Effect of Substituents on the Formation of Pseudorotaxanes from Dialkylammonium Ions and Dibenzo-24-crown-8

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10.

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[2]Pseudorotaxane formation between rigid Y-shaped 2,4,5-triphenylimidazolium axles and [24]crown-8 ether wheels.

A new templating motif for the formation of [2]pseudorotaxanes is described in which rigid, Y-shaped axles with an imidazolium core and aromatic substituents at the 2-, 4- and 5-positions interact with [24]crown-8 ether wheels ([24]crown-8 and dibenzo[24]crown-8). The Y-shape of the axle significantly enhances the association between axle and wheel when compared to simple imidazolium cations.

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"Three methylene spacer" bis(benzimidazolium) derivatives act as a new template for threading dibenzo-24-crown-8 into [2]pseudorotaxanes. In this Article we sought to unveil the difference in the extent of threading of various "three methylene spacer" bis-benzimidazolium moieties based on differences in aromatic methyl substituent positions and anions through the macrocycle dibenzo-24-crown-8. ...

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A chromophoric switch based on pseudorotaxanes.

In a three-component system containing dibenzo-24-crown-8 (1), diamino-dibenzo-24-crown-8 (2), and 1,2-bis(4,4(')-dipyridyl)ethane (3(2+)), axle 3(2+) can shuttle between wheels 1 and 2 by acid-base control, accompanying color changes from yellow to red. This system could not only be taken as a chromophoric supramolecular switch, but also exhibit a function as INHIBIT logic gate.

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تاریخ انتشار 1999