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Open AccessArticle

Design of a Novel Class of N-Heterocyclic Carbene Cycloplatinated Complexes Containing Pyrene Chromophores

by Zeping Zhang, Yaping Cheng, Geoffrey Gontard, Tim Riesebeck, Sandy Fornal, Thomas Strassner and Hani Amouri

Molecules 2025, 30(22), 4473; https://doi.org/10.3390/molecules30224473 - 19 Nov 2025

Cited by 1 | Viewed by 829

Abstract

Cycloplatinated complexes incorporating pyrene chromophores of the formulae (C^C*)Pt(acac) (3, 4), (C^C* = Pyrenyl-NHC, acac = acetylacetonate) were prepared and fully characterized. For comparison, two regioisomeric complexes were prepared following synthetic procedures developed by us. One isomer has the Pt(II) center attached to the 2-position of the pyrene chromophore, while the other regioisomer has the metal center attached at the 1-position of the organic chromophore. The molecular structures of 3 and 4 were ascertained by X-ray diffraction, and they prove the identity of the targeted compounds. Both complexes are emissive at room temperature in the red part of the spectrum in poly(methyl methacrylate) (PMMA), as well as at 77 K in 2-methyltetrahydrofuran (2-MeTHF). The regioisomer containing the Pt(II) at the 1-position shows enhanced emissive properties compared to the other regioisomer. Full article

(This article belongs to the Special Issue Inorganic Chemistry in Europe 2025)

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15 pages, 3824 KB

Open AccessFeature PaperArticle

Photophysical Properties and Kinetic Studies of 2-Vinylpyridine-Based Cycloplatinated(II) Complexes Containing Various Phosphine Ligands

by Vahideh Dolatyari, Hamid R. Shahsavari, Sepideh Habibzadeh, Reza Babadi Aghakhanpour, Sareh Paziresh, Mohsen Golbon Haghighi and Mohammad Reza Halvagar

Molecules 2021, 26(7), 2034; https://doi.org/10.3390/molecules26072034 - 2 Apr 2021

Cited by 4 | Viewed by 3409

Abstract

A series of cycloplatinated(II) complexes with general formula of [PtMe(Vpy)(PR₃)], Vpy = 2-vinylpyridine and PR₃ = PPh₃ (1a); PPh₂Me (1b); PPhMe₂ (1c), were synthesized and characterized by means of spectroscopic methods. These cycloplatinated(II) complexes were luminescent at room temperature in the yellow–orange region’s structured bands. The PPhMe₂ derivative was the strongest emissive among the complexes, and the complex with PPh₃ was the weakest one. Similar to many luminescent cycloplatinated(II) complexes, the emission was mainly localized on the Vpy cyclometalated ligand as the main chromophoric moiety. The present cycloplatinated(II) complexes were oxidatively reacted with MeI to yield the corresponding cycloplatinated(IV) complexes. The kinetic studies of the reaction point out to an S_N2 mechanism. The complex with PPhMe₂ ligand exhibited the fastest oxidative addition reaction due to the most electron-rich Pt(II) center in its structure, whereas the PPh₃ derivative showed the slowest one. Interestingly, for the PPhMe₂ analog, the trans isomer was stable and could be isolated as both kinetic and thermodynamic product, while the other two underwent trans to cis isomerization. Full article

(This article belongs to the Special Issue Synthesis and Investigation of Novel Coordination Compounds)

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8 pages, 1239 KB

Open AccessArticle

Cleavage of the Pt-I bond in a Primary Cycloplatinated Amine by Chelation

by William Raven, Irmgard Kalf and Ulli Englert

Crystals 2015, 5(2), 244-251; https://doi.org/10.3390/cryst5020244 - 22 May 2015

Cited by 3 | Viewed by 4489

Abstract

In the square-planar cycloplatinated complex of R–phenylethylamine, both additional substituents, an anionic iodo and a neutral donor ligand, have been replaced by chelating ethylenediamine. A very pronounced trans influence is observed in the cationic product complex: Two significantly different bond distances to the chelating ligand are found, the longer in trans geometry to the coordinated carbon atom. The positive charge of the monocationic complex is balanced by an uncoordinated iodide. This target solid crystallizes with four independent cations and anions in the unit cell; pairs of complex cations related by pseudo-inversion are stabilized by T stacking. Classical N–H···I hydrogen bonds lead to a layer structure in the (0 1 0) plane. Full article

