Fluorescence Enhancement Detection of Underivatized Amino Acids Using a Trifluoroacetophenone-Based Tripodal Fluoroionophore

Abstract

A tripodal fluoroionophore based on a hexasubstituted benzene unit having two trifluoroacetophenone groups and a pyrenyl moiety was synthesized, and its characteristics as fluorogenic reagent or component of an ISE or optode membrane towards several underivatized amino acids were examined. In a solid-liquid extraction experiment in acetonitrile, the fluorescence enhancement response was observed in the order of Phe, Cys, and Gly. On the other hand, the PVC-based polymeric membrane applied in ISE showed Phe selectivity with a monoanionic Nernstian response, supporting the assumption that the ionophore binds Phe in its anionic form. It is demonstrated that the optode membrane based on this fluoroionophore shows fluorescence enhancement response towards Phe or Cys in a flow-system.

Chemosensor for the optical detection of aliphatic amines and diamines

“…6 Suzuki et al developed a trifluoroacetophenone-based tripodal sensor molecule for the detection of amino acids. 7 The preparation of an amine-selective chemosensor with a (trifluoroacetyl)azobenzene reporter group incorporated into a dendrimer was reported by Beil and Zimmerman. 8 Here we report on the synthesis and characterisation of a new optical sensor based on two chemosensor dyes and their use for the selective detection of aliphatic amines and diamines.…”

Star‐Shaped Tripodal Chemosensors for the Detection of Aliphatic Amines

“…Keywords: amines · chemosensors · fluorescence spectroscopy · Heck reaction · UV/Vis spectroscopy cle formation and led, therefore, to the observed modified selectivity. A trifluoroacetophenone-based tripodal sensor molecule for the detection of amino acids was developed by Suzuki et al [14,15] They introduced three receptor groups for simultaneous binding of the amino and the carboxylate groups of an amino acid in the anionic form. Another tripodal trifluoroacetophenone derivative for use in ion-selective electrode membranes was presented by Ahn et al [16] With all this in mind, we decided to develop an optical chemosensor with three trifluoroacetyl groups for amine detection.…”