Dendritische Porphyrine: Modulation des Redoxpotentials elektroaktiver Chromophore durch periphere Multifunktionalität

Dandliker, Peter J.; Diederich, François; Gross, Maurice; Knobler, Carolyn B.; Louati, A.; Sanford, Elizabeth M.

doi:10.1002/ange.19941061713

Cited by 79 publications

(27 citation statements)

References 46 publications

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“…Unnatural amino polyacids have also been used as branching units, notably by Shinkai, [41] Fre Â -chet, [42] and Diederich. [43] The versatility of 15 was established by its use in a double exponential growth step (Scheme 5). The amino function can be deprotected with anhydrous hydrogen chloride in THF, activated wedge 17 was used as a second-generation wedge to attach to the three-directional core.…”

Section: Resultsmentioning

confidence: 99%

The Synthesis and Characterization of a New Family of Polyamide Dendrimers

et al. 1998

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A new family of dendrimers has been constructed with 5-hydroxyisophthalic acid and diethanolamine as the sources of the branching units. The design of a second-generation building block in the form of an orthogonallyprotected aminotetraacid (a single diethylphosphoramide-protected amine and four methyl-ester-protected carboxylic acid groups) has been established by a series of logical developments involving the synthesis of various dendrimer prototypes. This building block has been utilized in both convergent and divergent methods in the synthesis of monodisperse dendrimers up to the fourth generation and subsequently polydisperse sixth-generation dendrimers at the level of a mixture. One-, two-, and three-directional dendrimers of the second and fourth generation were synthesized in order to carry out detailed comparisons by GPC and by 1 H NMR spectroscopy. The GPC results suggest that the fourth-generation dendrimers adopt globular shapes, while the variable-temperature NMR spectroscopic investigations demonstrate that the periphery of the fourth-generation dendrimer is less mobile than either of its internal regions or the analogous portions of the second-generation dendrimer. Molecular modeling suggests highly globular shapes for the larger dendrimers and gives values for molecular radii in very close agreement with those obtained from analysis of the GPC results.

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Section: Resultsmentioning

confidence: 99%

The Synthesis and Characterization of a New Family of Polyamide Dendrimers

et al. 1998

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“…[49] Mit zunehmender Gröûe der Dendrimerhülle (Abb. 3 a bis 3 c) wird der Porphyrinelektrophor stärker durch die elektronenreichen, dendritischen ¾ste abgeschirmt, wodurch die Reduktionen schwieriger und die Oxidationen einfacher werden.…”

Section: Dendritische Porphyrineunclassified

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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“…[9] Because of the biological importance of porphyrins, coval- ently linked porphyrin-dendrimer hybrids have been synthesised and studied as synthetic models for globular heme proteins. [10] Experiments have established that the electrochemical properties of the porphyrin core are considerably influenced by the size and type of the dendritic environment, and complexes of the dendritically functionalised Fe II species of these systems, containing 1,2-dimethylimidazole (DiMeIm) as an axially coordinated ligand, have been investigated as model systems for T(tense)-state haemoglobin and myoglobin.…”

Section: Introductionmentioning

confidence: 99%

Self‐Assembly and Chiroptical Properties of Chiral Dendrimers Consisting of a Hamilton Receptor Substituted Porphyrin and Depsipeptide Cyanurates

2006

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The synthesis and characterisation of a new type of porphyrin-based tetrakis(Hamilton receptor) 1 is presented and the complexation of 1 with the chiral depsipeptide dendrons 7-12, with cyanuric acid functionalities as their focal points, is reported. The resulting first-to third-generation chiral supramolecular dendrimers 13-18 were characterised by NMR, UV/Vis and CD spectroscopy. Chirality transfer from the depsipeptide dendrons to the porphyrin core was demonstrated by CD spectroscopy in the case of the second-and third-generation complexes 15-18, whereas no chirality transfer and hence no diastereoselective formation of a chiral superstructure could be determined in the case of the first-generation systems. The intensities of the complexes' CD absorptions in

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Dendritische Porphyrine: Modulation des Redoxpotentials elektroaktiver Chromophore durch periphere Multifunktionalität

Cited by 79 publications

References 46 publications

The Synthesis and Characterization of a New Family of Polyamide Dendrimers

The Synthesis and Characterization of a New Family of Polyamide Dendrimers

Supramolekulare Elektrochemie

Self‐Assembly and Chiroptical Properties of Chiral Dendrimers Consisting of a Hamilton Receptor Substituted Porphyrin and Depsipeptide Cyanurates

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