Terpyridine-Functionalized Calixarenes: Synthesis, Characterization and Anion Sensing Applications

Lanthanide complexes have been developed and are reported herein. These complexes were derived from a terpyridine-functionalized calix[4]arene ligand, chelated with Tb and Eu . Synthesis of these complexes was achieved in two steps from a calix[4]arene derivative: (1) amide coupling of a calix[4]are...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2020-12, Vol.26 (1), p.87
Main Authors: Edwards, Nicola Y, Schnable, David M, Gearba-Dolocan, Ioana R, Strubhar, Jenna L
Format: Article
Language:English
Subjects:
Absorptivity
anion
Anions
Anions - analysis
Binding
Biosensing Techniques
calixarene
Calixarenes
Calixarenes - chemical synthesis
Calixarenes - chemistry
Carboxylic acids
Fluorescence
fluorescence studies
lanthanides
Lanthanoid Series Elements - chemistry
Ligands
NMR
Nuclear magnetic resonance
Pyridines - chemistry
Sensors
Spectrometry, Fluorescence
Spectroscopy
Temperature
UV–vis studies
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Summary:Lanthanide complexes have been developed and are reported herein. These complexes were derived from a terpyridine-functionalized calix[4]arene ligand, chelated with Tb and Eu . Synthesis of these complexes was achieved in two steps from a calix[4]arene derivative: (1) amide coupling of a calix[4]arene bearing carboxylic acid functionalities and (2) metallation with a lanthanide triflate salt. The ligand and its complexes were characterized by NMR ( H and C), fluorescence and UV-vis spectroscopy as well as MS. The photophysical properties of these complexes were studied; high molar absorptivity values, modest quantum yields and luminescence lifetimes on the ms timescale were obtained. Anion binding results in a change in the photophysical properties of the complexes. The anion sensing ability of the Tb(III) complex was evaluated via visual detection, UV-vis and fluorescence studies. The sensor was found to be responsive towards a variety of anions, and large binding constants were obtained for the coordination of anions to the sensor.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules26010087