Abstract
We report the synthesis and characterization, colorimetric anion sensors properties, density functional theory (DFT) calculation studies of a Schiff base (E)-2-[(3,5-bis(trifluoromethyl)phenylimino)methyl]-4-chlorophenol. The molecular structure of the title compound was experimentally determined using X-ray single-crystal data and was compared to the structure predicted by theoretical calculations using DFT. The experimental and calculated data (using DFT) of the title compound have been compared. To investigate the tautomeric stability, some properties such as total energy, HOMO and LUMO energies, the chemical hardness (η), the ionization potential, the electron affinity, the absolute electronegativity (χ), the absolute softness (σ) of the compound were obtained at B3LYP/6–311++G(d,p) level in the gas phase and solvent phase. The calculated results showed that the enol-imine form of the compound was more favorite than keto-amine form. The colorimetric response of the Schiff base receptors in DMSO was investigated.
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The authors are grateful to the Scientific and Technical Research Council of Turkey (TÜBİTAK) for the financial support of this work, grant number TÜBİTAK 115F253.
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Figure S1
. Comparison of the experimental and calculated FT-IR spectra of the investigated compounds: (a) Observed spectra; (b) Theoretical spectra at B3LYP/6-311++G(d,p) level. (TIF 663 KB)
Figure S2
. Correlation graphics of unscaled (calculated) and experimental frequencies of the title compound. (TIF 494 KB)
Figure S3
. The energy difference between the gas phase and solvent media and dipole moment for different solvent media. (TIF 492 KB)
Figure S4
. Molecular electrostatic potential (MEP) map calculated at B3LYP/6-311++G(d,p) level. (TIF 952 KB)
Figure S5
. UV-visible spectrum of the compound in DMSO solvent. (TIF 759 KB)
Figure S6
. Molecular orbital surfaces and energy levels for the HOMO, HOMO-1, LUMO, and LUMO+1 of the title compound computed at B3LYP/6-311++G(d,p) level (TIF 683 KB)
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Ünver, H., Zeyrek, C.T., Boyacioglu, B. et al. Synthesis, Crystal Structure, Anion Sensing Applications and DFT Studies of (E)-2-[(3,5-Bis(trifluoromethyl)phenylimino)methyl]-4-chlorophenol. J Chem Crystallogr 49, 232–244 (2019). https://doi.org/10.1007/s10870-018-0758-7
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DOI: https://doi.org/10.1007/s10870-018-0758-7