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  • 1
    Electronic Resource
    Electronic Resource
    Template synthesis of the first amide-based rotaxanes (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 739-743 
    Details
    ISSN: 0947-3440
    Keywords: Interlocked rings ; Macrocycles ; Mechanical bond ; Rotaxanes ; Template effect ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The first rotaxanes 6a, 6b and 11 with an amide structure are described. Their (supramolecular template) syntheses are strikingly simple. The central part of the „axle“ is added to the „wheel“ and subsequently capped. The macromonocycle („wheel“) provides the receptor cavity for the „axle“ and the triphenylmethane stoppers confirm the mechanical bond between „wheel“ and „axle“.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199505109
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  • 2
    Electronic Resource
    Electronic Resource
    Sulfonamide-based catenanes  -  regioselective template synthesisDedicated to Professor Hans Jürgen Bestman at the occasion of his 70th birthday. (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 1855-1860 
    Details
    ISSN: 0947-3440
    Keywords: Catenane synthesis ; Macrocycles ; Molecular recognition ; Sulfonamides ; Intertwining mechanism ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The first catenanes containing sulfonamide units were synthesized. Selective formation of the in/out isomer 7 can be explained by host-guest interactions that cause a regioselective templating effect. Replacement of O2S-NH by O2S-NMe increases the yield significantly (from 10 to 19%). The sulfonamide catenane 7 has a topologically chiral structure.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199510260
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  • 3
    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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  • 4
    Electronic Resource
    Electronic Resource
    Molecular Ribbons Containing Pyridine Rings (1996)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1996 (1996), S. 2115-2121 
    Details
    ISSN: 0947-3440
    Keywords: Cyclophanes ; Macrocycles ; Phanes ; Pyridinophanes ; Ring compounds ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The first synthesis of the ribbon-like compounds 6-10 is described. The new building block diethyl 2,6-bis(bromomethyl)pyridine-3,5-dicarboxylate 1 was prepared and characterized. Single-crystal X-ray structure analyses indicate that these ribbon-like molecules arrange in a folded conformation, with the pyridine and benzene units being folded in a face-to-face manner, and the tosyl units of 8-10 pointing outwards. The “intramolecular self-assembly” (folding) of these molecular ribbons is primarily attributable to the energetically more favourable syn conformation of both the [3.3]metacyclophanes and the pyridinophanes.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199619961225
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  • 5
    Electronic Resource
    Electronic Resource
    A Macrocyclic Tetraazapolyene - Synthesis and Configuration (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 671-672 
    Details
    ISSN: 0009-2940
    Keywords: Azines ; Bis(azines) ; Macrocycles ; Tetraazapolyenes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The new macrocyclic bis(azine) 2 forming yellow microcrystals has been prepared in 72% yield by treating the diketone 1 with hydrazine hydrate under high-dilution conditions. In contrast to the UV/Vis spectrum of the “open-chain” azine 4, that of 2 shows characteristic features of a polyene chromophore containing (Z)-configurated double bonds.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240335
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  • 6
    Electronic Resource
    Electronic Resource
    Großflächige, starre Makrocyclen aus 1,4-Diphenylbutadiin-Bauteilen (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 909-913 
    Details
    ISSN: 0009-2940
    Keywords: Diphenylbutadiynophane ; Eglinton reaction ; Macrocycles ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Flat and Rigid Macrocycles Based on 1,4-Diphenylbutadiyne Units[1.1](3,3′)-1,4-Diphenylbutadiynophanes of type Ia,b (e.g. 1 - 4) are obtained by coupling the diethynyl derivatives 18 - 21 by means of CuCl/CuCl2. The properties of 1 - 4 (UV, NMR, charge transfer) are compared to 1,4-diphenylbutadiyne. In contrast to 1,4-diphenylbutadiyne, 1 and 2 (type Ia) are highmelting, colorless solids, which are sparingly soluble in common organic solvents. The better soluble compounds 3 and 4 (type Ib) are also prepared. The macrocycles 1 - 4 consist of two “isolated” 1,4-diphenylbutadiyne units. In contrast to 1,4-diphenylbutadiyne they do not seem to form charge-transfer complexes with tetracyanoethene (TCNE) in CH2Cl2.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240435
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  • 7
    Electronic Resource
    Electronic Resource
    Makrocyclisch modifizierte Verbindungen vom TTF- und TCNQ-Typ (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 897-902 
    Details
