Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study
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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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Show full item recordAbstract
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 preferencesSource:
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2015, 135, 435-446Publisher:
- Amsterdam : Elsevier
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