Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study
Samo za registrovane korisnike
2015
Autori
Marković, Jelena M.Trisović, Nemanja
Mutavdžić, Dragosav
Radotić, Ksenija
Juranic, Ivan O.
Drakulic, Branko J.
Marinković, Aleksandar
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Ključne reči:
UV-Vis spectroscopy / Fluorescence spectroscopy / Conformational preferencesIzvor:
Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 2015, 135, 435-446Izdavač:
- Pergamon-Elsevier Science Ltd, Oxford
Finansiranje / projekti:
- High-Performance Computing Infrastructure for South East Europe's Research Communities (EU-261499)
- Modeliranje i numeričke simulacije složenih višečestičnih sistema (RS-171017)
- Racionalni dizajn i sinteza biološki aktivnih i koordinacionih jedinjenja i funkcionalnih materijala, relevantnih u (bio)nanotehnologiji (RS-172035)
- Ispitivanja odnosa struktura-funkcija u ćelijskom zidu biljaka i izmene strukture zida enzimskim inženjeringom (RS-173017)
DOI: 10.1016/j.saa.2014.07.023
ISSN: 1386-1425
PubMed: 25108111
WoS: 000343337700055
Scopus: 2-s2.0-84907364550
Institucija/grupa
Institut za multidisciplinarna istraživanjaTY - JOUR AU - Marković, Jelena M. AU - Trisović, Nemanja AU - Mutavdžić, Dragosav AU - Radotić, Ksenija AU - Juranic, Ivan O. AU - Drakulic, Branko J. AU - Marinković, Aleksandar PY - 2015 UR - http://rimsi.imsi.bg.ac.rs/handle/123456789/885 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 Trisović, Nemanja and Mutavdžić, Dragosav and Radotić, Ksenija and Juranic, Ivan O. and Drakulic, Branko J. 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., Trisović, N., Mutavdžić, D., Radotić, K., Juranic, I. O., Drakulic, B. J.,& 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, Trisović N, Mutavdžić D, Radotić K, Juranic IO, Drakulic BJ, 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., Trisović, Nemanja, Mutavdžić, Dragosav, Radotić, Ksenija, Juranic, Ivan O., Drakulic, Branko J., 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 . .