title: Enantiopure laterally functionalized alleno-acetylenic macrocycles: synthesis, chiroptical properties, and self-assembly in aqueous media.
abstract: A family of shape-persistent alleno-acetylenic macrocycles (SPAAMs), peripherally decorated with structurally diverse pendant groups, has been synthesized and characterized in enantiomerically pure form. Their electronic circular dichroism (ECD) spectra feature a strong chiroptical response, which is more than two times higher than for open-chain tetrameric analogues. A water-soluble oligo(ethylene glycol)-appended SPAAM undergoes self-assembly in aqueous solution. Morphology studies by cryogenic transmission electron microscopy (cryo-TEM) revealed the formation of aggregates with fibrous fine structures that correspond to tubular, macrocyclic stacks.
authors.affiliation: Laboratorium für Organische Chemie, ETH Zurich, Vladimir-Prelog-Weg 3, 8093 Zurich (Switzerland), Fax: (+41) 44-632-1109.
authors.forename: Manolis D
authors.initials: MD
authors.lastname: Tzirakis
authors.forename: Mariza N
authors.initials: MN
authors.lastname: Alberti
authors.forename: Haim
authors.initials: H
authors.lastname: Weissman
authors.forename: Boris
authors.initials: B
authors.lastname: Rybtchinski
authors.forename: François
authors.initials: F
authors.lastname: Diederich
keywords: alleno-acetylenes; chiral macrocycles; electronic circular dichroism; scanning probe microscopy; self-assembly