    ISSN: 0009-2940
    Keywords: Biphenylophane ; Kharasch coupling reaction ; Macrocycles ; TCNQ ; TTF ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Molecules of the TTF and TCNQ Type with Macrocyclic SkeletonsThe electron-rich and electron-poor macrocycles 1 - 3 have been synthesized. Their [1.1](3,3′)biphenylophane framework is formed by Kharasch reaction. Whereas in the well-known donors and acceptors I-III the functionalities are conjugated, in their macrocyclic “analogues” 1-3 the conjugation is prevented by the meta-connection of the phenylene rings. The redox properties  - studied by cyclovoltammetry  -  are discussed. The X-ray analysis of 3 shows considerable deviations from a planar structure.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240433
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  • 8
    Electronic Resource
    Electronic Resource
    all-Homocalixarene: Carbocyclische Wirtverbindungen mit intra- und extraannularen Ligandarmen (1993)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 126 (1993), S. 2483-2491 
    Details
    ISSN: 0009-2940
    Keywords: Carbocycles ; Homocalixarenes ; Calixarenes, Homo- ; Large rings ; Macrocycles ; [2n]Metacyclophanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: all-Homocalixarenes: Carbocyclic Host Compounds with Intra- and Extraannular Ligand ArmsMethoxy-substituted [2n]metacyclophanes 1-10, obtained by Müller-Röscheisen cyclization, are converted into all-homocalixarenes 11-20 with free phenolic hydroxy functions. The well-soluble cyclic pentamer 11 and octamer 14 with endo-acidic host properties are investigated with regard to guest binding. They exhibit selectivity towards alkaline earth metal ions (Ba2+) in liquid/liquid extraction studies. Some of the macrocyclic oligophenols are transformed into homocalixarenes 21-25 with intra- or extraannular oxapropionate groups. The diester 22 and the tetraester 23 are converted into carbocycles 26 and 27 with two and four free oxapropionic acid groups. Complexation properties of the oligoesters in extraction studies and log K values in water are reported. X-ray structural analyses were performed of the [6]-, [8]- and [4]- homocalixarenes 9 and 21, 14 and 23; the inclusion of solvent molecules is proven.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19931261123
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  • 9
    Electronic Resource
    Electronic Resource
    Konkave Farbstoffe mit Azobenzol-Einheiten als Chromophore, Photoschaltelemente und hohlraumbildende Bausteine (1992)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 125 (1992), S. 1675-1686 
    Details
    ISSN: 0009-2940
    Keywords: Azobenzene ; Concave dyes ; Dyes ; Isomerism, in-out ; Macrocycles ; Molecular switches ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Concave Dyes with Azobenzene Units as Chromophores, Photoswitchable and Cavity-Forming ElementsFive monomacrocyclic (12a-e) and three types of threefold azobenzene-bridged oligomacrocyclic compounds (15, 17, 28, 31) have been synthesized. Due to the cavity-forming chromophores at the periphery of these molecules they represent concave dyes. The watersoluble monocycles 12b-e were photoisomerized and investigated before and after E/Z isomerization with regard to their host properties for small neutral organic guest compounds. The bicyclic azobenzene derivative 31 with triphenylethane spacers exhibits in/out isomerism. The in/out isomer 31c was separated by HPLC from 31a and b, which are in equilibrium at room temperature. The tris(2-aminoethyl)amine-capped Schiff bases 15 and 17 form complexes with Cu(CH3CN)4BF4.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19921250725
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  • 10
    Electronic Resource
    Electronic Resource
    Präorganisierte Bis-ethine: Molekulare π-Pinzetten? (1990)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 1097-1103 
    Details
    ISSN: 0009-2940
    Keywords: Bond formation, C-C ; Iron complexes ; Macrocycles ; Molecular tweezers ; Naphthalenophane ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Preorganized Bis-ethynes: Molecular π-Tweezers?1,8-Bis[(arylethynylphenyl)]naphthalenes of type V (e.g. 10, 11) and 1,8-bis[(arylethenylphenyl)]naphthalenes (6, 6a, 7, 7a) were synthesized for the first time. In contrast to the known 1,8-bis(arylethynyl)naphthalenes VI their “stereologs” 10 and 11 are thermally stabile. Yet they react with pentacarbonyliron to yield dinuclear transition metal complexes of the type 12, 13, i.e. a strained cyclophane macrocycle is formed by C-C bond formation. The X-ray analysis of the di-tert-butyl compound 11 shows that the peri substituents diverge, but with increasing distance from the naphthalene skeleton one of the arylethynyl units is bent to the opposite direction (Figure 2). The question whether the new molecular skeleton V can be viewed as molecular tweezers is discussed: as the hydrocarbons react irreversibly with transition metal carbonyls, they may rather be taken as “tweezers for single use”.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19901230524
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