Literature DB >> 18759481

Efficient potassium-ion-templated synthesis and controlled destruction of [2]rotaxanes based on cascade complexes.

Tao Han1, Chuan-Feng Chen.   

Abstract

The triptycene-based macrotricyclic host can form pseudorotaxane-like cascade complexes with anthraquinone and its tetra-azide terminally functionalized derivative in the presence of potassium ions, which subsequently resulted in the synthesis of three novel potassium-ion-templated [2]rotaxanes 10-12 in high yields by the "threading followed by stoppering" approach. Since the potassium ions act not only as templates during the stoppering reactions but also as nonslipping chocks to shrink the inner diameter of the wheel cavity, the deslipping behaviors of the [2]rotaxanes with different triazole stoppers by peeling off the potassium ions with 18-crown-6 were further investigated. The results show that rotaxanes 10 and 11 can be destroyed, but under the same conditions the dumbbell and ring components of rotaxane 12 remain interlocked.

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Year:  2008        PMID: 18759481     DOI: 10.1021/jo801522f

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  3 in total

1.  Multistimuli Sensitive Behavior of Novel Bodipy-Involved Pillar[5]arene-Based Fluorescent [2]Rotaxane and Its Supramolecular Gel.

Authors:  Nana Sun; Xin Xiao; Wenjun Li; Jianzhuang Jiang
Journal:  Adv Sci (Weinh)       Date:  2015-05-26       Impact factor: 16.806

2.  Relative contractile motion of the rings in a switchable palindromic [3]rotaxane in aqueous solution driven by radical-pairing interactions.

Authors:  Leah S Witus; Karel J Hartlieb; Yuping Wang; Aleksandrs Prokofjevs; Marco Frasconi; Jonathan C Barnes; Edward J Dale; Albert C Fahrenbach; J Fraser Stoddart
Journal:  Org Biomol Chem       Date:  2014-08-28       Impact factor: 3.876

3.  A K+-promoted Diels-Alder reaction by using a self-assembled macrocyclic boronic ester containing two crown ether moieties.

Authors:  Kosuke Ono; Morikazu Niibe; Nobuharu Iwasawa
Journal:  Chem Sci       Date:  2019-07-03       Impact factor: 9.825

  3 in total

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