engleski

Bioorganometallic chemistry of 1, n´-disubstituted ferrocene oligoamides

Ferrocenes substituted with chiral amino acids at both cyclopentadienyl rings show very interesting supramolecular interactions between the two substituents.[1] These 1, n´-disubstituted ferrocenes have served as inspiration for selective catalysts and supramolecular systems.[2, 3] Recently we discovered that a formal isomerization of one amide bond can yield very selective supramolecular catalysts.[4] Herein, we present the synthesis and characterization of 1, n´-disubstituted ferrocenes bearing pedant trans-1S, 2S-cyclohexanediamines instead of amino acids (2). The corresponding mono-substituted analogues (1) have been prepared for comparison. In particular, all compounds have been studied using NMR, IR, UV-Vis and CD spectroscopy, as well as mass spectrometry. In addition, the structural features have also been elucidated from several determined x-ray single crystal structures and DFT calculations. It is interesting to mention that disubstituted derivative 2a reveals significantly different CD spectra in dichloromethane and methanol, Figure 1, indicating a major change in supramolecular organization in solution.

amino acids ; ferrocene ; supramolecular

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