Using hydrazine to link ferrocene with Re(CO)3: A modular approach

• Published in: Journal of organometallic chemistry Vol. 818; pp. 145 - 153
• Main Authors: Chanawanno, Kullapa, Rhoda, Hannah M., Hasheminasab, Abed, Crandall, Laura A., King, Alexander J., Herrick, Richard S., Nemykin, Victor N., Ziegler, Christopher J.
• Format: Journal Article
• Language: English
• Published: Switzerland Elsevier B.V 01-09-2016
• Subjects: Density functional theory; Electrochemistry; Ferrocene; Schiff base conjugate; Tricarbonyl rhenium(I); Electrochemistry; Schiff base conjugate; Density functional theory; Tricarbonyl rhenium(I); Ferrocene; tricarbonyl rhenium(I); electrochemistry; density functional theory
• ISSN: 0022-328X; 1872-8561
• DOI: 10.1016/j.jorganchem.2016.06.004

Acetyl ferrocene and diacetyl ferrocene both readily react with an excess of hydrazine to afford the corresponding hydrazone compounds. These compounds can then be linked to Re(CO)3 via a metal-mediated Schiff base reaction, resulting in a series of ferrocene-Re(CO)3 conjugates with different stoichiometries. Conjugates with 1:1, 1:2, and 2:1 ferrocene: Re(CO)3 ratios can be produced via this “modular” type synthesis approach. Several examples of these conjugates were structurally characterized, and their spectroscopic, electrochemical, and spectroelectrochemical behaviors were investigated. The electronic structures of these compounds were also probed using DFT and TDDFT calculations.
Acetyl ferrocene and diacetyl ferrocene both readily react with an excess of hydrazine to afford the corresponding hydrazone compounds, which can be coupled to Re(CO)3 groups via Schiff base formation reactions. [Display omitted]
•A series of ferrocene-Re(CO)3 conjugates was synthesized and characterized.•Compounds with various ferrocene: Re(CO)3 ratios were made via a modular approach.•The spectroscopic, redox, and spectroelectrochemical behaviors were studied.•The electronic structures were also probed using DFT and TDDFT calculations.