Synthesis, characterization, and cyclometalation studies of benzo[1,2-h: 5,4-h′]diquinolines with palladium and platinum

Young, Kenneth J. H.; Bu, Xianhui; Kaska, William C.

doi:10.1016/j.jorganchem.2011.08.012

Cited by 7 publications

(8 citation statements)

References 31 publications

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“…The protoligands Hnaphen, Hthnaphen, and Hbdq were reacted with K 2 [PtCl 4 ] in order to obtain the cyclometalated complexes in good to excellent yields [Pt(naphen)(Cl)] ( 1a ) (78%), [Pt(thnaphen)(Cl)] ( 2a ) (93%), and [Pt(bdq)(Cl)] ( 3 ) (57%). The analytical data of 3 were obtained as previously reported [ 47 ]. The Pt−Cl complexes 1a and 2a were then converted to the Pt−C≡CPh complexes [Pt(naphen)(C≡CPh)] ( 1b ) (99%) and [Pt(thnaphen)(C≡CPh)] ( 2b ) (90%) in excellent yields.…”

Section: Resultsmentioning

confidence: 99%

“…On the other hand, the condensation of the three aromatic rings in the C^N^C system dba 2− (H 2 dba = dibenzo[ c,h ]acridine) ( Scheme 1 A) has led to markedly increased photoluminescence quantum yields ( Φ L ) for the complex [Pt(dba)(DMSO)] compared with the derivatives [Pt(dppy)(dmso)] [ 37 ]. The corresponding N^C^N derivative [Pt(bdq)(Cl)] (Hbdq = benzo[1,2- h :5,4- h’ ]diquinoline ( Scheme 1 B) was previously synthesised, but its luminescence properties had not been studied yet [ 47 ].…”

Section: Introductionmentioning

confidence: 99%

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Photophysical Study on the Rigid Pt(II) Complex [Pt(naphen)(Cl)] (Hnaphen = Naphtho[1,2-b][1,10]Phenanthroline and Derivatives

et al. 2022

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The electrochemistry and photophysics of the Pt(II) complexes [Pt(naphen)(X)] (Hnaphen = naphtho[1,2-b][1,10]phenanthroline, X = Cl or C≡CPh) containing the rigid tridentate C^N^N-coordinating pericyclic naphen ligand was studied alongside the complexes of the tetrahydro-derivative [Pt(thnaphen)(X)] (Hthnaphen = 5,6,8,9-tetrahydro-naphtho[1,2-b][1,10]phenanthroline) and the N^C^N-coordinated complex [Pt(bdq)(Cl)] (Hbdq = benzo[1,2-h:5,4-h’]diquinoline. The cyclic voltammetry showed reversible reductions for the C^N^N complexes, with markedly fewer negative potentials (around −1.6 V vs. ferrocene) for the complexes containing the naphen ligand compared with the thnaphen derivatives (around −1.9 V). With irreversible oxidations at around +0.3 V for all of the complexes, the naphen made a difference in the electrochemical gap of about 0.3 eV (1.9 vs. 2.2 eV) compared with thnaphen. The bdq complex was completely different, with an irreversible reduction at around −2 V caused by the N^C^N coordination pattern, which lacked a good electron acceptor such as the phenanthroline unit in the C^N^N ligand naphen. Long-wavelength UV-Vis absorption bands were found around 520 to 530 nm for the C^N^N complexes with the C≡CPh coligand and were red-shifted when compared with the Cl derivatives. The N^C^N-coordinated bdq complex was markedly blue-shifted (493 nm). The steady-state photoluminescence spectra showed poorly structured emission bands peaking at around 630 nm for the two naphen complexes and 570 nm for the thnaphen derivatives. The bdq complex showed a pronounced vibrational structure and an emission maximum at 586 nm. Assuming mixed 3LC/3MLCT excited states, the vibronic progression for the N^C^N bdq complex indicated a higher LC character than assumed for the C^N^N-coordinated naphen and thnaphen complexes. The blue-shift was a result of the different N^C^N vs. C^N^N coordination. The photoluminescence lifetimes and quantum yields ΦL massively increased from solutions at 298 K (0.06 to 0.24) to glassy frozen matrices at 77 K (0.80 to 0.95). The nanosecond time-resolved study on [Pt(naphen)(Cl)] showed a phosphorescence emission signal originating from the mixed 3LC/3MLCT with an emission lifetime of around 3 µs.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Photophysical Study on the Rigid Pt(II) Complex [Pt(naphen)(Cl)] (Hnaphen = Naphtho[1,2-b][1,10]Phenanthroline and Derivatives

et al. 2022

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“…Among the general category of PCP, NCN or NN ' N pincers, only a few of them have idealized molecular point group symmetry lower than C 2 (Figure 7). [42][43][44][45] Indeed, the achiral pincer ligands typically have higher molecular symmetry (Figure 8). [42][43][44][45] 48 and as a portion of this research project.…”

