, Drakulić B, Marinković AD. Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study. in Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2015;135:435-446.
doi:10.1016/j.saa.2014.07.023 .
Markovic, Jelena M., Trišović, Nemanja, Mutavdžić, Dragosav, Radotić, Ksenija, Juranić, Ivan, Drakulić, Branko, Marinković, Aleksandar D., "Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study" in Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 135 (2015):435-446,
https://doi.org/10.1016/j.saa.2014.07.023 . .

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