Journal
TETRAHEDRON-ASYMMETRY
Volume 13, Issue 10, Pages 1043-1052Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0957-4166(02)00249-5
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Diastereomeric triamines containing two helicene moieties, 1,12-dimethylbenzo[c]phenanthrene, were synthesized and found to form folded structures in the water. Such folding was not observed for an achiral compound possessing a naphthalene moiety. The (M,M)-dihelicenetriamine with matching configuration at the helicene moieties formed a more stable folded structure than the (P,M)-isomer containing two enantiomeric helicene groups. The most stable folded conformation was predicted by the Monte Carlo method with Amber force field of the dihelicenetriamine. (C) 2002 Elsevier Science Ltd. All rights reserved.
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