Glycylglycin‐Rotaxane — Wasserstoffbrückenvermittelte Selbstorganisation synthetischer Peptid‐Rotaxane

Leigh, David A.; Murphy, Aden; Smart, John P.; Slawin, Alexandra M. Z.

doi:10.1002/ange.19971090711

Cited by 62 publications

(17 citation statements)

References 38 publications

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“…[375] Signifikante Mengen des Produkts 66 (29 %) wurden in der Reaktion zwischen 60 b und Isophthaloyldichlorid durch die Bildung starker H-Brücken zwischen dem leeren Makrocyclus 61 b und seiner linearen Vorstufe gebildet (Schema 34). [379,380] Auûerdem berichtete diese Gruppe, dass lineare Amide [381] oder Peptide [382] ebenfalls als Template in der Synthese von auf Amiden basierenden Rotaxanen wie 67 fungieren können, wobei die Ausbeuten bis zu 62 % betragen (Schema 34). [378] Später fanden Leigh und Mitarbeiter ähnliche Templateffekte bei der Bildung von Catenanen aus Isophthaloyldichlorid und Benzyldiaminen.…”

Section: Bildung Von Catenanen Und Rotaxanenunclassified

Nichtkovalente Synthese mit Wasserstoffbrücken

2001

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Section: Bildung Von Catenanen Und Rotaxanenunclassified

Nichtkovalente Synthese mit Wasserstoffbrücken

2001

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“…These conditions are favorable for the hydrogen-bond recognition between macrocycle and thread in construction mechanical interlocked molecules. [13] Recently, examples of a click-reaction-based synthesis of rotaxanes and catenanes have been reported. [14] The molecular rotaxane and muscle developed by Busseron et al also showed that the triazolium cation could be recognized by dibenzo- [24]crown-8.…”

Section: Introductionmentioning

confidence: 99%

A Dual‐Response [2]Rotaxane Based on a 1,2,3‐Triazole Ring as a Novel Recognition Station

Zheng

Zhou

et al. 2009

Chemistry A European J

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Two novel multilevel switchable [2]rotaxanes containing an ammonium and a triazole station have been constructed by a Cu(I)-catalyzed azide-alkyne cycloaddition reaction. The macrocycle of [2]rotaxane containing a C6-chain bridge between the two hydrogen bonding stations exhibits high selectivity for the ammonium cation in the protonated form. Interestingly, the macrocycle is able to interact with the two recognition stations when the bridge between them is shortened. Upon deprotonation of both [2]rotaxanes, the macrocycle moves towards the triazole recognition site due to the hydrogen-bond interaction between the triazole nitrogen atoms and the amide groups in the macrocycle. Upon addition of chloride anion, the conformation of [2]rotaxane is changed because of the cooperative recognition of the chloride anion by a favorable hydrogen-bond donor from both the macrocycle isophthalamide and thread triazole CH proton.

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“…The reaction of thread 1 with dodecyl iodide [30] in DMSO yields fulleropyrrolidinium salt 4 (Scheme 1). Conversely, when rotaxane 2 was allowed to react with an excess of dodecyl iodide (3,27 and 45 equivalents) in DMSO, only rotaxane 3 was obtained after chromatographic purification and the formation of the corresponding trialA C H T U N G T R E N N U N G kylA C H T U N G T R E N N U N G ation by-product was not detected.…”

Section: Resultsmentioning

confidence: 99%

A Molecular Shuttle Driven by Fullerene Radical‐Anion Recognition

Scarel

Valenti

Gaikwad

et al. 2012

Chemistry A European J

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We describe a electrochemically driven molecular shuttle, in which shuttling takes place by means of fullerene radical-anion recognition that results in a very low operation potential (E(1/2) =-0.580 V vs. decamethylferrocene). This has been achieved by introducing positive charges on the macrocycle, which strengthen the existing π-π interactions between the macrocycle and the electrogenerated fullerene radical anion by means of an electrostatic component. In addition, the synthesis of such a molecular shuttle has been accomplished by developing a new synthetic approach that exploits the controlled translocation of the macrocycle as a selective protecting group.

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Glycylglycin‐Rotaxane — Wasserstoffbrückenvermittelte Selbstorganisation synthetischer Peptid‐Rotaxane

Cited by 62 publications

References 38 publications

Nichtkovalente Synthese mit Wasserstoffbrücken

Nichtkovalente Synthese mit Wasserstoffbrücken

A Dual‐Response [2]Rotaxane Based on a 1,2,3‐Triazole Ring as a Novel Recognition Station

A Molecular Shuttle Driven by Fullerene Radical‐Anion Recognition

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