SYNTHESIS, CHARACTERIZATION AND COMPUTATIONAL STUDIES OF SCHIFF BASE.

What is it about?

(E)-2-{[(2-Aminopyridin-3-yl)imino]-methyl}-4,6-di-tert-butyl-phenol ( 3: ), a ligand containing an intramolecular hydrogen bond, was prepared according to a previous literature report, with modifications, and was characterized by UV-vis, FTIR, 1H-NMR, 13C-NMR, HHCOSY, TOCSY and cyclic voltammetry. Computational analyses at the level of DFT and TD-DFT were performed to study its electronic and molecular structures. The results of these analyses elucidated the behaviors of the UV-vis and electrochemical data. Analysis of the transitions in the computed spectrum showed that the most important band is primarily composed of a HOMO→LUMO transition, designated as an intraligand (IL) charge transfer.

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Why is it important?

Schiff base ligands derived from salicylaldehyde containing OH...N type hydrogen bonding have been studied due to the versatility of their electronic and steric properties. Different metal complexes with Schiff base ligands have been synthesized and studied because of their ability to form stable complexes. These complexes have also been used in analytical chemistry for the spectrophotometric determination of heavy metals. Furthermore, they are used as catalysts in chemical and photochemical reactions as well as many other applications. Schiff bases with an -OH group in the ortho position relative to an imino group -C=N- have generated much interest due to the existence of an intramolecular hydrogen bond between the OH and the nitrogen atom. Bio-inspired compounds that contain an intramolecular hydrogen bond have been utilized as dyes in photoelectrochemical cells. A detailed study of such compounds demonstrated that their electrochemical activity is similar to the activity observed for redox processes in biological systems. This research emphasizes the importance of an intramolecular hydrogen bond in such systems, which has been the subject of much investigation. With this in mind, we aimed to investigate the possible use of an aminopyridine, (E)-2-{[(2-aminopyridin-3-yl)imino]-methyl}-4,6-di-tert-butyl-phenol,containing a Schiff base and possessing an intramolecular hydrogen bond as a substituent group. A complete study of its electronic properties was performed to understand the role of the hydrogen bond.