Synthesis and Study of Calix[6]cryptamides: A New Class of Heteroditopic Receptors that Display Versatile Host–Guest Properties Toward Neutral Species and Organic Associated Ion‐Pair Salts
Identifieur interne : 000D91 ( Main/Exploration ); précédent : 000D90; suivant : 000D92Synthesis and Study of Calix[6]cryptamides: A New Class of Heteroditopic Receptors that Display Versatile Host–Guest Properties Toward Neutral Species and Organic Associated Ion‐Pair Salts
Auteurs : Stéphane Le Ac [France] ; Ivan Jabin [Belgique]Source :
- Chemistry – A European Journal [ 0947-6539 ] ; 2008-01-07.
English descriptors
Abstract
The synthesis of a new family of molecular receptors, namely the calix[6]cryptamides, was achieved through an original [1+1] macrocyclization step that consists of a peptide‐coupling reaction between tripodal triscarboxylic acids and a calix[6]trisamine subunit. Several C3‐ or C3v‐symmetrical calix[6]arene‐based compounds capped by a trisamido cryptand unit on the narrow rim have been obtained, with the more flexible partners leading to the best yields. These calix[6]cryptamides exhibit two favorably positioned binding sites for the complexation of organic‐associated ion pairs in close proximity: a well‐defined calix[6]arene cavity suitable for the inclusion of ammonium ions and a cryptamide unit for the coordination of anions. We demonstrate one example, chiral calix[6]cryptamide 12, that constitutes a heteroditopic receptor capable of cooperatively binding both a primary ammonium ion and its chloride counterion, thanks to a combination of polarization and induced‐fit effects. In addition, the hydrophobic calixarene cavity of 12 can strongly bind neutral guests through hydrogen bonding and is capable of discriminating between different enantiomers. All these versatile host–guest properties differ greatly from those observed in the parent calix[6]azacryptands.
Url:
DOI: 10.1002/chem.200701051
Affiliations:
- Belgique, France
- Haute-Normandie, Région Normandie, Région de Bruxelles-Capitale
- Bruxelles, Le Havre
- Université du Havre, Université libre de Bruxelles
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Several C3‐ or C3v‐symmetrical calix[6]arene‐based compounds capped by a trisamido cryptand unit on the narrow rim have been obtained, with the more flexible partners leading to the best yields. These calix[6]cryptamides exhibit two favorably positioned binding sites for the complexation of organic‐associated ion pairs in close proximity: a well‐defined calix[6]arene cavity suitable for the inclusion of ammonium ions and a cryptamide unit for the coordination of anions. We demonstrate one example, chiral calix[6]cryptamide 12, that constitutes a heteroditopic receptor capable of cooperatively binding both a primary ammonium ion and its chloride counterion, thanks to a combination of polarization and induced‐fit effects. In addition, the hydrophobic calixarene cavity of 12 can strongly bind neutral guests through hydrogen bonding and is capable of discriminating between different enantiomers. 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