Fluorescent palladium(<scp>ii</scp>) and platinum(<scp>ii</scp>) NHC/1,2,3-triazole complexes: antiproliferative activity and selectivity against cancer cells

Schlagintweit, Jonas F.; Jakob, Christian; Meighen-Berger, Kevin; Gronauer, Thomas F.; Muñoz, Angela Weigert; Weiß, Vanessa; Feige, Matthias J.; Sieber, Stephan A.; Correia, João D. G.; Kühn, Fritz E.

doi:10.1039/d0dt04114a

Cited by 11 publications

(10 citation statements)

References 51 publications

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“…The use of ligands with NHC-type structures has also been reported by Kühn et al [ 87 ] where a fluorescent Pd(II) complex bearing 4-methylene-7-methoxycoumarin (MMC) and 2,6-diisopropylphenyl (Dipp) substituted NHC/1,2,3-triazole hybrid ligands 78 , shown in Figure 21 , was described. Complex 78 has a quantum efficiency of fluorescence of 7% in acetonitrile at room temperature.…”

Section: Orthopalladated Ligandsmentioning

confidence: 61%

Luminescence and Palladium: The Odd Couple

Dalmau

Urriolabeitia

2023

Molecules

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The synthesis, photophysical properties, and applications of highly fluorescent and phosphorescent palladium complexes are reviewed, covering the period 2018–2022. Despite the fact that the Pd atom appears closely related with an efficient quenching of the fluorescence of different molecules, different synthetic strategies have been recently optimized to achieve the preservation and even the amplification of the luminescent properties of several fluorophores after Pd incorporation. Beyond classical methodologies such as orthopalladation or the use of highly emissive ligands as porphyrins and related systems (for instance, biladiene), new concepts such as AIE (Aggregation Induced Emission) in metallacages or in coordination-driven supramolecular compounds (CDS) by restriction of intramolecular motions (RIM), or complexes showing TADF (Thermally Activated Delayed Fluorescence), are here described and analysed. Without pretending to be comprehensive, selected examples of applications in areas such as the fabrication of lighting devices, biological markers, photodynamic therapy, or oxygen sensing are also here reported.

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Section: Orthopalladated Ligandsmentioning

confidence: 61%

Luminescence and Palladium: The Odd Couple

Dalmau

Urriolabeitia

2023

Molecules

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“…To date, triazolylidene metal complexes have been mainly applied in catalysis. 3 However, their potential in other fields such as, photochemistry, [6][7][8][9] supramolecular chemistry, 10,11 and electrocatalysis 12 has been recently demonstrated. Most examples of triazolylidene complexes reported in the literature contain second-and third-row transition metals, while the trz chemistry of first-row transition metals remains poorly developed.…”

Section: Introductionmentioning

confidence: 99%

“…However, in the case of complex 5, a dihedral angle of 47.36 (14)°, closer to that determined for the previously reported complex 2 (46.92(9)°), 21 was observed. These results show that the chelating bonding mode is more preferred when bulkier trz ligands are present (2:3 for R = p-tolyl vs 1:0 for R = mesityl) However, when the Ag-transmetalation route was applied for the coordination of L2a, L2b, and L2f, the air stable yellow monometallic Mn(I) tricarbonyl complexes containing chelating ditriazolylidene ligands fac-[Mn(di-trz R )(CO)3Br] [R = Me (8), Et (9), and Mes (10)] were, in all cases, isolated as the only product (Scheme 4). The identity of complexes 8-10 was determined by spectroscopic techniques and elemental analysis.…”

Section: Introductionmentioning

confidence: 99%

Manganese complexes with chelating and bridging di-triazolylidene ligands: synthesis and reactivity

et al. 2021

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“…In contrast, emission with comparably fast relaxation rates is usually ascribed to fluorescence. While fluorescent Pt II complexes with lifetimes in the nanosecond range have been reported in the literature, either they contain ligands that are fluorescent on their own ( e.g ., dyes, markers) − or the photoluminescence is ligand-centered. − Thus, the emission properties of proligand H 6 L(PF 6 ) 4 were also measured in the solid state, exhibiting weak photoluminescence in the same range as Pt 2 L(PF 6 ) 2 (λ em = 434 nm, λ ex = 311 nm) with a comparably short mean emission lifetime (τ av = 1.4 ns). This hints toward a similar situation as reported for fluorescent Pt II –NHC complexes.…”

Section: Resultsmentioning

confidence: 99%

Bimetallic Platinum Group Complexes of a Macrocyclic Pyrazolate/NHC Hybrid Ligand

Pickl

Pöthig

2021

Organometallics

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We present the synthesis, structural characterization, and photophysical properties of dinuclear Pd II and Pt II − NHC complexes Pd 2 L(PF 6 ) 2 and Pt 2 L(PF 6 ) 2 based on a macrocyclic calix[4]imidazolylidene[2]pyrazolate ligand obtained by in situ deprotonation of the tetraimidazolium salt H 6 L(PF 6 ) 4 . The Pt II congener was also prepared by transmetalation from previously published Ag I pillarplex Ag 8 L 2 (PF 6 ) 4 . NMR spectroscopy ( 1 H, 13 C, 195 Pt) combined with SC-XRD studies elucidated the structure of the Pd II and Pt II complexes in the solid state and in solution. The d 8 metal ions of both congeners are coordinated in a slightly distorted square-planar arrangement. Similar to the previously reported Ni II complex Ni 2 L(PF 6 ) 2 , the heavier metal homologues adopt a bent, saddle-shaped structure. As observed for structurally similar Pt II complexes in solution, bimetallic Pt 2 L(PF 6 ) 2 showed photoluminescence in the blue region. In the solid state, emission was observed at a similar energy with unusually short lifetimes compared to other monometallic Pt II complexes. DFT and TDDFT studies shed light on the nature of the most bathochromic transitions, suggesting a significant pyrazolate-and NHCcentered π−π* character.

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Fluorescent palladium(ii) and platinum(ii) NHC/1,2,3-triazole complexes: antiproliferative activity and selectivity against cancer cells

Abstract: Fluorescent Pd(ii) and Pt(ii) complexes with anti-proliferative activity bearing 4-methylene-7-methoxycoumarin (MMC) and 2,6-diispropylphenyl (Dipp) substituted NHC/1,2,3-triazole hybrid ligands are described.

Cited by 11 publications

References 51 publications

Luminescence and Palladium: The Odd Couple

Luminescence and Palladium: The Odd Couple

Manganese complexes with chelating and bridging di-triazolylidene ligands: synthesis and reactivity

Bimetallic Platinum Group Complexes of a Macrocyclic Pyrazolate/NHC Hybrid Ligand

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