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Issue 44, 2018
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[3]rotaxanes composed of two dibenzo-24-crown-8 ether wheels and an azamacrocyclic complex

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Abstract

The azamacrocyclic complex was used as a platform for the construction of [3]rotaxanes containing two DB24C8 macrocycles per molecule. The complex unit incorporates two electron deficient π-bond systems and two N–H hydrogen bond donating groups which facilitated the formation of a 1 : 2 interlocked structure. Synthesis and properties of such compounds are presented. Structures of the obtained compounds were confirmed by NMR spectroscopy, ESI mass spectrometry, elemental analysis and single crystal X-ray diffraction. Both [3]rotaxanes containing two DB24C8 macrocycles per molecule crystallise in P[1 with combining macron] and P21/n space groups. They have different counterions (PF6 and Cl anions, respectively) and mostly disordered solvent molecules such as water, methanol and acetone. Both [3]rotaxanes have a flexible axle in which the Cl salt takes the shape closer to the “S”-letter, while in the PF6 case the axle is more linear. The shape results from respective packing and intra-, and intermolecular interactions among the moieties in the rotaxane and the crystal lattice.

Graphical abstract: [3]rotaxanes composed of two dibenzo-24-crown-8 ether wheels and an azamacrocyclic complex

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Supplementary files

Article information


Submitted
07 Aug 2018
Accepted
09 Oct 2018
First published
11 Oct 2018

Dalton Trans., 2018,47, 15845-15856
Article type
Paper

[3]rotaxanes composed of two dibenzo-24-crown-8 ether wheels and an azamacrocyclic complex

M. Woźny, A. Więckowska, D. Trzybiński, S. Sutuła, S. Domagała and K. Woźniak, Dalton Trans., 2018, 47, 15845
DOI: 10.1039/C8DT03225D

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