Axially chiral facial amphiphiles with a dihydronaphthopentaphene structure as molecular tweezers for SWNTs.
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.
Marquis
Renaud
R
Laboratory of Functional Chemo-Systems, UMR 7199, Faculté de Pharmacie, Université de Strasbourg, 74 Route du Rhin, BP 24, 67401 Illkirch, France.
Kulikiewicz
Krystyna
K
Lebedkin
Sergei
S
Kappes
Manfred M
MM
Mioskowski
Charles
C
Meunier
Stéphane
S
Wagner
Alain
A
D000873:Anthracenes / Q000737:chemistry*; D002942:Circular Dichroism; D037742:Nanotubes, Carbon / Q000737:chemistry*; D013237:Stereoisomerism
C546738:6,15-dihydronaphtho(2,3-c)pentaphene; D000873:Anthracenes; D037742:Nanotubes, Carbon; C034020:anthracene