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- Title
Synthesis, X-ray Structure, Spectroscopic Properties and DFT Studies of a Novel Schiff Base.
- Authors
Kew-Yu Chen; Tsai, Hsing-Yang
- Abstract
A series of Schiffbases, salicylideneaniline derivatives 1-4, 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 1-4 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 1-3 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 1-4 in the ground and the first singlet excited state were fully rationalized by density functional theory (DFT) and time-dependent DFT calculations.
- Subjects
ANILINE synthesis; SCHIFF bases; X-ray diffraction; DENSITY functional theory; HYDROGEN bonding; EXCITED state chemistry
- Publication
International Journal of Molecular Sciences, 2014, Vol 15, Issue 10, p18706
- ISSN
1661-6596
- Publication type
Article
- DOI
10.3390/ijms151018706