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Pure Appl. Chem., 1978, Vol. 50, No. 9-10, pp. 871-892

http://dx.doi.org/10.1351/pac197850090871

Cryptates: inclusion complexes of macropolycyclic receptor molecules

J. M. Lehn

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  • Ahlers Benedikt, Cammann Karl, Warzeska Sabine, Krämer Roland: Molekulare Erkennung von Cyanid durch einen makrocyclischen Dikupfer(II)-Ionophor: Konstruktion einer cyanidselektiven Flüssigmembran-Elektrode. Angew Chem 1996, 108, 2270. <http://dx.doi.org/10.1002/ange.19961081825>
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  • Silaghi-Dumitrescu Luminita, Gibbons Martin N., Silaghi-Dumitrescu Ioan, Zukerman-Schpector Julio, Haiduc Ionel, Sowerby D.Bryan: Oxidation of (AsPh2)2E(E=O or S); supramolecular hydrogen-bonded self-assembly of an unusual tetranuclear adduct and crystal structure of [AsPh2(O)OH · AsPh2(S)OH]2. J Organomet Chem 1996, 517, 101. <http://dx.doi.org/10.1016/0022-328X(96)06154-2>
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  • Behle Lutz, Neuburger Markus, Zehnder Margaretha, Kaden Thomas A.: Metal Complexes with Macrocyclic Ligands. Part XXXIX. Mono- and binuclear copper(II) complexes of a bridging bis[1, 4, 7-triazacyclononane]. HCA 1995, 78, 693. <http://dx.doi.org/10.1002/hlca.19950780316>
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  • Cukrowski Ignacy, Marsicano Fabrizio, Hancock Robert D., Tshetlho Pulane T., Van Otterlo Willem A.L.: The neutral oxygen donor in complexes of lead and cadmium: A differential pulse polarographic, potentiometric and calorimetric study. J Polyhedron 1995, 14, 1661. <http://dx.doi.org/10.1016/0277-5387(94)00428-H>
  • Haiduc Ionel, Sowerby D.Bryan, Lu Shao-Fang: Stereochemical aspects of phosphor-1,1-dithiolato metal complexes (dithiophosphates, dithiophosphinates): Coordination patterns, molecular structures and supramolecular associations—I. J Polyhedron 1995, 14, 3389. <http://dx.doi.org/10.1016/0277-5387(95)00108-5>
  • Mathur A. M., Scranton A. B.: Synthesis and Ion-Binding Properties of Polymeric Pseudocrown Ethers: A Molecular Dynamics Study. SEPARAT SCI 1995, 30, 1071. <http://dx.doi.org/10.1080/01496399508010333>
  • Coppola M., Catinella S., Traldi P., Guerriero P., Tamburini S., Vigato P. A.: Fast atom bombardment mass spectrometry of new polydentate schiff bases. 2. The case of mono- and bisaldimines containing pyridine groups. Org Mass Spectrom 1994, 29, 566. <http://dx.doi.org/10.1002/oms.1210291010>
  • Catinella S., Traldi P., Guerriero P., Tamburini S., Vigato P. A.: Fast-atom bombardment mass spectrometry of new polydentate schiff bases. 1. The case of variously substituted mono-and bis-salicylaldimine derivatives. Rapid Commun Mass Spectrom 1994, 8, 111. <http://dx.doi.org/10.1002/rcm.1290080121>
  • Casas José S., Castiñeiras Alfonso, Ionel Haiduc, Sánchez Agustín, Sordo José, Vázquez-López Ezequiel M.: Supramolecular self-organization in catena-poly [dimethyl(diphenylphosphinothioato)thallium(III)], [TlMe2{S(O)PPh2{]n, a polymer with secondary interactions between the chain segments. J Polyhedron 1994, 13, 1805. <http://dx.doi.org/10.1016/0277-5387(94)80001-4>
