The study of the reactivity of the enantiopure ferrocenyl Schiff base (
SC)-[FcCH=N–CH(Me)(C
6H
5)] (
1) (Fc = (η
5-C
5H
5)Fe(η
5-C
5H
4)) with
cis-[PtCl
2(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-(
SC)-[Pt{κ
1-
N[FcCH=N–CH(Me)(C
6H
5)]}Cl
2(dmso)] (
2a) in which the imine acts as a neutral
N-donor ligand; while the other three are the cycloplatinated complexes: [Pt{κ
2-C,
N [(C
6H
4)–N=CHFc]}Cl(dmso)] (
7a) and the two diastereomers {
(Sp,
SC) and
(Rp,SC)} of [Pt{κ
2-C,
N[(η
5-C
5H
3)–CH=N–{CH(Me)(C
6H
5)}]Fe(η
5-C
5H
5)}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 PPh
3 gave [Pt{κ
2-C,
N[(C
6H
4)–N=CHFc]}Cl(PPh
3)] (in
7b) and the diastereomers
(Sp,
SC) and
(Rp,SC) of [Pt{κ
2-C,
N[(η
5-C
5H
3)–CH=N–{CH(Me)(C
6H
5)}] Fe(η
5-C
5H
5)}Cl(PPh
3)] (
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.
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