Efficient Synthesis of Calix[6]tmpa: A New Calix[6]azacryptand with Unique Conformational and Host–Guest Properties
Identifieur interne : 000A59 ( Istex/Curation ); précédent : 000A58; suivant : 000A60Efficient Synthesis of Calix[6]tmpa: A New Calix[6]azacryptand with Unique Conformational and Host–Guest Properties
Auteurs : Xianshun Zeng ; David Coquière ; Aurélie Alenda ; Eva Garrier ; Thierry Prangé [France] ; Yun Li ; Olivia Reinaud [France] ; Ivan Jabin [France]Source :
- Chemistry – A European Journal [ 0947-6539 ] ; 2006-08-16.
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Abstract
A new C3v‐symmetrical calix[6]azacryptand, that is, calix[6]tmpa (11), was synthesized by efficient [1+1] macrocyclization reactions. Remarkably, both linear and convergent synthetic strategies that were applied lead to equally good overall yields. Calix[6]tmpa behaves as a single proton sponge and appeared reluctant to undergo polyprotonation, unlike classical tris(2‐pyridylmethyl)amine (tmpa) derivatives. It also acts as a good host for ammonium ions. Interestingly, it strongly binds a sodium ion and a neutral guest molecule, such as a urea, an amide, or an alcohol, in a cooperative way. A 1H NMR study indicated that the ligand, as well as its complexes, adopt a major flattened cone conformation that is the opposite of that observed with the previously reported calix[6]cryptands. Characterization of the monoprotonated derivative 11⋅H+ by X‐ray diffraction also revealed the presence of a 1,3‐alternate conformation, which is the first example of its kind in the calix[6]arene family. This conformer is probably also present in solution as a minor species. The important covalent constraint induced by the polyaromatic tmpa cap on the calixarene skeleton, and conversely from the calix core onto the tmpa moiety, is the likely basis for the unique conformational and chemical properties of this host.
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DOI: 10.1002/chem.200600278
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Xianshun Zeng<affiliation><mods:affiliation>Unité de Recherche en Chimie Organique et Macromoléculaire (URCOM), Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre cedex, France, Fax: (+33) 232‐744‐391</mods:affiliation><wicri:noCountry code="subField">(+33) 232‐744‐391</wicri:noCountry></affiliation><affiliation><mods:affiliation>Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR CNRS 8601, Université René Descartes, 45 rue des Saints Pères, 75270 Paris cedex 06, France, Fax: (+33) 142‐862‐183</mods:affiliation><wicri:noCountry code="subField">(+33) 142‐862‐183</wicri:noCountry></affiliation><affiliation><mods:affiliation>Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR CNRS 8601, Université René Descartes, 45 rue des Saints Pères, 75270 Paris cedex 06, France, Fax: (+33) 142‐862‐183</mods:affiliation><wicri:noCountry code="subField">(+33) 142‐862‐183</wicri:noCountry></affiliation><affiliation><mods:affiliation>Unité de Recherche en Chimie Organique et Macromoléculaire (URCOM), Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre cedex, France, Fax: (+33) 232‐744‐391</mods:affiliation><wicri:noCountry code="subField">(+33) 232‐744‐391</wicri:noCountry></affiliation><affiliation><mods:affiliation>Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR CNRS 8601, Université René Descartes, 45 rue des Saints Pères, 75270 Paris cedex 06, France, Fax: (+33) 142‐862‐183</mods:affiliation><wicri:noCountry code="subField">(+33) 142‐862‐183</wicri:noCountry></affiliation>Le document en format XML
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uniqKey="Zeng X" first="Xianshun" last="Zeng">Xianshun Zeng</name><affiliation><mods:affiliation>Unité de Recherche en Chimie Organique et Macromoléculaire (URCOM), Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre cedex, France, Fax: (+33) 232‐744‐391</mods:affiliation><wicri:noCountry code="subField">(+33) 232‐744‐391</wicri:noCountry></affiliation></author><author><name sortKey="Coquiere, David" sort="Coquiere, David" uniqKey="Coquiere D" first="David" last="Coquière">David Coquière</name><affiliation><mods:affiliation>Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR CNRS 8601, Université René Descartes, 45 rue des Saints Pères, 75270 Paris cedex 06, France, Fax: (+33) 142‐862‐183</mods:affiliation><wicri:noCountry code="subField">(+33) 142‐862‐183</wicri:noCountry></affiliation></author><author><name sortKey="Alenda, Aurelie" sort="Alenda, Aurelie" uniqKey="Alenda A" first="Aurélie" last="Alenda">Aurélie 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type="abbrev">Chemistry – A European Journal</title><idno type="ISSN">0947-6539</idno><idno type="eISSN">1521-3765</idno><imprint><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><date type="published" when="2006-08-16">2006-08-16</date><biblScope unit="volume">12</biblScope><biblScope unit="issue">24</biblScope><biblScope unit="page" from="6393">6393</biblScope><biblScope unit="page" to="6402">6402</biblScope></imprint><idno type="ISSN">0947-6539</idno></series><idno type="istex">276E5A53B355F5C51DCF91BFC515DB9A6B6EAB97</idno><idno type="DOI">10.1002/chem.200600278</idno><idno type="ArticleID">CHEM200600278</idno></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0947-6539</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>calixarenes</term><term>cryptands</term><term>host–guest systems</term><term>supramolecular chemistry</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract">A new C3v‐symmetrical calix[6]azacryptand, that is, calix[6]tmpa (11), was synthesized by efficient [1+1] macrocyclization reactions. Remarkably, both linear and convergent synthetic strategies that were applied lead to equally good overall yields. Calix[6]tmpa behaves as a single proton sponge and appeared reluctant to undergo polyprotonation, unlike classical tris(2‐pyridylmethyl)amine (tmpa) derivatives. It also acts as a good host for ammonium ions. Interestingly, it strongly binds a sodium ion and a neutral guest molecule, such as a urea, an amide, or an alcohol, in a cooperative way. A 1H NMR study indicated that the ligand, as well as its complexes, adopt a major flattened cone conformation that is the opposite of that observed with the previously reported calix[6]cryptands. Characterization of the monoprotonated derivative 11⋅H+ by X‐ray diffraction also revealed the presence of a 1,3‐alternate conformation, which is the first example of its kind in the calix[6]arene family. This conformer is probably also present in solution as a minor species. The important covalent constraint induced by the polyaromatic tmpa cap on the calixarene skeleton, and conversely from the calix core onto the tmpa moiety, is the likely basis for the unique conformational and chemical properties of this host.</div></front></TEI></record>Pour manipuler ce document sous Unix (Dilib)
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