Palladium(II) complexes bearing <i>N</i>‐alkylpiperidoimidazolin‐2‐ylidene derivatives: Effect of alkyl chain length of ligands on catalytic activity

Çakır, Sinem Yeygel; Türkmen, Hayati

doi:10.1002/aoc.3969

Cited by 7 publications

(3 citation statements)

References 49 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A number of piperidoimidazolinium salts ( 1a ‐ d ) functioned with substituted water soluble group (sulfonate ( a ), esters ( b , c ) and carboxylic acid ( d )) were synthesized as reported in the literature (Scheme ) . All salts ( 1a‐d ) were obtained in the form of a yellow, ionic liquid and found to be soluble in DMSO, H 2 O and polar solvents.…”

Section: Resultsmentioning

confidence: 99%

“…Studies to develop catalytic systems that perform in a short time at room temperatures using low catalyst loading is an ongoing effort. Recently, we prepared Pd (II)‐piperidoimidazolin‐2‐ylidene complexes bearing alkyl, benzil and aryl group . The catalytic properties of these complexes were investigated in the different catalytic reactions.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of water soluble Pd‐Piperidoimidazolin‐2‐ylidene complexes and their catalytic activities in neat water

Çakır

Türkmen

2020

Applied Organom Chemis

Self Cite

View full text Add to dashboard Cite

Through the strategy of water soluble N‐heterocyclic carbene (NHC) ligand, Pd‐catalyzed reactions were developed in aqueous media. Therefore, four new piperidoimidazolinium salts (1a‐d) consisting of sulfonate (a), esther (b, c) and carboxylic acid (d) functionalities and their water‐soluble Pd‐NHC complexes (2a‐d) were synthesized. The new compounds were characterized by elemental analysis, FTIR, TGA, UV–vis and NMR spectroscopy. The catalytic activities of water soluble Pd‐NHC complexes (2a‐d) were investigated using the Suzuki‐Miyaura (S‐M) reaction and the reduction of nitroarenes. We found that the water‐soluble polar or ionic groups on piperidoimidazolin‐2‐ylidine had an effect on the catalytic activity. The water‐soluble catalyst can be recycled efficiently and reused six times with only a very slight loss of catalytic activity.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of water soluble Pd‐Piperidoimidazolin‐2‐ylidene complexes and their catalytic activities in neat water

Çakır

Türkmen

2020

Applied Organom Chemis

Self Cite

View full text Add to dashboard Cite

show abstract

“…In particular, only a few examples of complexes with cyclometalated NHCs are known [45–47] . The saturated derivative of the imidazo[1,5‐ a ]pyridine framework (Scheme 1) is known as a NHC motif for over a decade and can be found in iridium, palladium and rhodium complexes [48–58] . But to the best of our knowledge there are neither platinum nor cyclometalated complexes known with this motif.…”

Section: Introductionmentioning

confidence: 99%

Phosphorescent Cyclometalated Platinum(ii) Hexahydroimidazo[1,5‐a]pyridinylidene Complexes

Stipurin

Straßner

2022

Eur J Inorg Chem

View full text Add to dashboard Cite

The synthesis of N-heterocyclic carbene precursors based on the hexahydroimidazo[1,5-a]pyridine and their corresponding cyclometalated platinum(II) carbene complexes is reported. All compounds are fully characterized by standard techniques and additionally X-ray structures could be obtained for three complexes. The photophysical properties of these platinum complexes were investigated by absorption and photolumines-cence measurements. All complexes showed strong phosphorescence at room temperature in the sky-blue area with quantum yields of up to 71 %. Additionally, their electrochemical properties were examined by voltammetry experiments. All results were rationalized by quantum chemical DFT calculations (PBE0/6-311G*).

show abstract

Synthesis of Aryl‐Functionalized Benzo[d,e]Benzo[4,5]İmidazo[2,1‐a]Isoquinolin‐7‐One Derivatives: DNA Intercalation Causing Cytotoxicity

Türkmen,

Çakır,

Batıkan Kavukcu

et al. 2024

ChemistrySelect

Self Cite

View full text Add to dashboard Cite

This study focuses on the cytotoxic effect properties of 4‐aryl‐functionalized benzo[d,e]benzo[4,5]imidazo[2,1‐a]isoquinolin‐7‐one (4‐X−Ar−BBI). The electron‐withdrawing and electron‐donating substituents located at the para position of the phenyl ring attached to the heterocyclic structure have altered the pi electron density within the structure. This change in electron density has influenced the intercalation ability of the heterocyclic structure and has impacted the intensity of its interaction with DNA. The 4‐aryl‐benzo[d,e]benzo[4,5]imidazo[2,1‐a]isoquinolin‐7‐one derivatives (4‐X−Ar−BBI) were prepared via the Suzuki–Miyaura cross‐coupling reaction. The optimum reaction conditions were determined to be 70 °C for 5 hours using catalyst 1 and K2CO3, resulting in a yield of 96 % of 4‐H−Ar−BBI. Characterization of all compounds (4‐X−Ar−BBI) was performed using Fourier Transform Infrared spectroscopy, mass spectrometry, and 1H‐ and 19F‐NMR spectroscopies. The cytotoxic activities of the compounds (4‐X−Ar−BBI) were investigated against cancer cell lines, specifically HeLa (human cervix adenocarcinoma epithelial), PC3 (human prostate), and MCF‐7 (human breast). The stability of 4‐CN−Ar−BBI and the binding modes between 4‐CN−Ar−BBI and DNA were investigated via 1H‐NMR spectroscopy and UV‐Vis spectroscopy, respectively. 4‐CH3−3‐NO2−Ar−BBI exhibited the most potent cytotoxic activity against MCF‐7, and 4‐F−Ar−BBI showed the highest activity against HeLa, with IC50 values of 3.675 and 7.370 μM, respectively.

show abstract

Palladium(II) complexes bearing N‐alkylpiperidoimidazolin‐2‐ylidene derivatives: Effect of alkyl chain length of ligands on catalytic activity

Cited by 7 publications

References 49 publications

Synthesis of water soluble Pd‐Piperidoimidazolin‐2‐ylidene complexes and their catalytic activities in neat water

Synthesis of water soluble Pd‐Piperidoimidazolin‐2‐ylidene complexes and their catalytic activities in neat water

Phosphorescent Cyclometalated Platinum(ii) Hexahydroimidazo[1,5‐a]pyridinylidene Complexes

Synthesis of Aryl‐Functionalized Benzo[d,e]Benzo[4,5]İmidazo[2,1‐a]Isoquinolin‐7‐One Derivatives: DNA Intercalation Causing Cytotoxicity

Contact Info

Product

Resources

About