Synthesis and characterization of ferrocene functionalized transition metal dithiocarbamate complexes: Investigations of antimicrobial, electrochemical properties and a new polymorphic form of [Cu{κ2S,S–S2CN(CH2C4H3O)CH2Fc}2]

•New ferrocenyl bearing transition metal dithiocarbamate complexes were prepared.•Anti-microbial and electrochemical properties were explored.•Single crystal XRD was used to detect new polymorphic form.•S/lp⋯π and C–H…π interactions stabilizes crystal packing.•The TGA/DTA analysis reveals the formation of metallic iron.

A straightforward single pot reaction of N-methylaryl-N-methylferrocenyl amine (L1-L3), CS2 and M(OAc)2 in Et3N at room temperature led to the formation of [M{κ2S,S–S2CN(CH2R)CH2Fc}n] {M = CoIII, R = 1-naphthyl, (1), 3-pyridyl (2), 2-furyl (3); M = NiII, R = 1-naphthyl, (4), 3-pyridyl (5), 2-furyl (6); M = CuII, R = 1-naphthyl, (7), 2-furyl (8); M = ZnII, R = R = 1-naphthyl, (9); n = 3 for 1–3 and n = 2 for 4–9}. L1-L3 and 1–9 were characterized by microanalysis and standard spectroscopic methods viz. MS, IR, 1H, 13C, DEPT 135 NMR, UV–vis. absorption and emission spectroscopy. Single crystal X-ray diffraction technique was used to detect a new polymorphic form of 8, sustained by significant S/lp⋯π and C–H…π intermolecular interactions. All the compounds were screened against a panel of microbes viz. Staphylococus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa, Candida albicans and Aspergillus niger. Remarkably, L1, 4 and 8 were found to have better antibacterial activity against S. aureus than Ciprofloxacin, while compound 5 was found to be as good an antifungal agent as Flucanazole against C. albicans. All the compounds display a single quasi-reversible cyclic voltammograms and formal redox potentials in the range of 407 to 224 mV vs Ag/Ag+ (CH3CN).

Graphical abstractNew ferrocenyl bearing transition metal dithiocarbamate complexes were prepared. Anti-microbial and electrochemical properties were explored. Single crystal XRD was used to detect a new polymorphic form. All the compounds display a single quasi-reversible cyclic voltammograms in the range of 407 to 224 mV and interesting anti-bacterial properties against a panel of microbes.Figure optionsDownload full-size imageDownload as PowerPoint slide