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  • 1
    ISSN: 1434-193X
    Keywords: Cyclophanes ; Molecular recognition ; Molecular shuttles ; Rotaxanes ; Template-directed synthesis ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---Two dumbbell-shaped compounds (8 and 11), each composed of two polyether chains intercepted by a 1,4-dioxybenzene recognition site, terminated by tetraarylmethane-based stoppers, and emanating from a central 9,10- or a 2,6-dioxyanthracene unit, have been synthesized. Two [2]rotaxanes (9 · 4 PF6 and 12 · 4 PF6) have been prepared by interlocking these dumbbell-shaped compounds (8 and 11) with a bipyridinium-based tetracationic cyclophane (15 · 4 PF6) - namely, cyclobis(paraquat-p-phenylene). A [3]rotaxane (10 · 8 PF6) incorporating two cyclophane components (15 · 4 PF6) was also obtained when the 9,10-dioxyanthracene-containing dumbbell-shaped compound (8) incorporating two 1,4-dioxybenzene recognition sites was employed. The 1H-NMR spectroscopic investigation of the [2]rotaxanes (9 · 4 PF6 and 12 · 4PF6) revealed that the cyclophane component encircles one of the two 1,4-dioxybenzene recognition sites in the 9,10-dioxyanthracene-containing [2]rotaxane (9 · 4 PF6) and the 2,6-dioxyanthracene unit in the other [2]rotaxane (12 · 4 PF6). These structures have been confirmed by UV/Vis and electrochemical experiments. Comparison with the spectroscopic properties of simple model compounds shows the presence of electronic interactions which lead to (i) the occurrence of very efficient energy transfer processes in the dumbbell-shaped components and (ii) perturbations in the absorption spectra with appearance of two charge-transfer absorption bands and complete luminescence quenching in the [2]rotaxanes. For the 2,6-dioxyanthracene-containing [2]rotaxane (12 · 4 PF6), it has been demonstrated that the cyclophane can be displaced from the dioxyanthracene to the 1,4-dioxybenzene station upon electrochemical oxidation.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 1434-193X
    Keywords: Catenanes ; Cyclophanes ; Electrochemistry ; Electronic spectroscopy ; Template-directed synthesis ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Catenanes composed of two, three, five, or seven interlocked macrocycles have been synthesized in yields ranging from 1 to 30%. Their template-directed syntheses rely on a series of cooperative noncovalent bonding interactions between π-electron rich 1,5-dioxynaphthalene ring systems and π-electron deficient bipyridinium units which are incorporated within the macrocyclic components. The interlocked structure associated with one of the [3]catenanes was demonstrated unequivocally by single crystal X-ray analysis which also revealed the formation of polar stacks stabilized by intermolecular [π···π] interactions. The number of interlocked components of each catenane was determined by liquid secondary ion, matrix-assisted laser desorption ionization/time-of-flight, and/or electrospray mass spectrometries. The absorption spectra, emission spectra, and electrochemical properties of the macrocyclic components and of the catenanes have been investigated. Two kinds of charge-transfer absorption bands (intramolecular in the cyclophanes containing electron-donor and electron-acceptor units, intercomponent in the catenanes) have been found. Such charge-transfer excited states are responsible for the quenching of the potentially fluorescence units of the cyclophanes, and of the crown ethers in the catenanes. Charge-transfer electronic interactions are also evidenced by the electrochemical behavior. Correlations among the redox potentials of the various compounds are reported and discussed.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
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