Synthesis, structural, photophysical and electrochemical studies of various d-metal complexes of btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] ligands that give rise to the formation of metallo-supramolecular gels

Byrne, J.; Kitchen, Jonathan A.; Kotova, Oxana; Leigh, Vivienne; Bell, Alan P.; Boland, John J.; Albrecht, Martin; Gunnlaugsson, Thorfinnur

doi:10.1039/c3dt52309h

Cited by 45 publications

(52 citation statements)

References 77 publications

(97 reference statements)

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“…61 The complex displayed a distorted octahedral geometry and signals in the 1 H-NMR (600 MHz, CD 3 CN) spectrum were broadened and shifted as a result of the metal ion's paramagnetism. To the best of our knowledge, this is the only example of a Ni(II)-btp complex.…”

Section: Nickelmentioning

confidence: 99%

“…Given the fact that the btp ligand can be readily derivatised at the 1-position of the triazole units, this ligand is an excellent candidate for such endeavours. 60,61 This is further fuelled by the rapid developments that have occurred within the field of metallo-supramolecular chemistry. Here, most architectural shapes and topologies have been accessed; hence, the focus has increasingly moved towards developing new methods for functionalising ligands, and synthesis that is modular, facile and high-yielding.…”

Section: Terdentate Ligandsmentioning

confidence: 99%

“…These complexes displayed only ligandcentred emission in solution at room temperature, but in CH 3 CN glasses at 77 K showed behaviour similar to that of terpy analogues, resulting in emission due to Pt(II)-Pt(II) stacking interactions as well as interactions between the aromatic ligands. 61,121 Yam and co-workers reported the synthesis of a series of chloroplatinum(II) complexes [Pt(btp)Cl]X (X = Cl À , PF 6 À , CF 3 SO 3 À ) with ligands 1, 3a, 5, 7 and 32a-c, as well as a range of related luminescent alkynylplatinum(II) complexes. The chloroplatinum(II) complexes were found to be non-luminescent in solution at room temperature, however, the alkynylplatinum(II) complexes were observed to be luminescent, displaying large Stokes shifts, , the only Pd(II) complex of a discrete btp system in the literature, of which a crystal structure was also obtained.…”

Section: Platinummentioning

confidence: 99%

“…61 This property theoretically allows for robust functionalisation of a product in this position after a desirable oxidation potential has been achieved, e.g. for multifunctional systems.…”

Section: Rutheniummentioning

confidence: 99%

“…The Cl À was located approximately 1341 out of the plane of the C-H bond in all cases. 61 Hecht and co-workers described oligomeric systems 48 (see Fig. 10) which behaved as helically folding foldamers as a result of p-p stacking interactions.…”

Section: Interactions With Anionsmentioning

confidence: 99%

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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: Nickelmentioning

confidence: 99%

Section: Terdentate Ligandsmentioning

confidence: 99%

Section: Platinummentioning

confidence: 99%

“…61 This property theoretically allows for robust functionalisation of a product in this position after a desirable oxidation potential has been achieved, e.g. for multifunctional systems.…”

Section: Rutheniummentioning

confidence: 99%

Section: Interactions With Anionsmentioning

confidence: 99%

See 3 more Smart Citations

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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Synthesis, Characterisation and Antimicrobial Studies of some 2,6‐bis(1,2,3‐Triazol‐4‐yl)Pyridine Ruthenium(II) “Click” Complexes