  • Guerriero P., Tamburini S., Vigato P.A., Russo U., Benelli C.: Mössbauer and magnetic properties of mononuclear, homo- and hetero-dinuclear complexes. Inorg Chim Ada 1993, 213, 279. <http://dx.doi.org/10.1016/S0020-1693(00)83838-4>
  • Cesario Michele, Guilhem Jean, Pascard Claudine: Anion complexes between a macrocyclic cyclophane and squaric acid: The crystal structure reveals the ideal receptor topology ordered by the substrate. Supramol Chem 1993, 2, 331. <http://dx.doi.org/10.1080/10610279308029827>
  • Teo Boon K., Zhang Hong: Molekulare Maschinen: Molekülstruktur von [(p-Tol3P)10Au13Ag12Cl8](PF6) — ein Cluster mit einem biikosaedrischen, rotorähnlichen Metallgerüst und einer ungewöhnlichen Anordnung von Brückenliganden. Angew Chem 1992, 104, 447. <http://dx.doi.org/10.1002/ange.19921040414>
  • Lehn Jean-Marie, De Vains Jean-Bernard Regnouf: Synthesis and Properties of Macrobicyclic Cryptates Incorporating Five- and Six-Membered Biheteroaryl Units. HCA 1992, 75, 1221. <http://dx.doi.org/10.1002/hlca.19920750422>
  • Krakowiak Krzysztof E., Bradshaw Jerald S.: Syntheses of the Cryptands. A Short Review. Isr. J. Chem. 1992, 32, 3. <http://dx.doi.org/10.1002/ijch.199200002>
  • Guerriero P., Tamburini S., Vigato P. A., Catinella S., Traldi P.: Mass spectrometric studies on some macrocyclic, macrobicyclic and macroacyclic Schiff bases. Rapid Commun Mass Spectrom 1992, 6, 741. <http://dx.doi.org/10.1002/rcm.1290061206>
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  • Aguiari A., Bullita E., Casellato U., Guerriero P., Tamburini S., Vigato P.A.: Macrocyclic and macroacyclic compartmental Schiff bases: synthesis, characterization, X-ray structure and interaction with metal ions. Inorg Chim Ada 1992, 202, 157. <http://dx.doi.org/10.1016/S0020-1693(00)86831-0>
  • Parham Hooshang, Shamsipur Mojtaba: Spectrophotometric study of some alkali and alkaline earth cryptates in dimethylformamide solution using murexide as a metallochromic indicator. J Polyhedron 1992, 11, 987. <http://dx.doi.org/10.1016/S0277-5387(00)83352-5>
  • Bocheńska M., Biernat J. F., Bradshaw J. S.: Sulfonamides as Ion-Carriers. J Coord Chem 1992, 27, 129. <http://dx.doi.org/10.1080/00958979209407949>
  • Auffinger P., Wipff G.: Molecular dynamics simulations on the protonated 222. H+ and 222.2H+ cryptands in water:Endo versusexo conformations. J Incl Phenom Macrocycl Chem 1991, 11, 71. <http://dx.doi.org/10.1007/BF01073686>
  • Lehn Jean-Marie: Perspektiven der Supramolekularen Chemie – von der molekularen Erkennung zur molekularen Informationsverarbeitung und Selbstorganisation. Angew Chem 1990, 102, 1347. <http://dx.doi.org/10.1002/ange.19901021117>
  • Holý Petr, Morf Werner E., Seller Kurt, Simon Wilhelm, Vigneron Jean-Pierre: Enantioselective Optode Membranes with Enantiomer Selectivity for (R)- and (S)-l-Phenylethylammonium Ions. HCA 1990, 73, 1171. <http://dx.doi.org/10.1002/hlca.19900730505>
  • Beer Paul D., Keefe Anthony D.: A new approach to the coordination of anions, novel polycobalticinium macrocyclic receptor molecules. J Organomet Chem 1989, 375, C40. <http://dx.doi.org/10.1016/0022-328X(89)85105-8>
