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  • Template synthesis  (5)
  • Host-guest chemistry  (4)
  • rotaxanes  (4)
  • 1
    Electronic Resource
    Electronic Resource
    Ein makrobicyclischer Großhohlraum zur selektiven Komplexierung von Alkalimetall-Ionen (1989)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 122 (1989), S. 2391-2393 
    Details
    ISSN: 0009-2940
    Keywords: Host-guest chemistry ; Macrobicyclic ligand ; Alkali metal complexation ; Complex formation ; Cesium selectivity ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A Large Macrobicyclic cavity for the Selective Complexation of Alkali Metal IonsThe preparation of the new ligand 3 was carried out starting with the podand 8 and the triamine 11. Ligand 3 forms complexes with alkali metal ions in solution (chloroform) as well as under the conditions of FAB mass spectrometry, whereby Cs⊕ selectivity is observed.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19891221227
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  • 2
    Electronic Resource
    Electronic Resource
    Maßgeschneiderte Wirtverbindung für Piperazin und verwandte Amine (1993)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 126 (1993), S. 1003-1009 
    Details
    ISSN: 0009-2940
    Keywords: Diamine ; Host-guest chemistry ; Macrocycle ; Supramolecular chemistry ; Receptor molecule, synthetic ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Tailor-Made Host for Piperazine and Related AminesThe 38-membered bis-catechol 4b is obtained by cyclisation of the diacyl dichloride 3c with the diamine 2b in 45% yield, whereas a 68-membered octalactam 7 is formed under similar conditions from 5 and 1b. Bis-catechol 4b is a selective host compound for piperazine (8) and the structurally related diamine 9. Association constants for the 1:1 complexes have been measured by 1H-NMR titration experiments. A nucleobase guest (pterine, 24) was extracted into a hydrochloric acid phase by complex formation with the host 4b. The results are compared with solubility and transport experiments obtained by use of analogous macrobicyclic tris-catechol hosts.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19931260421
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  • 3
    Electronic Resource
    Electronic Resource
    Templat-Synthese makrobicyclischer Großhohlräume vom Tris(bipyridin)-Typ (1989)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 122 (1989), S. 1725-1727 
    Details
    ISSN: 0009-2940
    Keywords: Cryptands ; Macrobicyclic ligands ; Template synthesis ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Template Synthesis of Macrobicyclic Large Cavities of the Tris-(bipyridine)-TypeThe synthesis of the ligands 2 and 3 has been performed in a one-step procedure starting with the triamines 11 and 12 and 5,5′-bis(bromomethyl)-2,2′-bipyridine (6). The new macrobicyclic compounds were isolated and characterized as their sodium complexes. Dynamic 1H-NMR investigations reveal the conformational flexibility of the complex 2 · Na⊕.
    Notes: Die Liganden 2 und 3 wurden in einer Eintopf-Synthese ausgehend von den Triaminen 11 und 12 sowie 5,5′-Bis(brommethyl-2,2′-bipyridin (6) erhalten und als Natrium-Komplexe isoliert und charakterisiert. Die dynamische 1H-NMR-Spektroskopie des Komplexes 2 · Na⊕ belegt seine konformative Beweglichkeit.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19891220920
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  • 4
    Electronic Resource
    Electronic Resource
    Flexible, Long-Chain Alkanediamines as Building Blocks for Catenanes - Steric Hindrance of Circumrotation by DerivatizationDedicated to Professor Vincenzo Balzani, Bologna, on the occasion of his 60th birthday. (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 761-766 
    Details
    ISSN: 0947-3440
    Keywords: Catenanes ; Circumrotation ; Macrocycles ; Mechanical bonds ; Template syntheses ; Host-guest chemistry ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: New catenanes of the amide-linked type, such as 11 with one macrocycle containing two (CH2)12 chains are synthesized from long-chain alkanediamines in yields of up to 21%. Consequently, the preorganization afforded by fixed and angular building units - so far considered essential - proves not to be necessary. The new sulfonamide catenanes exhibit high conformational flexibility. However, the circumrotation of one of the macrocycles can be hindered by substitution with bipyridine units at the sulfonamide nitrogen.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970420
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  • 5
    Electronic Resource
    Electronic Resource
    Non-Ionic Template Synthesis of Amide-Linked Rotaxanes: Olefinic and Aliphatic Axle Building Blocks (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 2269-2273 
    Details
    ISSN: 0947-3440
    Keywords: Association constant ; Mechanical bonding ; Molecular recognition ; Template synthesis ; Supramolecular chemistry ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The first synthesis of amide-linked rotaxanes with non-arene axle building blocks is reported. The threading synthesis of rotaxane 8 with olefinic fumaryl chloride proves that arene moieties are not necessary for non-ionic template syntheses. Mass spectroscopic evidence of a rotaxane bearing an aliphatic axle, derived from succinic acid, revealed that hydrogen bonding, rather than π,π interactions, is the predominant template binding force. 1H-NMR titration studies on the threading synthesis of these mechanically bonded molecules were carried out. The association constants measured suggest that the incorporation of the corresponding monoamide monochloride (cf. 7), rather than the incorporation of the diacid dichloride (cf. 5), plays the key role in these rotaxane syntheses. The X-ray structural analysis of a semi axle (14) reveals hydrogen bonding patterns characteristic of diamides.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719971114
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  • 6
