Benzotristhiazole based chromophores for nonlinear optics

► Various methylations of unsymmetrical trimethylbenzotristhiazole were studied. ► The structure of the obtained monomethylated salt was proved by X-ray analysis. ► The X-ray analysis was in accord with the quantum-chemical calculations (DFT-B3LYP). ► A series of condensation products with push–pull...

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Bibliographic Details
Published in:Journal of molecular structure 2012-11, Vol.1027, p.70-80
Main Authors: Fülöpová, Andrea, Magdolen, Peter, Sigmundová, Ivica, Zahradník, Pavol, Rakovský, Erik, Cigáň, Marek
Format: Article
Language:English
Subjects:
Aldehydes
Azolium salts
Benzotristhiazole
Beta
condensation
DFT calculations
energy
Fluorescence
Hyperpolarizability
iodides
Mathematical analysis
Methylation
Molecular structure
optical properties
Orbitals
Quantum chemistry
UV–Vis spectra
X-radiation
X-ray analysis
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Summary:► Various methylations of unsymmetrical trimethylbenzotristhiazole were studied. ► The structure of the obtained monomethylated salt was proved by X-ray analysis. ► The X-ray analysis was in accord with the quantum-chemical calculations (DFT-B3LYP). ► A series of condensation products with push–pull structure was prepared. ► Relations between structure, linear and nonlinear optical properties were examined. Methylation of unsymmetrical trimethylbenzotristhiazole with various reagents has been studied in details. The structure of obtained 2,3,5,8-tetramethylbisthiazolo[4,5-e;5,4-g]-1,3-benzothiazolium iodide has been proved by X-ray analysis in accord with the quantum-chemical calculations at DFT-B3LYP level. The electron-withdrawing tetramethylbenzotristhiazolium building block was submitted to Knoevenagel reaction with aromatic aldehydes containing an electron-releasing group. This led to a series of condensation products with push–pull structure. Relations between structure, linear (UV–Vis and fluorescence spectra) and nonlinear optical properties (calculated frontier orbital energy gap, BLA index, hyperpolarizabilities β and γ) have been investigated.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2012.06.018