Binding of Porphyrins in Cyclodextrin Dimers

Venema, Fokke; Rowan, Alan E.; Nolte, Roeland J. M.

doi:10.1021/ja952401y

Cited by 122 publications

(54 citation statements)

References 7 publications

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“…The formation of such a complex was confirmed by gel chromatography experiments. [19] The 5 ± TsPP complex was eluted faster than the complexes 1 ± TsPP and 2 ± TsPP, which suggests that the former complex has a higher molecular weight, supporting the idea of the formation of a 2:2 complex.…”

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confidence: 62%

“…[19] The observed patterns indicated that the 1 ± TsPP complex has a syn structure, and the complex between 2 ± TsPP a mixed syn/anti structure. [19] From the intensity of the signals the ratio of the syn/anti conformers could be calculated to be 2:1. The geometry of the anti complex could also be deduced from the d values of the methylene spacer protons, which showed an upfield shift (broad signals at d 1 ± À 2) due to the shielding effect of the porphyrin core.…”

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confidence: 97%

“…[19] This curve had a sigmoidal shape and could not be fitted assuming simple 1:1 (CD dimer:porphyrin) complex formation. The sigmoidal shape, however, can be explained if such a 1:1 complex is formed first, followed by formation of a 2:1 (CD dimer:porphyrin) complex.…”

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confidence: 99%

“…The binding constants (K b s) of these complexes, calculated from curve fitting of the data points, are summarized in Table 5. [19] For comparison, the binding constants of complexes between the unsubstituted b-CD monomer and the two porphyrins are also given in Table 5.…”

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confidence: 99%

“…In order to study the binding geometries (syn or anti, [21] Figure 8a), of the CD dimer ± porphyrin complexes, 1 H NMR spectra of the complexes between TsPP and dimers 1 and 2 were recorded in CD 3 OD/D 2 O (1:3, v/v) at À 10 8C. [19] The observed patterns indicated that the 1 ± TsPP complex has a syn structure, and the complex between 2 ± TsPP a mixed syn/anti structure. [19] From the intensity of the signals the ratio of the syn/anti conformers could be calculated to be 2:1.…”

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confidence: 99%

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Synthesis, Conformation, and Binding Properties of Cyclodextrin Homo- and Heterodimers Connected through Their Secondary Sides

et al. 1998

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The synthesis of homo-and heterocyclodextrin (CD) dimers, containing two CD moieties that are linked through their secondary sides by aliphatic or 2,2'-bipyridyl spacers is described. In these dimers, the glucose units to which the spacers are linked have been transformed into altrose units. The dimers with an octamethylene spacer show self-complexation of the spacer in one of the CD moieties in aqueous solution, as revealed by 1 H and 13 C NMR spectroscopy. Using high-resolution (600 and 800 MHz) NMR spectroscopy and a variety of 2D NMR techniques, an assignment of nearly all of the 1 H NMR signals of two of the CD dimers was made, affording detailed information about the structure of these compounds in water. The self-inclusion of the spacers leads to lower binding affinities for ditopic guest molecules like p-toluidino-6-naphthalene sulfonate (TNS) derivatives and porphyrins. When a rigid 2,2'-bipyridyl group is used to connect the two CD moieties, self-inclusion of the spacer is not possible. This results in the formation of different complexes with ditopic guest molecules, for example, a 2:2 complex with a porphyrin. The CD heterodimers described in this paper contain an a-CD and a b-CD moiety. These dimers display site-specific binding of guest molecules.

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confidence: 62%

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confidence: 97%

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confidence: 99%

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confidence: 99%

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confidence: 99%

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Synthesis, Conformation, and Binding Properties of Cyclodextrin Homo- and Heterodimers Connected through Their Secondary Sides

et al. 1998

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Supramolekulare Elektrochemie

1998

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Welche Möglichkeiten bietet die Elektrochemie der supramolekularen Chemie? Einerseits liefert sie Informationen, die mit spektroskopischen und massenspektrometrischen Methoden nicht zugänglich sind, andererseits lassen sich mit ihr supramolekulare Wechselwirkungen beeinflussen. Rechts ist exemplarisch das Cyclovoltammogramm des gezeigten Lanthan‐Kryptats abgebildet; nur die ersten drei Reduktionen werden registriert, obwohl insgesamt sechs Elektronen auf die Bipyridineinheiten übertragen werden können (E in V gegen Ferrocen/Ferrocenium).

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