A polydentate ligand based on 2,2’-dipyridylamine unit linked benzo-15-crown-5; alkali and transition metal complexes; photoresponsive ligand; antimicrobial evaluation against pathogenic microorganisms

Abstract

New double-armed benzo-15-crown-5 compound (L) was successfully synthesized from 4’,5’-bis(bromethyl)benzo-15- crown-5 with 2,2’-dipyridylamine. The synthesized host molecule (L), the dipyridylamine unit was able to coordinate Ni2+, Cu2+ and Ag+ metal cations, whereas the crown ether moiety bound with the alkali metal cations (Na+ and K+). The structures of the ligand (L), alkali metal complexes (NaL and KL2) and transition metal complexes ([NiLOAc], [CuLOAc] and [AgLNO3]) were characterized by spectroscopic methods. NMR and mass data provided exact evidence of complex formation through both coordination centers of the new ligand (L). Both parts (dipyridyl and crown ether) were linked to form a potential fuorescent-sensing compound (L) for metal cations. Therefore, to investigate the metal selectivity, diferent metal cations (Na+, Mg2+, K+, Ba2+, Cr3+, Fe3+, Co2+, Ni2+, Cu2+, Zn2+ and Ag+) and the new sensing compound (L) fuorescence spectra were recorded. Coordinations with Zn2+, Fe3+ and Cu2+ induced obvious changes on their increasing concentrations in fuorescence spectra. Crown ethers, as representatives of supramolecular compounds, are also promising antibacterial active compounds because of their ionophoric features. Synthesized ligand (L) and complexes (NaL, KL2, [NiLOAc], [CuLOAc] and [AgLNO3]) also proved to be adjuvants that helped to overcome antimicrobial resistance in a range of bacteria and yeast. The antimicrobial activity of compounds was screened in vitro against some pathogenic Grampositive bacteria, some Gram-negative bacteria and yeast.