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Issue 5, 2002
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Conversion of thioureas to fluorescent isothiouronium-based photoinduced electron transfer sensors for oxoanion sensing

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Abstract

A convenient conversion is described of thiourea-based receptors to fluorescent isothiouronium-based photoinduced electron transfer (PET) sensors for oxoanion sensing. Naphthalene- or anthracene-functionalized mono-isothiouroniums are synthesized from the corresponding thioureas, in which the fluorophore is connected to the sulfur atom of the thiourea moiety by a methylene or an ethylene spacer. Even though all of the isothiouroniums with a methylene spacer readily decompose in MeOH upon excitation of the fluorophore moiety, the isothiouronium with an ethylene spacer shows good stability under identical conditions. The naphthyl isothiouronium with an ethylene spacer shows a significant fluorescence enhancement upon formation of a 1 ∶ 1 complex with oxoanions in MeOH, and the selectivity follows the order of hydrogen phosphate > acetate ≫ dihydrogen phosphate ≫ chloride. The results in the present work indicate that various types of fluorescent PET sensors might be readily obtainable from non-fluorescent thiourea-based receptors by the introduction of appropriate fluorophores at the sulfur atom of thiourea-binding sites.

Graphical abstract: Conversion of thioureas to fluorescent isothiouronium-based photoinduced electron transfer sensors for oxoanion sensing

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Publication details

The article was received on 18 Feb 2002, accepted on 21 Mar 2002 and first published on 05 Apr 2002


Article type: Paper
DOI: 10.1039/B201704K
Citation: J. Chem. Soc., Perkin Trans. 2, 2002,0, 866-870
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    Conversion of thioureas to fluorescent isothiouronium-based photoinduced electron transfer sensors for oxoanion sensing

    S. Nishizawa, Y. Cui, M. Minagawa, K. Morita, Y. Kato, S. Taniguchi, R. Kato and N. Teramae, J. Chem. Soc., Perkin Trans. 2, 2002, 0, 866
    DOI: 10.1039/B201704K

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