Thin-layer electrochemistry of ferrocenylbenzene derivatives: Intramolecular electronic communication

• Published in: Electrochimica acta Vol. 53; no. 26; pp. 7720 - 7725
• Main Authors: Wang, Michael C.P., Li, Yunchao, Merbouh, Nabyl, Yu, Hua-Zhong
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 01.11.2008; Elsevier
• Subjects: Chemistry; Cyclic voltammetry; Differential-pulse voltammetry; Electrochemistry; Exact sciences and technology; Ferrocenylbenzene derivatives; General and physical chemistry; Intramolecular electronic communication; Kinetics and mechanism of reactions; Thin-layer electrochemistry; Thin-layer electrochemistry; Cyclic voltammetry; Differential-pulse voltammetry; Ferrocenylbenzene derivatives; Intramolecular electronic communication; Oxidation reduction; Benzene derivatives; Differential impulse voltamperometry; Metallocene; Electrochemical detector; Electrodes; Iron Organic compounds; Sodium Perchlorates; Graphite; Electrochemical reaction; Ultraviolet visible spectrometry
• ISSN: 0013-4686; 1873-3859
• DOI: 10.1016/j.electacta.2008.05.043

Three arylferrocene derivatives, ferrocenylbenzene (MFcB), 1,3-diferrocenylbenzene (DFcB), and 1,3,5-triferrocenylbenzene (TFcB), were prepared and their redox properties systematically explored by thin-layer cyclic voltammetry (CV) and differential-pulse voltammetry (DPV). In contrast to conventional CV measurements that produced only a single pair of redox waves for all three compounds, the thin-layer technique discriminated between the multistep electron-transfer processes of DFcB and TFcB. In particular, two and three pairs of symmetric peaks were observed, respectively, when CV curves were recorded at a graphite electrode coated with a DFcB-containing and a TFcB-containing thin film of nitrobenzene and immersed in aqueous sodium perchlorate solution. These results demonstrate that the ferrocenyl moieties attached to the meta-positions of a benzene ring communicate electronically with each other, as a result of their distinct face-to-face orientations.