Aufbau des ersten Fulleren‐haltigen [2]Catenans durch Selbstorganisation

Ashton, Peter R.; Diederich, François; Gómez-López, Marcos; Nierengarten, Jean‐François; Preece, Jon A.; Raymo, Françisco M.; Stoddart, J. Fraser

doi:10.1002/ange.19971091352

Cited by 19 publications

(10 citation statements)

References 45 publications

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“…[14] In addition Diederich, Stoddart,et al prepared a [60]fullerene-containing [2]catenane that includes a trans-4 bisadduct as a building block, based on the charge-transfer (CT) interaction between the p-electron-deficient cyclobis(paraquat-p-phenylene) and the p-electron-rich 1,4-dialkoxybenzene moieties. [15] To the best of our knowledge, this is the only example of a [60]fullerene-based [2]catenane, and there has been no report of [2]catenanes to date, in which the electron-accepting ability of [60]fullerene is directly involved.…”

Section: Dedicated To Professor Emeritus Dr Soichi Misumi On the Occmentioning

confidence: 94%

“…The introduction of [60]fullerene into these systems promises further enhancement of the functionality of such molecular assemblies because of its unique electronic properties, especially as a strong electron acceptor. [13] However, examples that incorporate [60]fullerene into rotaxanes and catenanes, [14][15][16] which have been constructed by independent synthetic methodologies, are extremely limited. Diederich,Sauvage,et al have prepared a [2]rotaxane that possesses two fullerene stoppers at the ends of its threadlike component, which takes advantage of the coordination of Cu + ions by 1,10-phenanthroline ligands.…”

Section: Dedicated To Professor Emeritus Dr Soichi Misumi On the Occmentioning

confidence: 99%

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Preparation of Neutral [60]Fullerene‐Based [2]Catenanes and [2]Rotaxanes Bearing an Electron‐Deficient Aromatic Diimide Moiety

et al. 2003

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Section: Dedicated To Professor Emeritus Dr Soichi Misumi On the Occmentioning

confidence: 94%

Section: Dedicated To Professor Emeritus Dr Soichi Misumi On the Occmentioning

confidence: 99%

Preparation of Neutral [60]Fullerene‐Based [2]Catenanes and [2]Rotaxanes Bearing an Electron‐Deficient Aromatic Diimide Moiety

et al. 2003

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“…With the exception of cis-1, all possible bis-addition patterns (Scheme 7-1) have been obtained today and some interesting examples (42-54) [25,59,60,[64][65][66][67][68] for the various functionalization patterns are presented in Scheme 7-8.…”

Section: The Bingel Macrocyclizationmentioning

confidence: 99%

“…This was exploited in the construction of the &,-containing catenane (+)-67 -4PF6 starting from the trans4 crown ether (+48 [65]. The formation of (+)-67.…”

Section: Other Bis-functionalization Patternsmentioning

confidence: 99%

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Regio‐ and Stereoselective Multiple Functionalization of Fullerenes

Diederich

Kessinger

1999

Templated Organic Synthesis

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The synthesis of multiple adducts of CW has attracted much attention in recent years [ 11.Investigations of covalent derivatives with varying degrees and patterns of addition make it possible to explore how characteristic fullerene properties are affected by functionalization-induced changes in the conjugated n-chromophore [2]. Furthermore, higher adducts of c 6 0 represent an unprecedented family of three-dimensional building blocks for molecular scaffolding targeting advanced fullerene materials and technologies [3]. The direct sequential multiple functionalization of the carbon sphere, however, is problematic in most cases, and isolation of a pure higher adduct usually requires tedious chromatographic isomer separation [4-61. Moreover, a great diversity of interesting addition patterns is not accessible by sequential derivatization. Therefore, we proposed in 1994 a more general approach to the regioselective formation of multiple adducts of c 6 0 by taking advantage of tether-directed remote functionalization techniques [7]. Such strategies had been initially developed by Breslow and co-workers for the selective functionalization of steroids and long-chain alkanes (see Chapter 6 ) [8]. Here, we illustrate how the application of non-covalent and covalent templates provides access to a great diversity of three-dimensionally functionalized fullerene building blocks. Templated synthesis now serves as a powerful tool for chemists interested in exploiting the outstanding technological potential of fullerenes and their covalent derivatives. Anthracenes as Reversible Covalent TemplatesAmong the most versatile reactions in fullerene chemistry is the Bingel cyclopropanation with 2-bromomalonate in the presence of base [9]. The problematics of regioisomeric product formation in nucleophilic additions to C,, is illustrated in the following, using this reaction as an example. By sequential double Bingel addition, Hirsch and co-workers obtained seven (1-7) out of eight possible bis-adducts named as cis-1-3, eface and edge (these two bis-adducts are identical if the two addends are identical), and truns-I -4 (Scheme 7-1) [lo, 111, which could be separated by high-performance liquid chromatography (HPLC). Only the cis-1 bis-adduct was not formed in detectable quantities due to steric interactions between the addends which are forced into close proximity. The e (3) and trans-3 (5) bis-adducts are the major products in the sequential double addition,

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PtII-gesteuerte Selbstorganisation eines zweikernigen, Fulleren-haltigen Cyclophans

Habicher

Nierengarten

Gramlich³

et al. 1998

Angewandte Chemie

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Die Selbstorganisation zweier C60‐Hexakisaddukte, die je eine Di(4‐pyridyl)methanogruppe tragen, mit zwei PtII‐Zentren führte zum zweikernigen Metallacyclophan 1 als erstem Repräsentanten einer neuen Klasse supramolekularer Multifullerenverbindungen. Der Röntgenstrukturanalyse von 1 zufolge bilden die beiden PtII‐Zentren und die beiden quartären C‐Atome der Dipyridylmethanogruppen auf Kosten beträchtlicher Winkelspannung ein perfekt planares Parallelogram.

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Aufbau des ersten Fulleren‐haltigen [2]Catenans durch Selbstorganisation

Cited by 19 publications

References 45 publications

Preparation of Neutral [60]Fullerene‐Based [2]Catenanes and [2]Rotaxanes Bearing an Electron‐Deficient Aromatic Diimide Moiety

Preparation of Neutral [60]Fullerene‐Based [2]Catenanes and [2]Rotaxanes Bearing an Electron‐Deficient Aromatic Diimide Moiety

Regio‐ and Stereoselective Multiple Functionalization of Fullerenes

PtII-gesteuerte Selbstorganisation eines zweikernigen, Fulleren-haltigen Cyclophans

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