Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 126, Issue 37, Pages 11711-11717Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja046633l
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Three chiral N-methylfulleropyrrolidine bisadducts were prepared, isolated, and completely resolved into each enantiomer using a chiral HPLC column, which were then converted to the corresponding optically active, cationic C-60-bisadducts to investigate if they could act as a macromolecular helicity inducer in a poly(phenylacetylene) bearing an anionic monoethyl phosphonate pendant (poly-1) in aqueous solution. Upon complexation with the chiral C-60-bisadducts, only the trans-3 bisadduct exhibited the characteristic induced circular dichroism (ICD) in the UV-visible region of the polymer backbone in dimethyl sulfoxide-water mixtures due to the predominantly one-handed helix formation of poly-1, while the trans-2 and cis-3 bisadducts induced almost no apparent CID in the same region. These results indicate that the helicity induction on poly-1 is highly sensitive to the structure and geometry of the cationic C-60-bisadducts with a different distance between the separated charges.
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