Syntheses, structures, and solid-state phosphorescence characteristics of trans-bis(salicylaldiminato)Pt(II) complexes bearing perpendicular N-aryl functionalities

Iwata, Shotaro; Takahashi, Hidenori; Ihara, Asami; Hiramatsu, Kumiko; Adachi, Junya; Kawamorita, Soichiro; Komiya, Naruyoshi

doi:10.1007/s11243-017-0198-9

Cited by 3 publications

(2 citation statements)

References 56 publications

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“…However, these materials have not yet been studied sufficiently, owing to the deleterious effects of intermolecular interactions . As part of our program aimed at developing new functional materials based on square planar d 8 transition metal platforms bearing three‐dimensional (3D) superstructures, we are investigating the association/aggregation properties, and molecular mobilities[6c], of chiral clothespin‐shaped binuclear complexes comprising trans ‐bis(salicylaldiminato), and trans ‐bis(aminotroponato) Pd(II)[6a], [6c], [6d], [6e], , and Pt(II)[6b], [6d] complexes doubly linked with flexible or rigid carbon bridges. These clothespin‐shaped complexes exhibit various association and aggregation motifs due to the conformational variation arising from the opening and closing anisotropic flapping motions of the cofacial coordination blades.…”

Section: Introductionmentioning

confidence: 99%

Variations in the Solid‐State Emissions of Clothespin‐Shaped Binuclear trans‐Bis(salicylaldiminato)platinum(II) with Halogen Functionalities

Ikeshita

Ito

2019

Eur J Inorg Chem

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The syntheses, aggregation motifs and solid-state emissions of clothespin-shaped binuclear trans-bis(salicylaldiminato)platinum(II) complexes 1-4 bearing halogen atoms (X) at the para positions of phenoxy moieties are described and compared with those of the non-substituted analog 5. Crystalline (±)-4 (X = I, polymorph B) obtained by recrystallization from benzene exhibits intense phosphorescent emission under UV irradiation at ambient temperature, while crystals of (±)-1 (X = F), (±)-2 (X = Cl), (±)-3 (X = Br) and (±)-4 (X = I, polymorph A), obtained from poor solvents including hexanes, are less emissive under the same conditions. The emission intensities of these crystals increase in the order of (±)-4 (B) > (±)-5 > (±)-1- [a] 3562 platinum(II) complexes bearing halogen functionalities, with a focus on a mechanistic rationale for the specific emission enhancements observed.Scheme 2. Clothespin-shaped platinum(II) complexes 1-5 (R-form).

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Section: Introductionmentioning

confidence: 99%

Variations in the Solid‐State Emissions of Clothespin‐Shaped Binuclear trans‐Bis(salicylaldiminato)platinum(II) with Halogen Functionalities

Ikeshita

Ito

2019

Eur J Inorg Chem

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“…[11] In other cases, Pt(II) could coordinate with salicylaldiminato ligands in molecular ratio 1:2 to form transbis(salicylaldiminato)Pt(II) complexes in which trans-coordination and crystal packing of these complexes were established based on single-crystal X-ray diffraction data. [12,13] Chirality is usually an important factor in the field of pharmaceuticals, agrochemicals and cosmetics. Chirality is known to change the pharmacological behavior of metal complexes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and anticancer properties of platinum(II) complexes bearing chiral azomethine ligands

