Products Cited in Publications Worldwide Chlorination and Oxygenation of Carbon Electrodes for Covalent Attachment of Thiol-Terminated Molecules

Chlorination and Oxygenation of Carbon Electrodes for Covalent Attachment of Thiol-Terminated Molecules

Zheng, Xin; Bolotin, Igor L; Tanriover, Beria; Rathnayake, Kumuditha; Askins, Erik J; Cabana, Jordi; Mankad, Neal P; Glusac, Ksenija D

DOI:

Abstract

This study investigated the reactivity of two carbon electrodes (glassy carbon-GC and carbon powder-CP), with iodine monochloride for surface chlorination and subsequent covalent attachment of thiol-terminated molecules, (6-mercaptohexyl)ferrocene and benzene-1,2,4,5-tetrathiol. X-ray photoelectron spectroscopy analysis revealed that the iodine monochloride treatment resulted in chlorination and iodination of both carbon electrodes, with post-reaction GC exhibiting significant Cl:C ratios. However, chlorination of either carbon electrode did not enhance reactivity with thiol-terminated molecules. For GC, inherent or anodized surface oxide groups were found to be equally effective for covalent attachment of thiol-terminated molecules through Michael addition as chlorine-termination through nucleophilic aromatic substitution. In contrast, CP, despite its lower surface reactivity, could directly tether (6-mercaptohexyl)ferrocene without pretreatment or chlorination. Furthermore, a tetrathiolate bridge was successfully employed to covalently attach a molybdenum complex to anodized GC.

Keywords

Carbon electrode modifications ; glassy carbon ; carbon black powder ; chlorination ; alkanethiols ; aromatic thiols

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A751890134029-92-897%

(6-Mercaptohexyl)ferrocene

1402.0/5g

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