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

GJ Tustin, VGH Lafitte, CE Banks, TGJ Jones, RB Smith, J Davis, NS Lawrence

    Research output: Contribution to journalArticle

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    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.
    LanguageEnglish
    Pages5173-5182
    JournalJournal of Organometallic Chemistry
    Volume692
    Issue number23
    DOIs
    Publication statusPublished - Nov 2007

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    Tuning
    Water
    Sulfonation
    ferrocene
    Oxidation-Reduction
    Ultraviolet spectroscopy
    Isomers
    Nuclear magnetic resonance spectroscopy
    Cyclic voltammetry
    Iron
    Nuclear magnetic resonance

    Cite this

    Tustin, GJ., Lafitte, VGH., Banks, CE., Jones, TGJ., Smith, RB., Davis, J., & Lawrence, NS. (2007). Synthesis and characterisation of water soluble ferrocenes: Molecular tuning of redox potentials. 692(23), 5173-5182. https://doi.org/10.1016/j.jorganchem.2007.07.048
    Tustin, GJ ; Lafitte, VGH ; Banks, CE ; Jones, TGJ ; Smith, RB ; Davis, J ; Lawrence, NS. / Synthesis and characterisation of water soluble ferrocenes: Molecular tuning of redox potentials. 2007 ; Vol. 692, No. 23. pp. 5173-5182.
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    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.",
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    Tustin, GJ, Lafitte, VGH, Banks, CE, Jones, TGJ, Smith, RB, Davis, J & Lawrence, NS 2007, 'Synthesis and characterisation of water soluble ferrocenes: Molecular tuning of redox potentials', vol. 692, no. 23, pp. 5173-5182. https://doi.org/10.1016/j.jorganchem.2007.07.048

    Synthesis and characterisation of water soluble ferrocenes: Molecular tuning of redox potentials. / Tustin, GJ; Lafitte, VGH; Banks, CE; Jones, TGJ; Smith, RB; Davis, J; Lawrence, NS.

    Vol. 692, No. 23, 11.2007, p. 5173-5182.

    Research output: Contribution to journalArticle

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    T1 - Synthesis and characterisation of water soluble ferrocenes: Molecular tuning of redox potentials

    AU - Tustin, GJ

    AU - Lafitte, VGH

    AU - Banks, CE

    AU - Jones, TGJ

    AU - Smith, RB

    AU - Davis, J

    AU - Lawrence, NS

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    N2 - 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.

    AB - 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.

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