Trung,

Nam,

Van Tuyen

2021

Vietnam Journal of Chemistry

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Pt(II) complexes bearing one N‐salicylidene‐(S)‐1‐phenylethylamine [HL(S)] or N‐salicylidene‐(R)‐1‐phenylethylamine [HL(R)] were synthesized and characterized by electrospray ionization mass spectroscopy (ESI‐MS), Fourier‐transform infrared (FT‐IR), nuclear magnetic resonance (NMR) and circular dichroism (CD) spectroscopies. The results of the micro‐analytic and spectroscopic methods disclosed that the reaction of K2PtCl4 with the chiral azomethine ligand in DMSO produced both trans‐ and cis‐[Pt(II)L(DMSO)Cl]. Then only trans‐[Pt(II)L(DMSO)Cl] isomers in Na2CO3 solution can transform to Pt(II) complexes 3 in coordination of the ligands to platinum as tridentate C,N,O‐donors. The photophysical properties of obtained platinum(II) complexes were studied by UV‐visible and luminescent spectra. The results showed that they all exhibited emission in the visible region. Anticancer properties in vitro of obtained Pt(II) complexes were scaned for KB and HepG‐2 cancer cell lines. They had good activity for the tested cancer cells. The cis‐Pt(II) complexes possessed higher anticancer activity than trans‐Pt(II) complexes and R‐enantiomers were found to be more cytotoxic than S‐enantiomers.

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Heat‐Resistant Properties in the Phosphorescence of trans‐Bis[β‐(iminomethyl)aryloxy]platinum(II) Complexes: Effect of Aromaticity on d–π Conjugation Platforms

Inoue

Naito

Ehara

2019

Chemistry A European J

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The heat‐resistant properties towards thermal emission quenching of trans‐bis[(β‐iminomethyl)aryloxy]platinum(II) complexes bearing 3‐iminomethyl‐2‐naphtholato‐ (1), 1‐iminomethyl‐2‐naphtholato‐ (2), 2‐iminomethyl‐1‐naphtholato‐ (3), and 2‐iminomethyl‐1‐phenolato (4) moieties, and a mechanistic rationale of these properties, are described in this report. Complex 1 a, with N,N′‐dipentyl groups, exhibits intense red emission in 2‐methyl‐2,3,4,5‐tetrahydrofuran (2‐MeTHF) at 298 K, whereas the analogues 2 a–4 a are less or non‐emissive under the same measurement conditions. All four complexes are highly emissive at 77 K. The heat‐resistant properties toward thermal emission quenching (Φ298 K/Φ77 K) increase in the order 1 a (0.52)>2 a (0.09)>3 a (0.02)>>4 a (0.00). We investigated the emission decay and thermal‐deactivation processes using density functional theory (DFT), time‐dependent (TD) DFT, and double‐hybrid density functional theory (DHDF) calculations of N,N′‐diethyl forms 1 b–4 b, and discuss the results with a focus on the energy levels, molecular structures, and electronic configurations in the triplet excited states. The energy differences between the triplet metal–ligand charge transfer (3MLCT) state and minimum‐energy crossing point between the lowest triplet state and singlet ground state (MECP) increase in the order 1 a>2 a, 3 a>4 a, consistent with the experimental results for the heat‐resistant properties of these complexes. The origin of the present structure dependence of the 3MLCT–MECP energy gap is ascribed to the ease or difficulty of the high‐lying dσ* orbital participating in the MECP upon thermal structural distortion. The structure dependence in energy gaps between the π* and dσ* orbitals, which is key for facilitating the thermal deactivation process, is rationally correlated with the extent of aromaticity on the coordination platforms (1 b>(2 b, 3 b)>4 b).

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Syntheses, structures, and solid-state phosphorescence characteristics of trans-bis(salicylaldiminato)Pt(II) complexes bearing perpendicular N-aryl functionalities

Cited by 3 publications

References 56 publications

Variations in the Solid‐State Emissions of Clothespin‐Shaped Binuclear trans‐Bis(salicylaldiminato)platinum(II) with Halogen Functionalities

Variations in the Solid‐State Emissions of Clothespin‐Shaped Binuclear trans‐Bis(salicylaldiminato)platinum(II) with Halogen Functionalities

Synthesis, characterization and anticancer properties of platinum(II) complexes bearing chiral azomethine ligands

Heat‐Resistant Properties in the Phosphorescence of trans‐Bis[β‐(iminomethyl)aryloxy]platinum(II) Complexes: Effect of Aromaticity on d–π Conjugation Platforms

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