title: Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study.
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 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.
authors.affiliation: Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11000 Belgrade, Serbia.
authors.forename: Jelena M
authors.initials: JM
authors.lastname: Marković
authors.affiliation: Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11000 Belgrade, Serbia. Electronic address: ntrisovic@tmf.bg.ac.rs.
authors.forename: Nemanja P
authors.initials: NP
authors.lastname: Trišović
authors.affiliation: Institute for Multidisciplinary Research, University of Belgrade, Kneza Višeslava 1, 11000 Beograd, Serbia.
authors.forename: Dragosav
authors.initials: D
authors.lastname: Mutavdžić
authors.affiliation: Institute for Multidisciplinary Research, University of Belgrade, Kneza Višeslava 1, 11000 Beograd, Serbia.
authors.forename: Ksenija
authors.initials: K
authors.lastname: Radotić
authors.affiliation: Department of Chemistry, Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Njegoševa 12, 11000 Belgrade, Serbia.
authors.forename: Ivan O
authors.initials: IO
authors.lastname: Juranić
authors.affiliation: Department of Chemistry, Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Njegoševa 12, 11000 Belgrade, Serbia.
authors.forename: Branko J
authors.initials: BJ
authors.lastname: Drakulić
authors.affiliation: Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11000 Belgrade, Serbia.
authors.forename: Aleksandar D
authors.initials: AD
authors.lastname: Marinković
mesh_terms: D065966:Absorption, Physicochemical; D002725:Chloroform / Q000737:chemistry; D004583:Electrons; D008958:Models, Molecular; D008968:Molecular Conformation; D015999:Multivariate Analysis; D066244:Proton Magnetic Resonance Spectroscopy; D011725:Pyridines / Q000737:chemistry*; D012044:Regression Analysis; D012997:Solvents / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D055672:Static Electricity; D013816:Thermodynamics
chemical_list: C528388:2,6 distyrylpyridine; D011725:Pyridines; D012997:Solvents; D002725:Chloroform
keywords: Conformational preferences; Fluorescence spectroscopy; UV–Vis spectroscopy