  • Dietrich Bernard, Lehn Jean-Marie, Guilhem Jean, Pascard Claudine: Anion receptor molecules : Synthesis of an octaaza-cryptand and structure of its fluoride cryptate. Tetrahetron Lett 1989, 30, 4125. <http://dx.doi.org/10.1016/S0040-4039(00)99339-0>
  • Lehn Jean-Marie: Supramolekulare Chemie – Moleküle, Übermoleküle und molekulare Funktionseinheiten (Nobel-Vortrag). Angew Chem 1988, 100, 91. <http://dx.doi.org/10.1002/ange.19881000110>
  • Diederich François: Cyclophane zur Komplexierung von Neutralmolekülen. Angew Chem 1988, 100, 372. <http://dx.doi.org/10.1002/ange.19881000307>
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  • Hosseini Mir Wais, Lehn Jean-Marie: Anion-receptor molecules: Macrocyclic and macrobicyclic effects on anion binding by polyammonium receptor molecules. HCA 1988, 71, 749. <http://dx.doi.org/10.1002/hlca.19880710409>
  • Alpha Béatrice, Anklam Elke, Deschenaux Robert, Lehn Jean-Marie, Pietraskiewiez Marek: Synthesis and Characterisation of the Sodium and Lithium Cryptates of Macrobicyclic Ligands incorporating pyridine, bipyridine, and biisoquinoline units. HCA 1988, 71, 1042. <http://dx.doi.org/10.1002/hlca.19880710515>
  • Lehn Jean-Marie: Supramolecular chemistry — Scope and perspectives: Molecules — Supermolecules — Molecular devices. J Incl Phenom Macrocycl Chem 1988, 6, 351. <http://dx.doi.org/10.1007/BF00658981>
  • Politzer Peter, Sukumar Nagamani, Nagata Chikayoshi, Aida Misako, Owenson Brian, MacElroy Robert D., Pohorille Andrew: An examination of some effects of OH rotation in phenol and p-nitrophenol. Journal of Molecular Structure: THEOCHEM 1988, 179, 439. <http://dx.doi.org/10.1016/0166-1280(88)80142-8>
  • Cox B.G., Stroka J., Schneider H.: Kinetic studies and thermodynamic results for complex formation and solvation of thallium(I) cryptates in acetonitrile and in acetonitrile-water mixtures. Inorg Chim Ada 1988, 147, 9. <http://dx.doi.org/10.1016/S0020-1693(00)80623-4>
  • Jung Michael E., Xia Haiji: Synthesis and transport properties of 12-silacrown-3, a new type of anion complexing agent. Tetrahetron Lett 1988, 29, 297. <http://dx.doi.org/10.1016/S0040-4039(00)80078-7>
  • Fujita Terunori, Lehn Jean-Marie: Synthesis of dome-shaped cyclophane type macrotricyclic anion receptor molecules. Tetrahetron Lett 1988, 29, 1709. <http://dx.doi.org/10.1016/S0040-4039(00)82024-9>
  • Jurczak Janusz, Ostaszewski Ryszard: The application of ultrasound to N-methylation of diazacoronands. Tetrahetron Lett 1988, 29, 959. <http://dx.doi.org/10.1016/S0040-4039(00)82493-4>
  • Blacker A. John, Jazwinski Jaroslaw, Lehn Jean-Marie: Molecular Anion Binding and Substrate Photooxidation in Visible Light by 2,7-Diazapyrenium Cations. HCA 1987, 70, 1. <http://dx.doi.org/10.1002/hlca.19870700102>
  • Fujii Yukio, Pacey Gilbert E.: Investigatins of the extraction of adenosine phosphates with N,N′-dioctadecyl-1,4-diazabicyclo[2.2.2.]octane and N,N,N′,N′-tetramethyl-N,N′-dioctadecyldiammonium alkanes. Analytica Chimica Acta 1987, 200, 181. <http://dx.doi.org/10.1016/S0003-2670(00)83768-X>
  • Castera Pierre, Faucher Jean-Paul, Granier Michel, Labarre Jean-François: SINGLY, DOUBLY AND TRIPLY BRIDGED POLYAZAHETEROPHANES DERIVED FROM HEXACHLOROCYCLOTRIPHOSPHAZENE, N3P3Cl6. Phosphorous and Sulfur and the Related Elements 1987, 32, 37. <http://dx.doi.org/10.1080/03086648708080650>
