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Int. J. Mol. Sci. 2014, 15(10), 18706-18724; doi:10.3390/ijms151018706

Synthesis, X-ray Structure, Spectroscopic Properties and DFT Studies of a Novel Schiff Base

Department of Chemical Engineering, Feng Chia University, Taichung 40724, Taiwan
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Received: 1 August 2014 / Revised: 23 September 2014 / Accepted: 9 October 2014 / Published: 17 October 2014
(This article belongs to the Section Physical Chemistry, Theoretical and Computational Chemistry)
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Abstract

A series of Schiff bases, salicylideneaniline derivatives 14, was synthesized under mild conditions and characterized by 1H NMR, HRMS, UV-Vis and fluorescence spectra, and single-crystal X-ray diffraction. In solid and aprotic solvents 14 exist mainly as E conformers that possess an intramolecular six-membered-ring hydrogen bond. A weak intramolecular C–H×××F hydrogen bond is also observed in fluoro-functionalized Schiff base 4, which generates another S(6) ring motif. The C–H×××F hydrogen bond further stabilizes its structure and leads it to form a planar configuration. Compounds 13 exhibit solely a long-wavelength proton-transfer tautomer emission, while dipole-functionalized Schiff base 4 shows remarkable dual emission originated from the excited-state intramolecular charge transfer (ESICT) and excited-state intramolecular proton transfer (ESIPT) states. Furthermore, the geometric structures, frontier molecular orbitals (MOs) and the potential energy curves for 14 in the ground and the first singlet excited state were fully rationalized by density functional theory (DFT) and time-dependent DFT calculations. View Full-Text
Keywords: salicylideneaniline derivatives; Schiff bases; ESICT; ESIPT; solvatochromism; Lippert-Mataga equation; Schaefer’s correlation; density functional theory calculations salicylideneaniline derivatives; Schiff bases; ESICT; ESIPT; solvatochromism; Lippert-Mataga equation; Schaefer’s correlation; density functional theory calculations
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Chen, K.-Y.; Tsai, H.-Y. Synthesis, X-ray Structure, Spectroscopic Properties and DFT Studies of a Novel Schiff Base. Int. J. Mol. Sci. 2014, 15, 18706-18724.

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