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Supramolecular Chemistry Volume 17, 2005 - Issue 3
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Original Articles

A Calix[6]arene Receptor Rigidified by a Self-assembled Triammonium Cap: X-ray and NMR Characterization of the Binding of Polar Neutral Guests

Ulrich Darbost URCOM, Université du Havre, Faculté des Sciences et Techniques, 25 rue Philippe Lebon, BP 540, 76058, Le Havre cedex, France
,
Michel Giorgi Laboratoire de Cristallochimie, Université Paul Cézanne (Aix-Marseille III), Faculté des Sciences et Techniques, Avenue Escadrille Normandie-Niemen, 13397, Marseille cedex 20, France
,
Nicolas Hucher URCOM, Université du Havre, Faculté des Sciences et Techniques, 25 rue Philippe Lebon, BP 540, 76058, Le Havre cedex, France
,
Ivan Jabin * URCOM, Université du Havre, Faculté des Sciences et Techniques, 25 rue Philippe Lebon, BP 540, 76058, Le Havre cedex, France
&
Olivia Reinaud * Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR CNRS 8601, Université René Descartes, 45 rue des Saints-Pères, 75270, Paris cedex 06, France
Pages 243-250 | Received 08 Oct 2004, Accepted 18 Nov 2004, Published online: 19 Aug 2006

Citations (30)

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Stéphane Le Gac, Michel Giorgi & Ivan Jabin. (2007) Calix[6]arene Tris-carboxylic Acid Derivatives: X-ray and NMR Characterization of their Remarkable Host-guest Properties Toward Ammonium Ions. Supramolecular Chemistry 19:3, pages 185-197.
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Articles from other publishers (29)

