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Exploring the Transphobia Effect on Heteroleptic NHC Cycloplatinated Complexes
Sara Fuertes, Andrés J. Chueca, and Violeta Sicilia
Inorg. Chem. 2015, 54, 9885-9895
DOI: 10.1021/acs.inorgchem.5b01655

The synthesis of 1-(4-cyanophenyl)-1H-imidazol (1) has been carried out by an improved method. Then its corresponding imidazolium iodide salt, 2, has been used to prepare the N-heterocyclic carbene (NHC) cycloplatinated compound [{Pt(μ-Cl)(C^C*)}2] (4) (HC^C*-κC* = 1-(4-cyanophenyl)-3-methyl-1H-imidazol-2-ylidene) following a step-by-step protocol. The intermediate complex [PtCl(κ3-2-Me-C3H4) (HC^C*-κC*)] (3) has also been isolated and characterized. Using 4 as precursor, several heteroleptic complexes of stoicheometry [PtCl(C^C*)L] (L = PPh3 (5), pyridine (py, 6), 2,6-dimethylphenyl isocyanide (CNXyl, 7), and 2-mercapto-1-methylimidazole (MMI, 8)) and [Pt(C^C*)LLκ]PF6 (L = PPh3, Lκ = py (9), CNXyl (10), and MMI (11)) have been synthesized. Complexes 6-8 were obtained as a mixture of cis- and trans-(C*,L) isomers, while trans-(C*,L) isomer was the only one observed for complexes 5 and 9-11. Their geometries have been discussed in terms of the degree of transphobia (T) of pairs of trans ligands and supported by theoretical calculations. The trans influence of the two κ Pt-C bonds present in these molecules, Pt-CAr and Pt-C*(NHC), has been compared from the JPt-P values observed in the new complex [Pt(C^C*)(dppe)]PF6 (dppe = 1, 2-bis(diphenylphosphino)ethane, 12)

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