et al. 2019

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A family of homo-and hetero-leptic ruthenium(II) bis-tridentate complexes generated from 2,6-bis(1-R-1,2,3triazol-4-yl)pyridine "click" ligands (R-tripy) with either aliphatic or aromatic substituents were synthesized (35-97%).The family of compounds were tested for antimicrobial activity in vitro against both Staphylococcus aureus (S. aureus, ATCC 25923) and Escherichia coli (E. coli, ATCC 25922) bacteria. The antibacterial activity showed dependence on the alkyl chain length of the [Ru(R-tripy) 2 ] 2 + (Cl À ) 2 complexes, with the best activity occurring for the three complexes featuring either hexyl or heptyl substituents on the ligands. The minimum inhibitory concentrations (MICs) for the most active mononuclear complex [Ru(hexyltripy)(heptyltripy)] 2 + (Cl À ) 2 were 2 μg/mL and 8 μg/mL respectively against S. aureus and E. coli. The three most active complexes were screened against other pathogenic bacteria, including two strains of Methicillin resistant S. aureus (MRSA). The compounds showed good activity against the Gram positive strains (MIC = 4-8 μg/mL) but were less effective against Gram negative bacteria (MIC = 8-16 μg/mL). Cytotoxicity experiments with eukaryotic cells lines (cancer and skin) suggested that the R-tripy ligands and complexes were reasonably cytotoxic (IC 50 = 2-25 μM) and displayed little to no selectivity for bacteria over eukaryotic cells lines.[a] Q. /phen ligands and have been used to develop metal complexes for a range of applications. [19] Two of the complexes ([Ru(hexpytri) 3 ] 2 + and [Ru(octpytri) 3 ] 2 + (where hexpytri = 2-(1hexyl-1H-1,2,3-triazol-4-yl)pyridine and octpytri = 2-(1-octyl-1H-1,2,3-triazol-4-yl)pyridine) showed good antimicrobial activity against Gram positive S. aureus and MRSA (MICs = 1-8 μg/mL) but little to no activity against Gram negative bacteria (MIC = 16-> 128 μg/mL). The mer and fac isomers of the complexes showed no difference in activity. Propidium iodide assays and transmission electron microscopy (TEM) indicated that the main mode of action for these ruthenium(II) R-pytri complexes was cytoplasmic membrane disruption.Building on that work, herein we report the synthesis of a structurally related family of ruthenium(II) "click" complexes generated from tridentate 2,6-bis(1-R-1H-1,2,3-triazol-4-yl) pyridine (R-tripy) ligands (Scheme 1). The new bis-tridentate ruthenium(II) complexes, [Ru(R-tripy) 2 ] 2 + (Cl À ) 2 , retain most of the structural features of the previously studied [Ru(R-pytri) 3 ] 2 + (X À ) 2 complexes but they do not form isomers (either enantiomers or diastereomers). The new "click" complexes were tested for antimicrobial activity in vitro against both S. aureus and Escherichia coli (E. coli) bacteria. Additionally, the cytotoxicity of the most active complexes was examined against three human cell lines. Results and DiscussionSynthesis of Tridentate 2,6-bis(1-R-1,2,3-triazol-4-yl)pyridine (R-tripy) Ligands . TEM images a) untreated S. aureus b) S. aureus incubated with 4 μg/mL of [Ru(hexyltripy)(heptyltripy)] 2 + , c) and d) S...

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Formation of Self‐Templated 2,6‐Bis(1,2,3‐triazol‐4‐yl)pyridine [2]Catenanes by Triazolyl Hydrogen Bonding: Selective Anion Hosts for Phosphate

et al. 2016

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We report the remarkable ability of 2,6-bis(1,2,3triazol-4-yl)pyridine (btp)compounds 2 with appended olefin amide arms to self-template the formation of interlocked [2]catenane structures 3 in up to 50 %yield when subjected to olefin ring-closing metathesis in CH 2 Cl 2 .X -ray diffraction crystallography enabled the structural characterization of both the [2]catenane 3a and the non-interlocked macrocycle 4a. These [2]catenanes showed selective triazolyl hydrogen-bonding interactions with the tetrahedral phosphate anion when screened against arange of ions; 3a,b are the first examples of selective [2]catenane hosts for phosphate.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under http://dx.

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Synthesis, structural, photophysical and electrochemical studies of various d-metal complexes of btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] ligands that give rise to the formation of metallo-supramolecular gels

Cited by 45 publications

References 77 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

Synthesis, Characterisation and Antimicrobial Studies of some 2,6‐bis(1,2,3‐Triazol‐4‐yl)Pyridine Ruthenium(II) “Click” Complexes

Formation of Self‐Templated 2,6‐Bis(1,2,3‐triazol‐4‐yl)pyridine [2]Catenanes by Triazolyl Hydrogen Bonding: Selective Anion Hosts for Phosphate

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