Extreme Complementarity in a Macrocycle−Tweezer Complex

Interaction of a novel pyrene-based tweezer molecule with a macrocyclic ether-imide-sulfone results in formation of a strongly bound complex (K a = 24 000 M-1) in which binding results not only from π−π stacking interactions involving pyrene units as donors and macrocyclic naphthalene-tetracarboximi...

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Bibliographic Details
Published inOrganic letters Vol. 5; no. 23; pp. 4353 - 4356
Main Authors Colquhoun, Howard M, Zhu, Zhixue, Williams, David J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 13.11.2003
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PI-ASSOCIATED CATENANES
CATENANES
RECOGNITION
ETHER
RING
GUEST
SWITCH
MOLECULAR TWEEZERS
RECEPTORS
PSEUDOROTAXANES
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Summary:Interaction of a novel pyrene-based tweezer molecule with a macrocyclic ether-imide-sulfone results in formation of a strongly bound complex (K a = 24 000 M-1) in which binding results not only from π−π stacking interactions involving pyrene units as donors and macrocyclic naphthalene-tetracarboximide and biphenylenedisulfone groups as acceptors but also from N−H···O and C−H···O hydrogen bonds and from “reverse” π-stacking of the electron-poor isophthaloyl residue of the tweezer with an electron-rich 3-aminophenoxy residue of the macrocyclic imide.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol035626j