Synthesis, characterization, structure and properties of copper and palladium complexes incorporating azo-amide ligands

Pattanayak, Poulami; Pratihar, Jahar Lal; Patra, Debprasad; Brandão, Paula; Félix, Vítor; Chattopadhyay, Surajit

doi:10.1016/j.poly.2014.03.053

Cited by 21 publications

(2 citation statements)

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“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] Several chemical properties of copper complexes have been attributed to easy accessibility to Cu(I), Cu(II) and Cu(III) oxidation states. 3,[20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38] Although a few studies on the coordination chemistry of copper using several kinds azo ligands have been reported 3,[39][40][41][42][43][44][45] but azo ligands have never been used for the synthesis of copper complexes targeting the oxidase models. The necessity to make progress in developing copper oxidase models requires synthesis of appropriate copper complexes to rationalize the functions of such oxidases unequivocally.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and structure of copper(II) complexes: Potential cyanide sensor and oxidase model

et al. 2016

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The new complexes of compositions [(L a) 2 Cu] and [(L b) 2 Cu] were prepared by treating with 2-hydroxy-5-methyl-3-(2-aryldiazenyl)phenylimino) methyl) benzaldehyde (HL a) and ethyl-2-cyano-3-(2hydroxy-5-methyl-3-(-(2-aryldiazenyl) phenylimino) methyl) phenyl) acrylate (HL b) ligands [where aryl is phenyl for HL 1 a and HL 1 b ; p-methyl phenyl for HL 2 a and HL 2 b ; and p-chloro phenyl for HL 3 a and HL 3 b ] with Cu(OAc) 2 .H 2 O, respectively. Both the bis copper(II) complexes consist of tridentate (N,N,O) anionic ligands, L − a or L − b. X-ray structures of the representative complexes [(L 1 a) 2 Cu] and [(L 2 b) 2 Cu] were determined to confirm the molecular species unequivocally. The molecular structure of copper complexes exhibited tetragonally distorted (Jahn-Teller) geometry consistent with the d 9 configuration of Cu(II) metal ion. Oxidation of benzyl alcohols using the newly synthesized complexes as catalyst has been studied. Photoluminescence properties of [(L 2 a) 2 Cu] and [(L 2 b) 2 Cu] were exploited for selective cyanide recognition. The [(L b) 2 Cu], complexes displayed antibacterial activity toward gram positive and gram negative bacteria.

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Section: Introductionmentioning

confidence: 99%

Synthesis and structure of copper(II) complexes: Potential cyanide sensor and oxidase model

et al. 2016

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“…Therefore, it is essential to investigate the relationship between their structure and photophysical properties so that their utilization as optical devices could be fulfilled. Apart from that, the pincer types of complexes have shown great promise as catalyst for the Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions [18,22,23]. These reactions enable us to have direct carbon-carbon bond formation in the aromatic system under mild conditions.…”

Section: Scheme 1 Different Canonical Structures Of Free and Bound Ligandmentioning

confidence: 99%

Synthesis, Photophysical Properties and Catalytic Activity of Ƙ3-SCS Pincer Palladium (II) Complex of N,N'-Di-Tert-Butylbenzene-1,3-Dicarbothioamide Supported by DFT Analysis

Das¹,

Kannan²,

Kumar³

et al. 2021

Preprint

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The title complex [PdCl(L)] (1), is obtained from the reaction of SCS pincer ligand HL (where, HL = N,N'-di-tert-butylbenzene-1,3-dicarbothioamide) with lithium tetrachloropalladate (II) in methanol. The compound 1 is characterized by elemental analysis, FTIR, 1H, and 13C-NMR spectroscopy, UV-Vis spectroscopy, powder X-ray diffraction and X-ray crystallographic techniques. At room temperature, 1 emits luminescence light of wavelength 460 nm in the solid state upon excitation by UV light of wavelength 280 nm. The average emission lifetime indicates that, both the ligand and complex emission is fluorescence in nature and involves mainly ligand centers π-π* deexcitation. It also shows good catalytic activity towards Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions of aryl bromides with tert-butyl acrylate and p-tolylboronic acid respectively. For both type of reactions, more than 99% conversion of the substrates is found to occur for electronically activated p-nitro bromobenzene using 1 mol % of 1. Further, modern DFT calculations are performed to decipher the mechanistic insight on the preferable pathways of the Mizoroki-Heck cross-coupling reaction. Stepwise free energy of reactions for various probable reaction pathways suggest that the catalytic route has profound preference for Pd(0)-Pd(II) over Pd(II)-Pd(IV) pathway.<br>

