4.7 Article

Fluorescence turn-on sensing of carboxylate anions with oligothiophene-based o-(carboxamido)trifluoroacetophenones

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 17, Pages 6831-6834

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo801178y

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Funding

  1. Korea Health Industry Development Institute [A05-0426-B20616-05N1-00010A]
  2. Korea Research Foundation [KRF-2005-070-C00078]
  3. Korea Health Promotion Institute [A050426] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
  4. National Research Foundation of Korea [2005-070-C00078] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)

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o-(Carboxamido)trifluoroacetophenones containing ter- or pentathiophene moiety as a fluorophore exhibit fluorescence enhancement upon binding carboxylate anions. Particularly, the terthiophene derivative shows a large fluorescence enhancement factor (FEF = 120). The enhancement is explained by intramolecular H-bonding stabilization of an anion-ionophore adduct, through which a possible quenching process, the n-pi* transition from the trifluoroacetophenone moiety, is eliminated.

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