Fluorescence "turn-on" sensing of carboxylate anions with oligothiophene-based o-(carboxamido)trifluoroacetophenones.
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.
Kim
Dae-Sik
DS
Department of Chemistry and Center for Integrated Molecular Systems, POSTECH, San 31 Hyoja-dong, Pohang 790-784, Republic of Korea.
Ahn
Kyo Han
KH
D000098:Acetophenones / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D000838:Anions / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D012680:Sensitivity and Specificity; D013050:Spectrometry, Fluorescence; D013876:Thiophenes / Q000737:chemistry*; D017186:Titrimetry
D000098:Acetophenones; D000577:Amides; D000838:Anions; D002264:Carboxylic Acids; D005456:Fluorescent Dyes; D006845:Hydrocarbons, Fluorinated; D013876:Thiophenes