Enantiopure Laterally-functionalized Alleno-Acetylenic Macrocycles: Synthesis, Chiroptical Properties and Self-Assembly in Aqueous Media

; ; ; ; (). Enantiopure Laterally-functionalized Alleno-Acetylenic Macrocycles: Synthesis, Chiroptical Properties and Self-Assembly in Aqueous Media. Chemistry - A European Journal 2014, 20 (49), 16070–16073. Peer reviewed.

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.

dx.doi.org/10.1002/chem.201404941