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Tripodal 1,3,5-benzenetricarboxamide ligand with dipicolinic acid units and its binding with Eu(III) ions

Klangwart, Niklas; Ruijs, Céline; Hawes, Chris S.; Gunnlaugsson, Thorfinnur; Kotova, Oxana

Tripodal 1,3,5-benzenetricarboxamide ligand with dipicolinic acid units and its binding with Eu(III) ions Thumbnail


Authors

Niklas Klangwart

Céline Ruijs

Thorfinnur Gunnlaugsson

Oxana Kotova



Abstract

The synthesis and characterisation of tripodal ligand 1 containing 1,3,5-benzenetricarboxamide core and diethyl 4-(phenylethynyl)pyridine-2,6-dicarboxylate is described. The crystal structure of the intermediate tripodal molecule 7 exhibits an unusual staggered hydrogen-bonded chain motif instead of the anticipated helical assembly. We studied the basic photophysical properties of 1 in solvents of various polarity including CH3OH, CH3CN, DMSO, and CHCl3. The self-assembly experiments between 1 and Eu(CF3SO3)(3)center dot 6H(2)O confirmed the formation of metal-ligand self-assembly species in the solution of CH3CN. It was also shown that the excitation of the Eu(III)-centred emission in such species occurred through the energy transfer from the ligand acting as an antenna to the metal centre. The binding constant values were evaluated using the nonlinear regression analysis software SPECFIT (R), and their values correspond to those previously observed for the assemblies between 2,6-dipicolinic acid derivatives and lanthanide ions.

This work describes the synthesis of tripodal 1,3,5-benzenetricarboxamide ligand with dipicolinic acid units and its binding with Eu(III) ions in solution. The photophysical properties of the target tripodal ligand were studied in solvents of various polarity. The self-assembly experiments between the ligand and Eu(III) ions in solution confirmed the formation of luminescent metal-ligand self-assembly species.

Citation

Klangwart, N., Ruijs, C., Hawes, C. S., Gunnlaugsson, T., & Kotova, O. (2022). Tripodal 1,3,5-benzenetricarboxamide ligand with dipicolinic acid units and its binding with Eu(III) ions. Supramolecular Chemistry, 34(1), 10-19. https://doi.org/10.1080/10610278.2023.2177162

Journal Article Type Article
Acceptance Date Feb 2, 2023
Online Publication Date Feb 24, 2023
Publication Date Jan 2, 2022
Publicly Available Date May 30, 2023
Journal Supramolecular Chemistry
Print ISSN 1061-0278
Publisher Taylor and Francis
Volume 34
Issue 1
Pages 10-19
DOI https://doi.org/10.1080/10610278.2023.2177162
Keywords General Chemistry
Publisher URL https://www.tandfonline.com/doi/full/10.1080/10610278.2023.2177162

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