Rhenium(I) complexes of readily functionalized bidentate pyridyl-1,2,3-triazole “click” ligands: A systematic synthetic, spectroscopic and computational study

Kim, Tae Y.; Elliott, Anastasia B. S.; Shaffer, Karl J.; McAdam, C. John; Gordon, Keith C.; Crowley, James D.

doi:10.1016/j.poly.2012.05.003

Cited by 68 publications

(84 citation statements)

References 74 publications

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“…bis(phenanthridinylmethyl)amine (bpm) [22,[43][44][45]. However, other polyazaheterocycles have also been developed, such as 1-R-4-(2-pyridyl)-1,2,3-triazole (pyta) and its derivatives [46][47][48]. More recently, Re(I) tricarbonyl complexes incorporating 5,5'-disubstituted 3,3'-bisisoxazole have also been described [49].…”

Section: Spectroscopic Properties Of Luminescent Re(i) Tricarbonyl Comentioning

confidence: 99%

Re(I) carbonyl complexes: Multimodal platforms for inorganic chemical biology

Hostachy

Policar

Delsuc

2017

Coordination Chemistry Reviews

113

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Bio-imaging, by enabling the visualization of biomolecules of interest, has proved to be highly informative in the study of biological processes. Although fluorescence microscopy is probably one of the most used techniques, alternative methods of imaging, providing complementary information, are emerging. In this context, metal complexes represent valuable platforms for multimodal imaging, since they may combine interesting spectroscopic features and biologically relevant functionalization on a single molecular core. In particular, d6 low-spin rhenium tri-carbonyl complexes display unique luminescence and vibrational properties, and can be readily functionalized. Here we review their applications and potential as probes or drugs relying on their photophysical properties, before focusing on their use as multimodal probes for the labelling and imaging of peptides and proteins.

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Section: Spectroscopic Properties Of Luminescent Re(i) Tricarbonyl Comentioning

confidence: 99%

Re(I) carbonyl complexes: Multimodal platforms for inorganic chemical biology

Hostachy

Policar

Delsuc

2017

Coordination Chemistry Reviews

113

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“…It has been shown that the triazole ring substituent effect is not considerable on the metric properties of rhenium complexes and so it can be deduced that side-arm substitution leads to little electronic tuning of the ligand. Furthermore, in these [(4-R-1H-1,2,3-triazol-1-yl)methyl]pyridine 5 set of ligands, it was found that the N py -Re bond length value (2.198 (5) Clearly speaking, regardless of whether the triazole is coordinated to the Re center, the obtained values of the Re-N2 trz and Re-N2 trz -N4 py bond lengths and angles in the entire series of regular ve-membered rhenium click complexes 63,64,97,183,184 (Schemes 27 and 29) were very near to those of inverse sixmembered rhenium click complexes, and this feature has been also studied and conrmed in the Pd(II) complexes of these ligands.…”

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confidence: 95%

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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“…The synthesis of the [2 + 1]‐type rhenium carbonyl complexes was achieved by the reaction of ligand L 1 with [Re(CO) 3 (py) 3 ]OTf (where py = pyridine, Scheme A) . The [Re(CO) 3 L x (py)] complexes can also be prepared by bromide abstraction of the [Re(CO) 3 L x Br] complex with silver triflate in the presence of pyridine (Scheme ) …”

Section: Resultsmentioning

confidence: 99%

Rhenium and technetium tricarbonyl complexes of 1,4‐Substituted pyridyl‐1,2,3‐triazole bidentate ‘click’ ligands conjugated to a targeting RGD peptide

Connell

Hayne

Ackermann

et al. 2013

Labelled Comp Radiopharmac

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New 1,4-substituted pyridyl-1,2,3-triazole ligands with pendent phenyl isothiocyanate functional groups linked to the heterocycle through a short methylene or longer polyethylene glycol spacers were prepared and conjugated to a peptide containing the arginine-glycine-aspartic acid peptide motif. Rhenium and technetium carbonyl complexes, [M(CO)3 L(x) (py)](+) (where M = Re(I) or (99m) Tc(I) ; L(x) = 1,4-substituted pyridyl-1,2,3-triazole ligands and py = pyridine) were prepared. One rhenium complex has been characterized by X-ray crystallography, and the luminescent properties of [M(CO)3 L(x) (py)](+) are reported.

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Rhenium(I) complexes of readily functionalized bidentate pyridyl-1,2,3-triazole “click” ligands: A systematic synthetic, spectroscopic and computational study

Cited by 68 publications

References 74 publications

Re(I) carbonyl complexes: Multimodal platforms for inorganic chemical biology

Re(I) carbonyl complexes: Multimodal platforms for inorganic chemical biology

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

Rhenium and technetium tricarbonyl complexes of 1,4‐Substituted pyridyl‐1,2,3‐triazole bidentate ‘click’ ligands conjugated to a targeting RGD peptide

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