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  • Hosseini Mir Wais, Lehn Jean-Marie: Anion Coreceptor Molecules. Linear Molecular Recognition in the Selective Binding of Dicarboxylate Substrates by Ditopic Polyammonium Macrocycles. HCA 1986, 69, 587. <http://dx.doi.org/10.1002/hlca.19860690308>
  • Minyaev R. M.: Covalent chemical bonding through a bridging hydrogen atom in charged organic compounds. J Struct Chem 1986, 27, 126. <http://dx.doi.org/10.1007/BF00763581>
  • Heyer Dennis, Lehn Jean-Marie: Anion coordination chemistry - synthesis and anion binding features of cyclophane type macrobicyclic anion receptor molecules. Tetrahetron Lett 1986, 27, 5869. <http://dx.doi.org/10.1016/S0040-4039(00)85349-6>
  • Galatina A. I., Novikova N. S., Derkach L. G., Kramarenko N. L., Tsyguleva O. M., Kuzin V. F.: Structure and Mesomorphism of Cholesteric Liquid Crystals. Mol Liq Cryst 1986, 140, 11. <http://dx.doi.org/10.1080/00268948608080142>
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  • Arnaud-Neu Francoise, Sanchez Maria, Yahya Raïda, Schwing-Weill Marie-José, Lehn Jean-Marie: Nature et stabilité des complexes métalliques de cryptands dinucléants en solution. I. Polyazapolyoxa macrotricycle cylindrique et monocycle constitutif. HCA 1985, 68, 456. <http://dx.doi.org/10.1002/hlca.19850680219>
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  • Dietrich Bernard, Guilhem Jean, Lehn Jean-Marie, Pascard Claudine, Sonveaux Etienne: Molecular Recognition in Anion Coordination Chemistry. Structure, Binding Constants and Receptor-Substrate Complementarity of a Series of Anion Cryptates of a Macrobicyclic Receptor Molecule. HCA 1984, 67, 91. <http://dx.doi.org/10.1002/hlca.19840670112>
  • Rodriguz-Ubis Juan-Carlos, Alpha Béatrice, Plancherel Dominique, Lehn Jean-Marie: Photoactive cryptands. Synthesis of the sodium cryptates of macrobicyclic ligands containing bipyridine and phenoanthroline groups. HCA 1984, 67, 2264. <http://dx.doi.org/10.1002/hlca.19840670833>
  • Bocheńska Maria, Biernat Jan F.: Guanidinium-selective PVC membrane electrodes based on crown ethers. Analytica Chimica Acta 1984, 162, 369. <http://dx.doi.org/10.1016/S0003-2670(00)84259-2>
  • Dietrich Bernard, Hosseini Mir Wais, Lehn Jean-Marie, Sessions Richard B.: Synthesis and Protonation Features of 24-, 27- and 32-membered Macrocyclic Polyamines. HCA 1983, 66, 1262. <http://dx.doi.org/10.1002/hlca.19830660426>
  • Hosseini Mir Wais, Lehn Jean-Marie, Mertes Mathias P.: Efficient Molecular Catalysis of ATP-Hydrolysis by Protonated Macrocyclic Polyamines. HCA 1983, 66, 2454. <http://dx.doi.org/10.1002/hlca.19830660811>
  • Wipff G., Kollman P.A., Lehn J.M.: Macrocyclic receptor chemistry: Experimental and theoretical studies on molecular recognition. Journal of Molecular Structure: THEOCHEM 1983, 93, 153. <http://dx.doi.org/10.1016/0166-1280(83)80098-0>
  • Behr Jean-Paul, Lehn Jeau-Marie, Vierling Pierre: Molecular Receptors. Structural Effects and Substrate Recognition in Binding of Organic and Biogenic Ammonium Ions by Chiral Polyfunctional Macrocyclic Polyethers Bearing Amino-Acid and Other Side-Chains. HCA 1982, 65, 1853. <http://dx.doi.org/10.1002/hlca.19820650620>