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Design of pincer complexes based on (methylsulfanyl)acetic/propionic acid amides with ancillary S‐ and N‐donors as potential catalysts and cytotoxic agents

Churusova

Aleksanyan

Васильев

et al. 2018

Applied Organom Chemis

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Pincer complexes featuring readily tunable tridentate ligand frameworks comprise one of the most actively studied classes of organometallic and metalorganic compounds and find extensive use in catalysis, organic synthesis, materials science, and other fields of chemistry and allied disciplines. Currently growing attention is devoted to non-classical ligand scaffolds, such as functionalized carboxamides, which offer multiple options for directed structural modifications. In this study, the reactions of (methylsulfanyl)acetyl and propanoyl chlorides with 2-(aminomethyl)pyridine, 2-(2-aminoethyl)pyridine, 8aminoquinoline and 2-(diphenylthiophosphoryl)aniline afford a series of new pincer-type ligands based on functionalized carboxamides. The ligands obtained readily undergo direct cyclopalladation under the action of PdCl 2 (NCPh) 2 in dichloromethane at room temperature, resulting in Pd(II) pincer complexes with N,N,S-and S,N,S-donor sets. Importantly, some of the cyclopalladated derivatives can also be produced efficiently under solvent-free conditions according to the approach recently developed by our group. The complexes obtained have been tested for cytotoxicity against several human cancer cell lines and catalytic activity in the model Suzuki reaction. The results have been compared to those for the related Pd(II) pincer complexes to define the main structure-activity relationships and to outline the most promising structures for further investigations. Yield: 87 mg (95%). M.p. > 225°C (dec.). 1 H NMR (400.13 MHz, CDCl 3 , δ, ppm): 2.73 (ddd, 1H, CH 2 , 2 J HH = 1.9 Hz, 3 J HH = 16.8 Hz, 3 J HH = 7.3 Hz), 3.15 (ddd, 1H, CH 2 S(O), 2 J HH = 2.2 Hz, 3 J HH = 16.8 Hz, 3 J HH = 11.4 Hz), 3.36 (ddd, 1H, CH 2 , 2 J HH = 1.9 Hz, 3 J HH = 13.0 Hz, 3 J HH = 11.4 Hz), 3.47 (ddd, 1H, CH 2 S(O), 2 J HH = 2.2 Hz, 3 J HH = 13.0 Hz, 3 J HH = 7.3 Hz), 3.51 (s, 3H, Me), 5.03 and 5.22 (ABq, 2H, CH 2 Py, J AB = 20.3 Hz), 7.35-7.39 (m, 1H, H(C4)), 7.48 (d, 1H, H(C2), 3 J HH = 7.9 Hz), 7.91 (dt, 1H, H(C3), 3 J HH = 7.9 Hz, 4 J HH = 1.6 Hz), 9.05 (d, 1H, H(C5), 3 J HH = 5.4 Hz).13

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Synthesis, characterization, structure and properties of copper and palladium complexes incorporating azo-amide ligands

Cited by 21 publications

References 51 publications

Synthesis and structure of copper(II) complexes: Potential cyanide sensor and oxidase model

Synthesis and structure of copper(II) complexes: Potential cyanide sensor and oxidase model

Synthesis, Photophysical Properties and Catalytic Activity of Ƙ3-SCS Pincer Palladium (II) Complex of N,N'-Di-Tert-Butylbenzene-1,3-Dicarbothioamide Supported by DFT Analysis

Design of pincer complexes based on (methylsulfanyl)acetic/propionic acid amides with ancillary S‐ and N‐donors as potential catalysts and cytotoxic agents

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