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  • 1
    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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  • 2
    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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  • 3
    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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  • 4
    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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  • 5
    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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  • 6
    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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  • 7
    Electronic Resource
    Electronic Resource
    Gürtelförmige Moleküle mittels repetitiver Synthesestrategie (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 767-777 
    Details
    ISSN: 0009-2940
    Keywords: Azaphanes ; Cyclophanes ; Macrocycles ; Molecular belts ; Multistep strategy ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Belt-Shaped Molecules by a Repetitive Synthetic StrategyBelt-shaped molecules of the general type 2 containing up to five benzene ring units (cf. 37) have been synthesized by macrocyclisation reactions of ribbon-shaped precursors. An intermolecular cyclization step generates the macroheterocycles 38 and 40. The fourfold-bridged cyclophane 36 are prepared by intra-and intermolecular cyclization reactions. The X-ray structure analyses of 14, 16, 22, 23, 28, and 36 show S-shaped conformations of the molecules.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941270428
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  • 8
    Electronic Resource
    Electronic Resource
    Konkave Makroheterocyclen (1993)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 126 (1993), S. 1713-1721 
    Details
    ISSN: 0009-2940
    Keywords: Concave molecules ; Cyclophanes ; High-dilution principle ; Macrocycles ; Spheriphanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Concave MacroheterocyclesMacrocyclic compounds of the general type 2 having a spherical shape and a molecular cavity have been synthesized. A „fold and paste“-type cyclization step generates the macroheterocycles 4, 10, 11, 14, and 21. Since this approach is difficult to apply for O-substituted derivatives, the „spheriphane“ 24 was synthesized by intermolecular cyclizaiton. The X-ray structure analysis of 11 shows intermolecular interactions („dimer formation“) in the crystal.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19931260731
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  • 9
    Electronic Resource
    Electronic Resource
    Auf dem Weg zu makrocyclischen para-Phenylenen (1993)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 126 (1993), S. 1723-1732 
    Details
    ISSN: 0009-2940
    Keywords: Cyclohexanes ; Cyclohexanones ; Cyclophanes ; Macrocycles ; Paracyclophanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: On the Way to Macrocyclic para-PhenylenesStrategies are presented to synthesize the hitherto unknown [On]Paracyclophanes 1. Open chain belt-type molecules based on 1,4-connected carbocyclic six-membered rings were prepared. Functionalization of the outer rings in 4-position is the prerequisite for cyclization or lengthening of the molecular belts. In order to obtain the macrocyclic target molecules 1, well preorganized cis-isomers of 1,4-disubstituted cyclohexanes were prepared. X-ray structural analyses reveal the static stereochemistry of the intermediates 8, 9, 17, 18, and 24. The macrocyclic hydrocarbon 29 containing five cyclohexylidene units was detected.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19931260732
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  • 10
    Electronic Resource
    Electronic Resource
    Großflächige Makrocyclen aus p-Quaterphenyl-Bauteilen (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 903-907 
    Details
    ISSN: 0009-2940
    Keywords: Charge-transfer ; Kharasch coupling reaction ; Macrocycles ; Quaterphenylophane ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Flat Macrocycles Based on p-Quaterphenyl Units[1.1](3,3′″)-p-Quaterphenylophanes 1 - 3 are synthesized via 6 - 12 starting with biphenyl derivative 5. The properties of 1 - 3 (UV, NMR) and their charge-transfer complexation are compared to p-quaterphenyl. 1 - 3 are high-melting, colorless solids, which are sparingly soluble in common organic solvents. They contain two “isolated” p-quaterphenyl units. Similar to p-quaterphenyl, 2, 2a and 3 form greenish-blue chargetransfer complexes with tetracyanoethene (TCNE) in CH2Cl2.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240434
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