Synthesis, crystal structures, electrochemical properties, and complexation of ferrocene-based compounds: 1,2-bis(dimethyldithiocarbamate)ferrocene and 1,2-bis(benzothiazol-2-ylthio)ferrocene

Publication date: Available online 9 September 2019Source: Journal of Organometallic ChemistryAuthor(s): Ryo Horikoshi, Ryo Sumitani, Tomoyuki MochidaAbstractFerrocene-based metalloligands have various applications in material sciences due to their stability in air and redox active properties. Two ferrocene-based compounds, 1,2-bis(dimethyldithiocarbamate)ferrocene (1) and 1,2-bis(benzothiazol-2-ylthio)ferrocene (2), were synthesized from 1,1′-dibromoferrocene and the corresponding disulfides via two steps. The reaction of 1 with PdCl2(PhCN)2 formed a 1:1 metal:ligand complex, [PdCl2(1)]. Compounds 1,2, and [PdCl2(1)] were structurally characterized by single-crystal X-ray diffraction, and their redox potentials were measured by cyclic voltammetry. Two pseudopolymorphs, ethanol-solvated 1(C2H5OH)0.33 and non-solvated 1, were obtained by recrystallization from ethanol. The Xray structure of [PdCl2(1)] showed that the Pd(II) center was chelated by 1 with two thioketone sulfur atoms; 1 showed two irreversible oxidationpeaks at 0.17 and 0.41 V (vs. Fe(Cp)2/Fe(Cp)2+), corresponding to oxidation of the two substituents and ferrocene, respectively.Conversely, 2 showed a quasi-reversible redox potential at E1/2 = 0.40 V,attributable to the ferrocene moiety. [PdCl2(1)] showed two irreversible oxidation peaks at 0.48 and 0.64 V and a reduction peak at 0.52 V (vs.Fe(Cp)2/Fe(Cp)2+).Graphical abstract
Source: Journal of Organometallic Chemistry - Category: Chemistry Source Type: research

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