  • Canceill Josette, Collet André, Gabard Jacqueline, Kotzyba-Hibert Florence, Lehn Jean-Marie: Speleands. Macropolycyclic receptor cages based on binding and shaping sub-units. Synthesis and properties of macrocycle cyclotriveratrylene combinations. Preliminary communication. HCA 1982, 65, 1894. <http://dx.doi.org/10.1002/hlca.19820650623>
  • Joll Scott T., Bradshaw Jerald S., Izatt Reed M.: Synthetic chiral macrocyclic crown ligands: A short review. J Heterocyclic Chem 1982, 19, 3. <http://dx.doi.org/10.1002/jhet.5570190101>
  • Schmidtchen Franz P.: Macrocyclische quartäre Ammoniumsalze, II1) Einschlußkomplexbildung mit Anionen in Lösung. Chem Ber 1981, 114, 597. <http://dx.doi.org/10.1002/cber.19811140219>
  • Bussmann Walter, Simon Wilhelm, Oesch Urs, Lehn Jean-Marie, Plumeré Pierre: Enantiomer-Selectivity for Phenylethylammonium Ion of Membranes Based on a Chiral Macrocyclic Polyether. HCA 1981, 64, 657. <http://dx.doi.org/10.1002/hlca.19810640308>
  • Graf Ernest, Lehn Jean-Marie: Cryptates Sphériques. Synthèse et Complexes d'Inclusion de Ligands Macrotricycliques Sphériques. HCA 1981, 64, 1040. <http://dx.doi.org/10.1002/hlca.19810640410>
  • Daly John J., Schönholzer Peter, Behr Jean-Paul, Lehn Jean-Marie: Molecular Structure of the Ethylenediammonium Complex of a Tetracarboxy-macrocyclic Receptor Molecule. HCA 1981, 64, 1444. <http://dx.doi.org/10.1002/hlca.19810640521>
  • Smid Johannes: Ion-chelating polymers carrying macrocyclic ligands. Makromolek Chem 1981, 5, 203. <http://dx.doi.org/10.1002/macp.1981.020051981112>
  • Hughes M.N.: Zinc and cadmium. Coord Chem Rev - 1981, 37, 297. <http://dx.doi.org/10.1016/S0010-8545(00)80485-3>
  • Behr Jean-Paul, Girodeau Jean-Marc, Hayward Rodney C., Lehn Jean-Marie, Sauvage Jean-Pierre: Molecular Receptors. Functionalized and chiral macrocyclic polyethers derived from tartaric acid. HCA 1980, 63, 2096. <http://dx.doi.org/10.1002/hlca.19800630736>
  • Lehn J.M., Vierling P.: The [18]-N3O3 aza-oxa macrocycle: a selective receptor unit for primary ammonium cations. Tetrahetron Lett 1980, 21, 1323. <http://dx.doi.org/10.1016/S0040-4039(00)74566-7>
  • Kotzyba-Hibert F., Lehn J.M., Vierling P.: Multisite molecular receptors and co-systems ammonium cryptates of macrotricyclic structures. Tetrahetron Lett 1980, 21, 941. <http://dx.doi.org/10.1016/S0040-4039(00)77745-8>
  • Vögtle Fritz, Müller Walter M.: Komplexe von γ-Cyclodextrin mit Kronenethern und Cryptanden sowie Coronaten und Cryptaten. Angew Chem 1979, 91, 676. <http://dx.doi.org/10.1002/ange.19790910831>
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  • Vögtle Fritz, Müller Walter M.: Complexes of γ-Cyclodextrin with Crown Ethers, Cryptands, Coronates, and Cryptates. Angew Chem Int Ed Engl 1979, 18, 623. <http://dx.doi.org/10.1002/anie.197906231>
  • Vögtle Fritz, Weber Edwin: Multidentate Acyclic Neutral Ligands and Their Complexation. Angew Chem Int Ed Engl 1979, 18, 753. <http://dx.doi.org/10.1002/anie.197907531>
  • Spiess Bernard, Arnaud-Neu Françoise, Schwing-Weill Marie-José: Complexation dans le méthanol anhydre de Cu (II) et Zn (II) par des ligands diaza-polyoxamacrocycliques. HCA 1979, 62, 1531. <http://dx.doi.org/10.1002/hlca.19790620518>
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