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Keywords:

  • amines;
  • chemosensors;
  • fluorescence spectroscopy;
  • Heck reaction;
  • UV/Vis spectroscopy

Abstract

In this work, three new tripodal triphenylamine dyes are presented that are capable of reversibly binding amines and diamines to form hemiaminals through a covalent bond. The dyes were synthesized by the Heck reaction and possess stilbene units with one, two, or three trifluoroacetyl groups as receptor moieties. Their interaction with amines and diamines led to changes in their absorption and emission properties, which were detected by UV/Vis and fluorescence spectroscopy. The influence of the number of trifluoroacetyl receptor moieties on the selectivity and sensitivity of the dyes was studied. Enhanced sensitivity and selectivity for diaminoalkanes was found for the dye we have labeled Tripod-1, with three chemically reactive trifluoroacetyl groups, related to only one or two trifluoroacetyl groups in the dye molecule.