“Click-Triazole” Coordination Chemistry: Exploiting 1,4-Disubstituted-1,2,3-Triazoles as Ligands

Crowley, James D.; McMorran, David A.

doi:10.1007/7081_2011_67

Cited by 130 publications

(79 citation statements)

References 233 publications

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“…82 It is worth noting that due to its relative planarity and strong dipole moment, the 1,2,3-triazole has a physicochemical resemblance to the amide bond, explaining its use as a linker in biological, biochemical and carbohydrate research, 83 as well as interest in 1,2,3-triazole hydrogen bonding behaviour in anion supramolecular chemistry, which has been reviewed by Hua and Flood. 84 Although there have been a number of recent overviews of metal-chelating systems synthesised using the CuAAC reaction, 64,85,86 as a result of the rapid and recent explosion of interest in the terdentate 2,6-bis(1,2,3-trazol-4-yl)pyridine motif (btp), only limited examples of ligands containing this motif have been included. 59,71,87,88 The objective of this review, as stated above, is to address this deficit, detailing the chemistry and the applications of btp ligands which have been reported in the literature over the last few years.…”

Section: Terdentate Ligandsmentioning

confidence: 99%

The btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] binding motif: a new versatile terdentate ligand for supramolecular and coordination chemistry

2014

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Ligands containing the btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] motif have appeared with increasing regularity over the last decade. This class of ligands, formed in a one pot 'click' reaction, has been studied for various purposes, such as for generating d and f metal coordination complexes and supramolecular self-assemblies, and in the formation of dendritic and polymeric networks, etc. This review article introduces btp as a novel and highly versatile terdentate building block with huge potential in inorganic supramolecular chemistry. We will focus on the coordination chemistry of btp ligands with a wide range of metals, and how it compares with other classical pyridyl and polypyridyl based ligands, and then present a selection of applications including use in catalysis, enzyme inhibition, photochemistry, molecular logic and materials, e.g. polymers, dendrimers and gels. The photovoltaic potential of triazolium derivatives of btp and its interactions with anions will also be discussed.

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Section: Terdentate Ligandsmentioning

confidence: 99%

The btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] binding motif: a new versatile terdentate ligand for supramolecular and coordination chemistry

2014

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“…Key to the development of complexes for these applications is the design of the ligands supporting these metals. We, and others, have paid particular attention to the use of copper-catalysed coupling of alkynes and azides to form 1,2,3-triazole-based ligands [7][8][9][10] and have investigated the photophysical properties of their resultant complexes. A significant number of reports have appeared detailing the photophysical and photochemical properties of triazole-based complexes of Re(I), Ru(II) and Ir(III) [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25].…”

Section: Introductionmentioning

confidence: 99%

Towards Water Soluble Mitochondria-Targeting Theranostic Osmium(II) Triazole-Based Complexes

et al. 2016

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Abstract:The complex [Os(btzpy) 2 ][PF 6 ] 2 (1, btzpy = 2,6-bis(1-phenyl-1,2,3-triazol-4-yl)pyridine) has been prepared and characterised. Complex 1 exhibits phosphorescence (λ em = 595 nm, τ = 937 ns, φ em = 9.3% in degassed acetonitrile) in contrast to its known ruthenium(II) analogue, which is non-emissive at room temperature. The complex undergoes significant oxygen-dependent quenching of emission with a 43-fold reduction in luminescence intensity between degassed and aerated acetonitrile solutions, indicating its potential to act as a singlet oxygen sensitiser. Complex 1 underwent counterion metathesis to yield [Os(btzpy) 2 ]Cl 2 (1 Cl ), which shows near identical optical absorption and emission spectra to those of 1. Direct measurement of the yield of singlet oxygen sensitised by 1 Cl was carried out (φ ( 1 O 2 ) = 57%) for air equilibrated acetonitrile solutions. On the basis of these photophysical properties, preliminary cellular uptake and luminescence microscopy imaging studies were conducted. Complex 1 Cl readily entered the cancer cell lines HeLa and U2OS with mitochondrial staining seen and intense emission allowing for imaging at concentrations as low as 1 µM. Long-term toxicity results indicate low toxicity in HeLa cells with LD50 >100 µM. Osmium(II) complexes based on 1 therefore present an excellent platform for the development of novel theranostic agents for anticancer activity.

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“…The 2-(1-R-1H-1,2,3-triazol-4-yl)pyridine 4 and [(4-R-1H-1,2,3-triazol-1-yl)methyl]pyridine 5 (Scheme 2) click ligands have emerged as readily modied bipy and phen surrogates. 8,79,80 These bidentate click ligands form rhenium(I) complexes with a 1 : 1 metal : ligand ratio. The complexes of these ligands have wide applications in electronic 81,82 and luminescent 29,[83][84][85][86][87][88][89] materials, catalysts, [90][91][92] and in metallo-pharmaceuticals.…”

Section: 23-triazole-containing Chelators: Click Synthetic Visionmentioning

confidence: 99%

Computational investigations of click-derived 1,2,3-triazoles as keystone ligands for complexation with transition metals: a review

2018

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In recent years, metal complexes of organo 1,2,3-triazole click-derived ligands have attracted significant attention as catalysts in many chemical transformations and also as biological and pharmaceutical active agents. Regarding the important applications of these metal-organo 1,2,3-triazole-based complexes, in this review, we focused on the recently reported investigations of the structural, electronic, and spectroscopic aspects of the complexation process in transition metal complexes of 1,2,3-triazole-based click ligands. In line with this, the coordination properties of these triazole-based click ligands with transition metals were studied via several quantum chemistry calculations. Moreover, considering the complexation process, we have presented comparative discussions between the computational results and the available experimental data.

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“Click-Triazole” Coordination Chemistry: Exploiting 1,4-Disubstituted-1,2,3-Triazoles as Ligands

Cited by 130 publications

References 233 publications

The btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] binding motif: a new versatile terdentate ligand for supramolecular and coordination chemistry

The btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] binding motif: a new versatile terdentate ligand for supramolecular and coordination chemistry

Towards Water Soluble Mitochondria-Targeting Theranostic Osmium(II) Triazole-Based Complexes

Computational investigations of click-derived 1,2,3-triazoles as keystone ligands for complexation with transition metals: a review

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