Han-Wen Tian, Yan-Cen Liu & Dong-Sheng Guo. (2020) Assembling features of calixarene-based amphiphiles and supra-amphiphiles. Materials Chemistry Frontiers 4:1, pages 46-98.
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Gaël De Leener, Diana Over, Coryse Smet, Damien Cornut, Ana Gabriela Porras-Gutierrez, Isidoro López, Bénédicte Douziech, Nicolas Le Poul, Filip Topić, Kari Rissanen, Yves Le Mest, Ivan Jabin & Olivia Reinaud. (2017) “Two-Story” Calix[6]arene-Based Zinc and Copper Complexes: Structure, Properties, and O 2 Binding . Inorganic Chemistry 56:18, pages 10971-10983.
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Steven Moerkerke, Volodymyr Malytskyi, Lionel Marcélis, Johan Wouters & Ivan Jabin. (2017) Selective recognition of quaternary ammonium ions and zwitterions by using a biomimetic bis-calix[6]arene-based receptor. Organic & Biomolecular Chemistry 15:42, pages 8967-8974.
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Sara Zahim, Roy Lavendomme, Olivia Reinaud, Michel Luhmer, Gwilherm Evano & Ivan Jabin. (2016) Triflate-functionalized calix[6]arenes as versatile building-blocks: application to the synthesis of an inherently chiral Zn( ii ) complex . Organic & Biomolecular Chemistry 14:6, pages 1950-1957.
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Kinga Suwinska. 2016. Calixarenes and Beyond. Calixarenes and Beyond 1011 1036 .
Pierre-Edouard Danjou, Gaël De Leener, Damien Cornut, Steven Moerkerke, Samir Mameri, Angélique Lascaux, Johan Wouters, Andrea Brugnara, Benoit Colasson, Olivia Reinaud & Ivan Jabin. (2015) Supramolecular Assistance for the Selective Demethylation of Calixarene-Based Receptors. The Journal of Organic Chemistry 80:10, pages 5084-5091.
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Elena V. Ukhatskaya, Sergey V. Kurkov, Susan E. Matthews & Thorsteinn Loftsson. (2013) Encapsulation of Drug Molecules into Calix[n]arene Nanobaskets. Role of Aminocalix[n]arenes in Biopharmaceutical Field. Journal of Pharmaceutical Sciences 102:10, pages 3485-3512.
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Christopher Kremer & Arne Lützen. (2013) Artificial Allosteric Receptors. Chemistry – A European Journal 19:20, pages 6162-6196.
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Stéphane Le Gac, Ivan Jabin & Olivia Reinaud. 2012. Bioinspiration and Biomimicry in Chemistry. Bioinspiration and Biomimicry in Chemistry 367 395 .
Motohiro Nishio. (2011) The CH/π hydrogen bond in chemistry. Conformation, supramolecules, optical resolution and interactions involving carbohydrates. Physical Chemistry Chemical Physics 13:31, pages 13873.
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Stéphane Le Gac, Jean-François Picron, Olivia Reinaud & Ivan Jabin. (2011) Allosterically driven self-assemblies of interlocked calix[6]arene receptors. Organic & Biomolecular Chemistry 9:7, pages 2387.
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Angélique Lascaux, Stéphane Le Gac, Johan Wouters, Michel Luhmer & Ivan Jabin. (2010) An allosteric heteroditopic receptor for neutral guests and contact ion pairs with a remarkable selectivity for ammonium fluoride salts. Organic & Biomolecular Chemistry 8:20, pages 4607.
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Nicolas Le PoulBénédicte DouziechJoceline ZeitounyGrégory ThiabaudHélène ColasFrançoise ConanNathalie CosquerIvan JabinCorinne LagrostPhilippe HapiotOlivia ReinaudYves Le Mest. (2009) Mimicking the Protein Access Channel to a Metal Center: Effect of a Funnel Complex on Dissociative versus Associative Copper Redox Chemistry. Journal of the American Chemical Society 131:49, pages 17800-17807.
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Mickaël Ménand & Ivan Jabin. (2009) Synthesis of the First Calix[6]crypturea via a Versatile Tris-azide Precursor. Organic Letters 11:3, pages 673-676.
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David Coquière, Stéphane Le Gac, Ulrich Darbost, Olivier Sénèque, Ivan Jabin & Olivia Reinaud. (2009) Biomimetic and self-assembled calix[6]arene-based receptors for neutral molecules. Organic & Biomolecular Chemistry 7:12, pages 2485.
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Motohiro Nishio, Yoji Umezawa, Kazumasa Honda, Sei Tsuboyama & Hiroko Suezawa. (2009) CH/π hydrogen bonds in organic and organometallic chemistry. CrystEngComm 11:9, pages 1757.
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Jean-Alexandre Richard, Marc Pamart, Nicolas Hucher & Ivan Jabin. (2008) Synthesis and host–guest properties of a calix[6]arene based receptor closed by an internal ion-paired cap. Tetrahedron Letters 49:24, pages 3848-3852.
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Stéphane Le Gac, Jérôme Marrot & Ivan Jabin. (2008) Highly Selective Synthesis of a 1,3,5-Tris-Protected Calix[6]arene-Type Molecular Platform through Coordination and Host–Guest Chemistry. Chemistry - A European Journal 14:11, pages 3316-3322.
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Stéphane Le Gac & Ivan Jabin. (2007) 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. Chemistry – A European Journal 14:2, pages 548-557.
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Jun-Min Liu, Qi-Yu Zheng, Chuan-Feng Chen & Zhi-Tang Huang. (2007) Selectively formylated and bridged calix[6]arene derivatives at the upper rim. Tetrahedron 63:40, pages 9939-9946.
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Stéphane Le Gac, Michel Luhmer, Olivia Reinaud & Ivan Jabin. (2007) Self-assembly via ionic interactions of calix[6]arene-based receptors displaying remarkable host–guest properties toward neutral guests. Tetrahedron 63:44, pages 10721-10730.
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Ulrich Darbost, Olivier Sénèque, Yun Li, Gildas Bertho, Jérôme Marrot, Marie‐Noëlle Rager, Olivia Reinaud & Ivan Jabin. (2007) Allosteric Tuning of the Intra‐Cavity Binding Properties of a Calix[6]arene through External Binding to a Zn II Center Coordinated to Amino Side Chains . Chemistry – A European Journal 13:7, pages 2078-2088.
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Stéphane Le Gac, Xianshun Zeng, Camille Girardot & Ivan Jabin. (2006) Efficient Synthesis and Host−Guest Properties of a New Class of Calix[6]azacryptands. The Journal of Organic Chemistry 71:24, pages 9233-9236.
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Xianshun Zeng, David Coquière, Aurélie Alenda, Eva Garrier, Thierry Prangé, Yun Li, Olivia Reinaud & Ivan Jabin. (2006) Efficient Synthesis of Calix[6]tmpa: A New Calix[6]azacryptand with Unique Conformational and Host–Guest Properties. Chemistry – A European Journal 12:24, pages 6393-6402.
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Stéphane Le Gac, Jérôme Marrot, Olivia Reinaud & Ivan Jabin. (2006) Allosterically Coupled Double Induced Fit for 1+1+1+1 Self‐Assembly of a Calix[6]trisamine, a Calix[6]trisacid, and Their Guests. Angewandte Chemie International Edition 45:19, pages 3123-3126.
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Stéphane Le Gac, Jérôme Marrot, Olivia Reinaud & Ivan Jabin. (2006) Allosterically Coupled Double Induced Fit for 1+1+1+1 Self‐Assembly of a Calix[6]trisamine, a Calix[6]trisacid, and Their Guests. Angewandte Chemie 118:19, pages 3195-3198.
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Ulrich Darbost, Xianshun Zeng, Michel Giorgi & Ivan Jabin. (2005) Optically Pure Calix[6]tris-ammoniums:  Syntheses and Host−Guest Properties toward Neutral Guests. The Journal of Organic Chemistry 70:25, pages 10552-10560.
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Eva Garrier, Stéphane Le Gac & Ivan Jabin. (2005) First enantiopure calix[6]aza-cryptand: synthesis and chiral recognition properties towards neutral molecules. Tetrahedron: Asymmetry 16:23, pages 3767-3771.
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Ulrich DarbostMarie-Noëlle RagerSamuel PetitIvan JabinOlivia Reinaud. (2005) Polarizing a Hydrophobic Cavity for the Efficient Binding of Organic Guests:  The Case of Calix[6]tren, a Highly Efficient and Versatile Receptor for Neutral or Cationic Species. Journal of the American Chemical Society 127:23, pages 8517-8525.
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