Axially chiral facial amphiphiles with a dihydronaphthopentaphene structure as molecular tweezers for SWNTs.
Fiche publication
Date publication
octobre 2009
Auteurs
Membres identifiés du Cancéropôle Est :
Dr WAGNER Alain
Tous les auteurs :
Marquis R, Kulikiewicz K, Lebedkin S, Kappes MM, Mioskowski C, Meunier S, Wagner A
Lien Pubmed
Résumé
Syntheses of chiral 6,15-dihydronaphtho[2,3-c]pentaphene derivatives of opposite configurations are reported. Starting from anthracene, the strategy involves two key steps: a Diels-Alder reaction on a prochiral dianthraquinone, and an enantiomeric resolution using (-)-menthol. The final molecules exhibit very strong optical activity, as shown by their circular dichroism spectra, and are examples of chiral facial amphiphiles. Their adsorption at the surface of single-walled carbon nanotubes (SWNTs) has also been studied, and has been found to occur preferentially on 0.8-1.0 nm diameter nanotubes among the population of a high-pressure CO conversion (HiPco) SWNT sample (0.8-1.2 nm). The synthesised facial amphiphiles act as nano-tweezers for the diameter-selective solubilisation of SWNTs in water. The expected optical activities of the SWNT samples solubilised by each of the chiral amphiphiles have been studied by circular dichroism spectroscopy, but the results are not yet conclusive.
Référence
Chemistry. 2009 Oct 26;15(42):11187-96.