    Electronic Resource
    Electronic Resource
    A [3]rotaxane of the amide type (1996)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 2 (1996), S. 640-643 
    Details
    ISSN: 0947-6539
    Keywords: lactam ; macrocycles ; rotaxanes ; self-assembly ; template syntheses ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Two new rotaxane types, the [2]rotaxanes 12a,b and the [3]rotaxane 13, have been synthesised by treating the “axle” 7 with the stopper component 9 in the presence of the “wheel” 8. A nonionic template intermediate of type 10 is proposed. The [3]rotaxane 13 was only obtained when the chain of the “axle” had a certain length: with n = 1 only [2]rotaxane 12 a was isolated, whereas with n = 2 the [3]rotaxane 13 was formed besides the [2]rotaxane 12 b. This suggests that more extended rotaxanes and polyrotaxanes can be synthesised by the template strategy.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.1460020605
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  • 7
    Electronic Resource
    Electronic Resource
    Synthesis of Rotaxane AssembliesChemistry with rotaxanes, part II. For part I, see: R. Jäger, M. Händel, J. Harren, K. Rissanen, F. Vögtle, Liebigs Ann. 1996, 1201. (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 2043-2051 
    Details
    ISSN: 0947-6539
    Keywords: macrocycles ; rotaxanes ; sulfon-amides ; supramolecular chemistry ; template synthesis ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The preparative syntheses of new nano-sized rotaxane assemblies are described, namely, of the first tris[2]rotaxane, 15, the first bis[2]rotaxane connected at the axles, 4, and the first [3]rotaxane with two different axles, 12 (unsymmetrical “bis[2]rotaxane”). These syntheses were made possible by the directed incorporation of a sulfonamide group into the amide-linked rotaxane building blocks. The sulfonamide moiety can be used as a functional group in alkylation reactions, allowing the further attachment of building blocks in good yields. The successful synthesis of these new rotaxane architectures demonstrates the synthetic potential of this sulfonamide strategy in the preparation of multirotaxane and dendritic rotaxane structures.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970031220
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  • 8
    Electronic Resource
    Electronic Resource
    Calixarenes as Stoppers in Rotaxanes (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 155-161 
    Details
    ISSN: 1434-193X
    Keywords: Mechanical bonding ; Interlocked molecules ; Template synthesis ; Calixarenes ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of the amide-based rotaxane 7a bearing calix[4]arene blocking groups is described for the first time. While rotaxane formation fails if a calix[4]arene is functionalized at the upper rim with only an amino or methylamino group lacking any spacer, the prolonged amine 5a works successfully as stopper unit preventing dethreading of the dimeric wheel 1a by its size. Rotaxane formation of 8b was observed only by MALDI-TOF mass spectrometry of the reaction mixture of the amine 5b, the axle 6 and 1a. With the larger trimeric wheel 1b no stable rotaxane could be obtained. It either does not act as a concave template or its opening is too wide, even for the bulky calixarene stoppers.
    Type of Medium: Electronic Resource
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  • 9
    Electronic Resource
    Electronic Resource
    Host/Guest Chemistry of Organic Onium Compounds - Clathrates, Crystalline Complexes, and Molecular Inclusion Compounds in Aqueous Solution (1985)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 24 (1985), S. 727-742 
    Details
    ISSN: 0570-0833
    Keywords: Host-guest chemistry ; Onium compounds ; Clathrates ; Inclusion compounds ; Macrocycles ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The importance of organic onium compounds for host/guest interactions in biological processes has been long recognized. In contrast, the versatility of synthetic onium compounds as host molecules in abiotic chemistry has only been investigated in detail for the last few years. Due to their inclusion ability and selectivities, organic ammonium, pyridinium, and phosphonium salts and other organic salts with specific structural features are interesting as clathrate-forming molecules. The crystal structures of the clathrates afford insight into the conformational adaptability of onium clathrands with limited flexibility to the geometric requirements of the guest molecules. Optically active onium hosts can be used for enantiomeric enrichment. In crystalline tetracyanoquinodimethane(TCNQ) complexes and radical anion salts, the structure of the organic heterocation has a marked effect on the electrical conductivity. Macrocyclic onium compounds of the phane type with “exohydrophilic” and “endolipophilic” cavities are suitable as models of enzymes and biological receptors. They can also be used to transfer aromatic and aliphatic guest molecules selectively into aqueous solution. Catalytic activity (including H/D exchange) has already been obtained with synthetic compounds having large cavities. The further development of such host/guest systems may contribute to the understanding of biological systems and the improvement of technical processes (catalysis in molecular cavities).
    Additional Material: 22 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.198507271
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  • 10
    Electronic Resource
    Electronic Resource
    Synthesis of Rotaxanes by Brief Melting of Wheel and Axle ComponentsDedicated to Professor Sigrid D. Peyerimhoff on the occasion of her 60th birthday (1997)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 36 (1997), S. 1199-1201 
    Details
    ISSN: 0570-0833
    Keywords: macrocycles ; mechanical binding ; rotaxanes ; supramolecular chemistry ; synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.199711991
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