Abstract
1-Phenyl-3-(4-nitrophenyl)-5-(2-thienyl)-2-pyrazoline was synthesized and characterized by elemental analysis, IR and X-ray single crystal diffraction. UV-Vis spectra and fluorescence spectra were measured. Density functional theory calculations on the structure of the title compound were performed at the B3LYP/6-311G** level of theory. NPA atomic charge distributions indicate that, although the S atom in the thienyl ring loses coordination capacity, the title compound still may be used as a potential multi-dentate ligand to coordinate with metallic ions. The calculation of the second order optical nonlinearity was carried out. Natural bond orbital analyses indicate that the electronic absorption bands are mainly derived from the contribution of n → π* and π → π* transitions. Fluorescence spectra determination shows that the title compound is a potential orange-light emitting material.
Highlights
Pyrazoline derivatives are five-membered, nitrogen-containing heterocyclic compounds with high hole-transport efficiency, excellent blue emission and high quantum yield [1,2,3], which have made them useful as fluorescent brightening agents, fluorescence chemosensors, hole-transport materials in Molecules 2014, 19 electrophotography, OLED and as fluorescent materials [4,5,6,7,8]
All of the bond lengths and bond angles in the phenyl rings are in the normal range
The geometry of the solid-state structures is subject to intermolecular forces, such as van der Waals interactions and crystal packing forces, which make most of the experimental bond lengths shorter than the theoretical ones; (2) in the solid state, there exists a C–H···π supramolecular interaction corresponding with the thienyl ring, while in theoretical calculations, supramolecular interactions are neglected, which, to some extent, may lead to bigger bond length and bond angle differences between the experiments and calculations corresponding to the thienyl ring
Summary
Pyrazoline derivatives are five-membered, nitrogen-containing heterocyclic compounds with high hole-transport efficiency, excellent blue emission and high quantum yield [1,2,3], which have made them useful as fluorescent brightening agents, fluorescence chemosensors, hole-transport materials in Molecules 2014, 19 electrophotography, OLED and as fluorescent materials [4,5,6,7,8]. The success of DFT is mainly due to the fact that it describes small molecules more reliably than Hartree-Fock theory It is computationally more economic than wave function based methods with inclusion of electron correlation [23,24]. To our knowledge, no structural data obtained either by experimental or theoretical methods have been reported so far for the title compound, 1-phenyl-3-(4-nitrophenyl)-5-(2-thienyl)-2-pyrazoline, which contains both a pyrazolinyl and a substituted thienyl group. After the title compound was synthesized by a refluxing method (see Scheme 1), a concerted approach by X-ray crystallography and DFT calculations was used, which takes advantage of both the high interpretative power of the theoretical studies and the precision and reliability of the experimental method.
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