Electron-Induced Inversion of Helical Chirality in Copper Complexes of N,N-Dialkylmethionines

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Science  26 May 2000:
Vol. 288, Issue 5470, pp. 1404-1407
DOI: 10.1126/science.288.5470.1404

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Stereodynamic complexes of copper were found to undergo inversion of a helical chiral element upon oxidation or reduction. The amino acid methionine was derivatized by the attachment of two chromophores to the nitrogen atom. The resultant ligands formed stable complexes with CuI and CuII salts. For a derivative of a given absolute chirality, the complexes afford nearly mirror image circular dichroism spectra. The spectral changes originate from reorientation of the nitrogen-attached chromophores due to a conformation interconversion driven by the exchange of a carboxylate for a sulfide ligand. The electrically induced chirality inversion coupled with strong interactions with polarized light is unique and may lead to novel chiral molecular devices.

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