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

Seiichi Nishizawa, Ying Yu Cui, Masakazu Minagawa, Kotaro Morita, Yuichi Kato, Shinichiro Taniguchi, Ryo Kato, Norio Teramae

Research output: Contribution to journalArticle

50 Citations (Scopus)

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 thefluorophore 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.

Original languageEnglish
Pages (from-to)866-870
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number5
Publication statusPublished - 2002 May 21

ASJC Scopus subject areas

  • Chemistry(all)

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