Synthesis, photophysical and assembly studies of novel luminescent lanthanide(III) complexes of 1,2,3-triazolyl-pyridine-2,6-dicarboxamide-based ligands
Synthesis, photophysical and assembly studies of novel luminescent lanthanide(III) complexes of 1,2,3-triazolyl-pyridine-2,6-dicarboxamide-based ligands
The well-known lanthanide-binding motif, 2,6-pyridinedicarboxamide, has been functionalised with peripheral substituents using copper-catalysed azide alkyne coupling (CuAAC) to develop new symmetrical ‘clicked’ N2,N6-bis((1-(X)-1H-1,2,3,-triazol-4-yl)methyl)pyridine- 2,6-dicarboxamide (where X = ethyl (1) benzyl (2) and 2-naphthyl (3)). These ligands have been successfully coordinated with trivalent lanthanide ions (europium, terbium, and lanthanum) forming [Ln(L)3](CF3SO3)3 complexes. The ligands act as effective antennae for Eu3+ and Tb3+ complexes, which exhibit the characteristic sensitised emission profiles. The ability of 1–3 to assemble into 1:3 M:L systems in solution was investigated using UV-Vis, fluorescence, and NMR. Finally, density functional calculations of the ground state La3+ complexes have been carried out and show similar geometry and coordination parameters to those with available crystallographic data. The facile and modular synthesis of these ‘clicked’ PDC-based ligands makes these compounds excellent candidates for luminescent supramolecular materials development.
2,6-pyridinedicarboxamide, Lanthanides, luminescent materials, supramolecular architectures, triazole ‘click’ chemistry and
160-173
O’Neil, Alex T.
10a0437d-7247-4011-af4d-86635d15ca47
Zhang, Ningjin
96cb5378-d12f-4ecb-84cf-6be24322956a
Harrison, John A.
0b60ae3e-b9b3-43fc-b41e-b69a72fa12cb
Goldup, Stephen M.
0a93eedd-98bb-42c1-a963-e2815665e937
Kitchen, Jonathan A.
3999f5cb-d53e-4c51-b750-627bd2a1b9b6
O’Neil, Alex T.
10a0437d-7247-4011-af4d-86635d15ca47
Zhang, Ningjin
96cb5378-d12f-4ecb-84cf-6be24322956a
Harrison, John A.
0b60ae3e-b9b3-43fc-b41e-b69a72fa12cb
Goldup, Stephen M.
0a93eedd-98bb-42c1-a963-e2815665e937
Kitchen, Jonathan A.
3999f5cb-d53e-4c51-b750-627bd2a1b9b6
O’Neil, Alex T., Zhang, Ningjin, Harrison, John A., Goldup, Stephen M. and Kitchen, Jonathan A.
(2021)
Synthesis, photophysical and assembly studies of novel luminescent lanthanide(III) complexes of 1,2,3-triazolyl-pyridine-2,6-dicarboxamide-based ligands.
Supramolecular Chemistry, 33 (5), .
(doi:10.1080/10610278.2021.1955120).
Abstract
The well-known lanthanide-binding motif, 2,6-pyridinedicarboxamide, has been functionalised with peripheral substituents using copper-catalysed azide alkyne coupling (CuAAC) to develop new symmetrical ‘clicked’ N2,N6-bis((1-(X)-1H-1,2,3,-triazol-4-yl)methyl)pyridine- 2,6-dicarboxamide (where X = ethyl (1) benzyl (2) and 2-naphthyl (3)). These ligands have been successfully coordinated with trivalent lanthanide ions (europium, terbium, and lanthanum) forming [Ln(L)3](CF3SO3)3 complexes. The ligands act as effective antennae for Eu3+ and Tb3+ complexes, which exhibit the characteristic sensitised emission profiles. The ability of 1–3 to assemble into 1:3 M:L systems in solution was investigated using UV-Vis, fluorescence, and NMR. Finally, density functional calculations of the ground state La3+ complexes have been carried out and show similar geometry and coordination parameters to those with available crystallographic data. The facile and modular synthesis of these ‘clicked’ PDC-based ligands makes these compounds excellent candidates for luminescent supramolecular materials development.
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More information
Accepted/In Press date: 27 June 2021
e-pub ahead of print date: 18 August 2021
Additional Information:
Funding Information:
We would like to thank Ian Stewart for collecting Mass Spec., the New Zealand Ministry of Business, Innovation and Employment and the Royal Society Te Apārangi, for a Catalyst: Seeding fund.
Publisher Copyright:
© 2021 Informa UK Limited, trading as Taylor & Francis Group.
Keywords:
2,6-pyridinedicarboxamide, Lanthanides, luminescent materials, supramolecular architectures, triazole ‘click’ chemistry and
Identifiers
Local EPrints ID: 469423
URI: http://eprints.soton.ac.uk/id/eprint/469423
ISSN: 1061-0278
PURE UUID: b371675a-f0e7-4272-8690-4d25f357cee2
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Date deposited: 14 Sep 2022 16:49
Last modified: 05 Jun 2024 19:08
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Contributors
Author:
Alex T. O’Neil
Author:
Ningjin Zhang
Author:
John A. Harrison
Author:
Jonathan A. Kitchen
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