Enantiopure laterally functionalized alleno-acetylenic macrocycles: Synthesis, chiroptical properties, and self-assembly in aqueous media

Manolis D. Tzirakis, Mariza N. Alberti, Haim Weissman, Boris Rybtchinski, François Diederich

Research output: Contribution to journalArticle

6 Citations (Scopus)

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 selfassembly 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.

Original languageEnglish
Pages (from-to)16070-16073
Number of pages4
JournalChemistry - A European Journal
Volume20
Issue number49
DOIs
Publication statusPublished - Jan 12 2014

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Keywords

  • Alleno-acetylenes
  • Chiral macrocycles
  • Electronic circular dichroism
  • Scanning probe microscopy
  • Self-assembly

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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