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29 pages, 1506 KB

Open AccessArticle

Experimental and Theoretical Studies of the Factors Affecting the Cycloplatination of the Chiral Ferrocenylaldimine (S_C)-[(η⁵-C₅H₅)Fe{(η⁵-C₅H₄)–C(H)=N–CH(Me)(C₆H₅)}]

by Concepción López, Ramón Bosque, Marta Pujol, Jonathan Simó, Eila Sevilla, Mercè Font-Bardía, Ramon Messeguer and Carme Calvis

Inorganics 2014, 2(4), 620-648; https://doi.org/10.3390/inorganics2040620 - 6 Nov 2014

Cited by 10 | Viewed by 7759

Abstract

The study of the reactivity of the enantiopure ferrocenyl Schiff base (S_C)-[FcCH=N–CH(Me)(C₆H₅)] (1) (Fc = (η⁵-C₅H₅)Fe(η⁵-C₅H₄)) with cis-[PtCl₂(dmso)₂ [...] Read more.

The study of the reactivity of the enantiopure ferrocenyl Schiff base (S_C)-[FcCH=N–CH(Me)(C₆H₅)] (1) (Fc = (η⁵-C₅H₅)Fe(η⁵-C₅H₄)) with cis-[PtCl₂(dmso)₂] under different experimental conditions is reported. Four different types of chiral Pt(II) have been isolated and characterized. One of them is the enantiomerically pure trans-(S_C)-[Pt{κ¹-N[FcCH=N–CH(Me)(C₆H₅)]}Cl₂(dmso)] (2a) in which the imine acts as a neutral N-donor ligand; while the other three are the cycloplatinated complexes: [Pt{κ²-C,N [(C₆H₄)–N=CHFc]}Cl(dmso)] (7a) and the two diastereomers {(S_p,S_C) and (R_p,S_C)} of [Pt{κ²-C,N[(η⁵-C₅H₃)–CH=N–{CH(Me)(C₆H₅)}]Fe(η⁵-C₅H₅)}Cl(dmso)] (8a and 9a, respectively). Isomers 7a-9a, differ in the nature of the metallated carbon atom [C^Ph (in 7a) or C^Fc (in 8a and 9a)] or the planar chirality of the 1,2-disubstituted ferrocenyl unit (8a and 9a). Reactions of 7a–9a with PPh₃ gave [Pt{κ²-C,N[(C₆H₄)–N=CHFc]}Cl(PPh₃)] (in 7b) and the diastereomers (S_p,S_C) and (R_p,S_C) of [Pt{κ²-C,N[(η⁵-C₅H₃)–CH=N–{CH(Me)(C₆H₅)}] Fe(η⁵-C₅H₅)}Cl(PPh₃)] (8b and 9b, respectively). Comparative studies of the electrochemical properties and cytotoxic activities on MCF7 and MDA-MB231 breast cancer cell lines of 2a and cycloplatinated complexes 7b-9b are also reported. Theoretical studies based on DFT calculations have also been carried out in order to rationalize the results obtained from the cycloplatination of 1, the stability of the Pt(II) complexes and their electrochemical properties. Full article

(This article belongs to the Special Issue Organoplatinum Complexes)

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17 pages, 631 KB

Open AccessReview

Diarylplatinum(II) Compounds as Versatile Metallating Agents in the Synthesis of Cyclometallated Platinum Compounds with N-Donor Ligands

by Margarita Crespo

Inorganics 2014, 2(1), 115-131; https://doi.org/10.3390/inorganics2010115 - 21 Mar 2014

Cited by 16 | Viewed by 9714

Abstract

This review deals with the reactions of diarylplatinum(II) complexes with N-donor ligands to produce a variety of cycloplatinated compounds including endo-five-, endo-seven-, endo-six- or exo-five-membered platinacycles. The observed reactions result from a series of oxidative addition/reductive elimination processes taking place at platinum(II)/platinum(IV) species and involving C–X (X = H, Cl, Br) bond activation, arene elimination, and, in some cases, C_aryl–C_aryl bond formation. Full article

(This article belongs to the Special Issue Organoplatinum Complexes)

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