Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study
Authorized Users Only
2015
Authors
Marković, Jelena M.Trišović, Nemanja
Mutavdžić, Dragosav
Radotić, Ksenija
Juranić, Ivan
Drakulić, Branko
Marinković, Aleksandar
Article (Published version)
Metadata
Show full item recordAbstract
Seven symmetrical 2,6-distyrylpyridines, phenyl-substituted with hydrogen-bond donors, hydrogen-bond 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 Catalan 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 (HE, 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 silica 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 repres...entative 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 preferencesSource:
Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 2015, 135, 435-446Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
Funding / projects:
- High-Performance Computing Infrastructure for South East Europe's Research Communities (EU-FP7-261499)
- Modeling and Numerical Simulations of Complex Many-Body Systems (RS-MESTD-Basic Research (BR or ON)-171017)
- Studying climate change and its influence on environment: impacts, adaptation and mitigation (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-43007)
- Study of structure-function relationships in the plant cell wall and modifications of the wall structure by enzyme engineering (RS-MESTD-Basic Research (BR or ON)-173017)
DOI: 10.1016/j.saa.2014.07.023
ISSN: 1386-1425
PubMed: 25108111
WoS: 000343337700055
Scopus: 2-s2.0-84907364550
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Marković, Jelena M. AU - Trišović, Nemanja AU - Mutavdžić, Dragosav AU - Radotić, Ksenija AU - Juranić, Ivan AU - Drakulić, Branko AU - Marinković, Aleksandar PY - 2015 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3026 AB - Seven symmetrical 2,6-distyrylpyridines, phenyl-substituted with hydrogen-bond donors, hydrogen-bond 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 Catalan 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 (HE, 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 silica 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 - Pergamon-Elsevier Science Ltd, Oxford T2 - Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy T1 - Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study EP - 446 SP - 435 VL - 135 DO - 10.1016/j.saa.2014.07.023 ER -
@article{ author = "Marković, Jelena M. and Trišović, Nemanja and Mutavdžić, Dragosav and Radotić, Ksenija and Juranić, Ivan and Drakulić, Branko and Marinković, Aleksandar", year = "2015", abstract = "Seven symmetrical 2,6-distyrylpyridines, phenyl-substituted with hydrogen-bond donors, hydrogen-bond 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 Catalan 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 (HE, 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 silica 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 = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy", title = "Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study", pages = "446-435", volume = "135", doi = "10.1016/j.saa.2014.07.023" }
Marković, J. M., Trišović, N., Mutavdžić, D., Radotić, K., Juranić, I., Drakulić, B.,& Marinković, A.. (2015). Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy Pergamon-Elsevier Science Ltd, Oxford., 135, 435-446. https://doi.org/10.1016/j.saa.2014.07.023
Marković JM, Trišović N, Mutavdžić D, Radotić K, Juranić I, Drakulić B, Marinković A. 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 .
Marković, Jelena M., Trišović, Nemanja, Mutavdžić, Dragosav, Radotić, Ksenija, Juranić, Ivan, Drakulić, Branko, Marinković, Aleksandar, "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 . .