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; Francois Diederich

doi:https://doi.org/10.1002/chem.201404941

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, Francois Diederich

Department of Molecular Chemistry and Materials Science

Weizmann Institute Of Science

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	16070-16073
Number of pages	4
Journal	Chemistry-A European Journal
Volume	20
Issue number	49
DOIs	https://doi.org/10.1002/chem.201404941
State	Published - Dec 2014

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@article{634bec8f61564a9e8d2790b11cf41207,

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.",

author = "Tzirakis, {Manolis D.} and Alberti, {Mariza N.} and Haim Weissman and Boris Rybtchinski and Francois Diederich",

note = "ERC [246637]This work was supported by the ERC Advanced Grant No. 246637 ({"}OPTELOMAC'').",

year = "2014",

month = dec,

doi = "https://doi.org/10.1002/chem.201404941",

language = "الإنجليزيّة",

volume = "20",

pages = "16070--16073",

journal = "Chemistry-A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "49",

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TY - JOUR

T1 - Enantiopure Laterally Functionalized Alleno-Acetylenic Macrocycles

T2 - Synthesis, Chiroptical Properties, and Self-Assembly in Aqueous Media

AU - Tzirakis, Manolis D.

AU - Alberti, Mariza N.

AU - Weissman, Haim

AU - Rybtchinski, Boris

AU - Diederich, Francois

N1 - ERC [246637]This work was supported by the ERC Advanced Grant No. 246637 ("OPTELOMAC'').

PY - 2014/12

Y1 - 2014/12

N2 - 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.

AB - 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.

U2 - https://doi.org/10.1002/chem.201404941

DO - https://doi.org/10.1002/chem.201404941

M3 - مقالة

SN - 0947-6539

VL - 20

SP - 16070

EP - 16073

JO - Chemistry-A European Journal

JF - Chemistry-A European Journal

IS - 49

ER -

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

Abstract

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