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 : 000F64 ( Istex/Corpus ); précédent : 000F63; suivant : 000F65Synthesis 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 ; Ivan JabinSource :
- 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.
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DOI: 10.1002/chem.200701051
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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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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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Several <i>C</i><sub>3</sub>‐ or <i>C</i><sub>3<i>v</i></sub>‐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 <b>12</b>, 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 <b>12</b> 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.</p></abstract><abstract type="graphical" xml:lang="en"><p>“<b>Cryptic” heteroditopic receptors</b>: Tripodal amido caps have been efficiently grafted onto the narrow rim of a calix[6]arene through peptide‐coupling reactions. The resulting calix[6]cryptamides display a well‐defined hydrophobic cavity closed by convergent amide groups, which gives two distinct binding sites. 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Roosevelt 50, CP160/06, 1050 Brussels, Belgium, Fax: (+32) 2‐650‐27‐98</affiliation><affiliation>E-mail: ijabin@ulb.ac.be</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="article" displayLabel="article"></genre><originInfo><publisher>WILEY‐VCH Verlag</publisher><place><placeTerm type="text">Weinheim</placeTerm></place><dateIssued encoding="w3cdtf">2008-01-07</dateIssued><dateCaptured encoding="w3cdtf">2007-07-09</dateCaptured><copyrightDate encoding="w3cdtf">2008</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><internetMediaType>text/html</internetMediaType><extent unit="figures">12</extent><extent unit="tables">4</extent><extent unit="references">92</extent></physicalDescription><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.</abstract><abstract>“Cryptic” heteroditopic receptors: Tripodal amido caps have been efficiently grafted onto the narrow rim of a calix[6]arene through peptide‐coupling reactions. The resulting calix[6]cryptamides display a well‐defined hydrophobic cavity closed by convergent amide groups, which gives two distinct binding sites. These receptors can bind neutral guests or organic ion‐pair salts, and even show chiral guest recognition in the calixarene cavity (see figure).</abstract><note type="funding">French Ministry of Research</note><subject lang="en"><genre>keywords</genre><topic>calixarenes</topic><topic>host–guest systems</topic><topic>ion pairs</topic><topic>molecular recognition</topic><topic>supramolecular chemistry</topic></subject><relatedItem type="host"><titleInfo><title>Chemistry – A European Journal</title></titleInfo><titleInfo type="abbreviated"><title>Chemistry – A European Journal</title></titleInfo><genre type="journal">journal</genre><note type="content"> Supporting information for this article is available on the WWW under http://www.wiley‐vch.de/contents/jc_2111/2008/f701051_s.pdf or from the author.</note><subject><genre>article-category</genre><topic>Full Paper</topic></subject><identifier type="ISSN">0947-6539</identifier><identifier type="eISSN">1521-3765</identifier><identifier type="DOI">10.1002/(ISSN)1521-3765</identifier><identifier type="PublisherID">CHEM</identifier><part><date>2008</date><detail type="volume"><caption>vol.</caption><number>14</number></detail><detail type="issue"><caption>no.</caption><number>2</number></detail><extent unit="pages"><start>548</start><end>557</end><total>10</total></extent></part></relatedItem><identifier type="istex">BBFBBA0A0701DFDEA0231F02BAA881D1DC1A30D8</identifier><identifier type="DOI">10.1002/chem.200701051</identifier><identifier type="ArticleID">CHEM200701051</identifier><accessCondition type="use and reproduction" contentType="copyright">Copyright © 2008 WILEY‐VCH Verlag GmbH & Co. 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