Aggregation Behavior of Cyclodextrin-Based [3]Rotaxanes.

Chemistry

Institute for Chemical Technology and Polymer Chemistry (ITCP), Karlsruhe Institute of Technology (KIT), 76131, Karlsruhe, Germany.

Published: September 2023

The aggregation of a cyclodextrin (CD)-based [3]rotaxane has been observed and analyzed in detail for the first time in this work. Although the hexagonal packing aggregation of CD-based polyrotaxane is a well known phenomenon, corresponding studies in terms of rotaxanes without any polymer structure have not been conducted so far, probably owing to the difficulty of the molecular design. We synthesized a series of [3]rotaxane species by using a urea-end-capping method and evaluated their aggregation behavior by XRD and SEM measurements. [3]Rotaxane species containing native CD rings showed clear signals assigned to the hexagonal packing by XRD measurement as did polyrotaxane; this proved their aggregation capability. Because the corresponding per-acetylated derivatives did not show this aggregation behavior, the driving force of this aggregation was suggested to be hydrogen bond formation among CD units. The effect of axle end structures and partial acetylation of CDs were also studied.

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Source
http://dx.doi.org/10.1002/chem.202301582DOI Listing

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