Journal
SUPRAMOLECULAR CHEMISTRY
Volume 29, Issue 6, Pages 430-440Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/10610278.2016.1265120
Keywords
Mechanically interlocked molecules; pillar[5] arene; cyclotriveratrylene
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Funding
- The Leverhulme Trust [RPG-2014-148]
- EPSRC [EP/K039202/1]
- EPSRC and Charles Brotherton Trust for studentship support
- Diamond Light Source [MT-10334]
- Engineering and Physical Sciences Research Council [EP/K039202/1] Funding Source: researchfish
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A series of [4]pseudorotaxanes composed of three-way axle threads based on the cyclotriguaiacylene family of crown-shaped cavitands and three threaded macrocyclic components has been achieved. These exploit the strong affinity for electron-poor alkyl-pyridinium units to reside within the electron-rich cavity of macrocycles, in this case dimethoxypillar[5]arene (DMP). The branched [4]pseudorotaxane assemblies {(DMP)(3)center dot L}(3+) ,where L = N-alkylated derivatives of the host molecule (+/-)-tris-(isonicotinoyl)cyclotriguaiacylene, were characterised by NMR spectroscopy and mass spectrometry, and an energy-minimised structure of {(DMP)(3)center dot(tris-(N-propyl-isonicotinoyl)cyclotriguaiacylene)}(3+) was calculated. Crystal structures of N-ethyl-isonicotinoyl) cyclotriguaiacylene hexafluorophosphate and N-propyl-isonicotinoyl)cyclotriguaiacylene hexafluorophosphate each show 'hand-shake' self-inclusion motifs occurring between the individual cavitands. [GRAPHICS]
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