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Synthesis and characterisation of water soluble ferrocenes: Molecular tuning of redox potentials

Biomedical Sciences Research Institute Computer Science Research Institute Environmental Sciences Research Institute Nanotechnology & Advanced Materials Research Institute

Tustin, GJ, Lafitte, VGH, Banks, CE, Jones, TGJ, Smith, RB, Davis, J and Lawrence, NS (2007) Synthesis and characterisation of water soluble ferrocenes: Molecular tuning of redox potentials. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 692 (23). pp. 5173-5182. [Journal article]

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DOI: 10.1016/j.jorganchem.2007.07.048

Abstract

A range of novel water-soluble alkylated ferrocene sulfonate compounds are reported. Mono- and di-sulfonation on a series of alkyl ferrocenes produced 1,1'-dimethyl ferrocene sulfonate, 1,1'-dimethyl ferrocene disulfonate, 1,1'-diethyl ferrocene sulfonate, 1,1'-diethyl ferrocene disulfonate, t-butyl ferrocene sulfonate, t-butyl ferrocene disulfonate, ethyl ferrocene sulfonate, ethyl ferrocene disulfonate, n-butyl ferrocene sulfonate and n-butyl ferrocene disulfonate. All compounds were characterized by NMR spectroscopy, UV/Vis spectroscopy and electrochemical analysis. H-1 and C-13 NMR studies have revealed the formation of several isomers with sulfonation occurring on positions alpha and beta to the alkyl substituent or on the unsubstituted cyclopentadienyl ring. Variation of the alkyl group allowed the isomeric pattern to be tuned such that the final products followed either electronic or steric control. Cyclic voltammetry of the resulting products showed that the redox potential of the iron centre can be easily manipulated by changing the substituents on the cyclopentadienyl rings. This result has significant implications in the future development of homogenous redox mediators for sensing applications. (c) 2007 Elsevier B.V. All rights reserved.

Item Type:Journal article
Faculties and Schools:Faculty of Computing & Engineering
Faculty of Computing & Engineering > School of Engineering
Research Institutes and Groups:Engineering Research Institute
Engineering Research Institute > Nanotechnology & Integrated BioEngineering Centre (NIBEC)
ID Code:14319
Deposited By:Professor James Davis
Deposited On:01 Jul 2010 10:03
Last Modified:18 Aug 2011 11:19

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