Section: -5-3-pincer Ligands With Low Molecular Symmetrymentioning

confidence: 99%

Group 11 Pincer Oxazoline Complexes

Seighalani¹

2021

Preprint

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The synthesis and characterization of new copper pincer complexes via cyclometallation of potentially anionic pincer ligands with C1 point group symmetry is reported. All of these complexes have been characterized by single crystal X-ray diffraction method, which confirms the proposed tridentate binding mode of pincer ligand and the formation of an amido N-Cu bond. The reactivity of two of the complexes was investigated towards C-C bond formation reaction, notably the Henry reaction. One of the complexes, which was derived from the achiral pincer ligand, is shown to be a suitable catalyst for the Henry reaction under the standard conditions. The Henry or nitroaldol reaction is one of the organic reactions which affords a C-C bond. The product of this reaction is a β-nitro alcohol which is formed by addition of a nitroalkane to a carbonyl compound.

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“…For background to pincer palladium complexes, see: van Koten & Gebbink (2011); Moreno et al (2010); Selander & Szabó (2011). For palladium complexes with NCN pincer ligands, see: Hao et al (2010); Young et al (2011). For studies on the chemistry of bis(oxazole) pincer palladium complexes, see: Luo et al (2007Luo et al ( , 2011; Xu et al (2011).…”

Section: Related Literaturementioning

confidence: 99%

“…Considerable attention has recently been devoted to pincer-Pd complexes due to their catalytic abilities (Ghorai et al, 2012;van Koten & Gebbink, 2011;Moreno et al, 2010;Selander & Szabó, 2011). We are interested in the NCN type of pincer-Pd complexes (Luo et al, 2007(Luo et al, , 2011(Luo et al, , 2012Xu et al, 2011) as a variety of nonphosphine pincer catalytic system, that contains two nitrogen atoms as donating sites in the coordination sphere (Hao et al, 2010;Young et al, 2011) The title compound was conveniently synthesized from the reaction of Pd(dba) 2 (dba = dibenzylideneacetone) with 1bromo-2,6-bis(5-ethoxyoxazol-2-yl)-4-methoxy benzene in dry benzene under reflux in an argon atmosphere. As a result, the title compound was isolated with 84% yield.…”

Section: S1 Commentmentioning

confidence: 99%

[2,6-Bis(5-ethoxy-1,3-oxazol-2-yl)-4-methoxyphenyl-κ³N,C¹,N′]bromidopalladium(II)

Nan¹,

Tan²,

Luo³

2012

Acta Cryst E

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In the title compound, [PdBr(C17H17N2O5)], the PdII atom is coordinated by an N,C 1,N′-tridentate pincer ligand and a Br atom in a distorted square-planar geometry. In the crystal, molecules are connected by C—H⋯Br and C—H⋯O hydrogen bonds, and π–π interactions between the oxazole and benzene rings [centroid–centroid distance = 3.7344 (19) Å], resulting in a three-dimensional supramolecular structure.

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Synthesis, characterization, and cyclometalation studies of benzo[1,2-h: 5,4-h′]diquinolines with palladium and platinum

Cited by 7 publications

References 31 publications

Photophysical Study on the Rigid Pt(II) Complex [Pt(naphen)(Cl)] (Hnaphen = Naphtho[1,2-b][1,10]Phenanthroline and Derivatives

Photophysical Study on the Rigid Pt(II) Complex [Pt(naphen)(Cl)] (Hnaphen = Naphtho[1,2-b][1,10]Phenanthroline and Derivatives

Group 11 Pincer Oxazoline Complexes

[2,6-Bis(5-ethoxy-1,3-oxazol-2-yl)-4-methoxyphenyl-κ³N,C¹,N′]bromidopalladium(II)

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Synthesis, characterization, and cyclometalation studies of benzo[1,2-h: 5,4-h′]diquinolines with palladium and platinum

Cited by 7 publications

References 31 publications

Photophysical Study on the Rigid Pt(II) Complex [Pt(naphen)(Cl)] (Hnaphen = Naphtho[1,2-b][1,10]Phenanthroline and Derivatives

Photophysical Study on the Rigid Pt(II) Complex [Pt(naphen)(Cl)] (Hnaphen = Naphtho[1,2-b][1,10]Phenanthroline and Derivatives

Group 11 Pincer Oxazoline Complexes

[2,6-Bis(5-ethoxy-1,3-oxazol-2-yl)-4-methoxyphenyl-κ3N,C1,N′]bromidopalladium(II)

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[2,6-Bis(5-ethoxy-1,3-oxazol-2-yl)-4-methoxyphenyl-κ³N,C¹,N′]bromidopalladium(II)