Synthesis, structural characterization, and antibacterial activity of diorganotin complexes of Schiff base derived from 4-(diethylamino)salicylaldehyde and L-tyrosine

Abstract

Four new diorganotin complexes of Schiff base derived from 4-(diethylamino)salicylaldehyde and L-tyrosine, R₂Sn[2-O-4-Et₂NC₆H₃CH=NCH(CH₂C₆H₄OH-4)COO] (R = Me (1), Et (2), Cy (3), Ph (4)), were synthesized by the one-pot reaction of L-tyrosine, 4-(diethylamino)salicylaldehyde and diorganotin dichloride in the presence of triethylamine and characterized by means of elemental analysis, IR, ¹H and ¹³C NMR spectra, and the X-ray single-crystal diffraction. X-Ray analyses of 1–4 revealed that the tin atoms of the complexes exhibit seriously distorted trigonal-bipyramidal geometries with a monodentate carboxylate oxygen atom and a phenolic oxygen atom occupying the axial positions. The intermolecular O─H⋅⋅⋅O hydrogen bonds and Sn⋅⋅⋅O weak interactions connected the molecules into one-dimensional supramolecular chain. Bioassay results indicated that 1–4 had moderate antibacterial activity against Escherichia coli and the fluorescence determinations show the complexes may be explored for potential luminescent materials.

Keywords:

• Organotin
• antibacterial activity
• Schiff base
• fluorescence
• crystal structure

Supplementary data

Supplementary material for structures has been deposited with the Cambridge Crystallographic Data Centre (CCDC nos. 1947039 (1), 1947042 (2), 1947040 (3), and 1947041 (4); [email protected] or http://www.ccdc.cam.ac.uk).

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work was supported by the Undergraduate Innovation Project of Qufu Normal University (2018A045) and Shandong Provincial Natural Science Foundation, China (ZR2013BM007).