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Tris - N -alkylpyridinium-functionalised cyclotriguaiacylene hosts as axles in branched [4]pseudorotaxane formation

DOI: 10.1080/10610278.2016.1265120 DOI Help

Authors: Flora Thorp-greenwood (University of Leeds) , Alexander D. Brennan (University of Leeds) , Samuel Oldknow (University of Leeds) , James J. Henkelis (University of Leeds) , Katie J. Simmons (University of Leeds) , Colin W. G. Fishwick (University of Leeds) , Michaele J. Hardie (University of Leeds)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Supramolecular Chemistry , VOL 29 , PAGES 430 - 440

State: Published (Approved)
Published: March 2017
Diamond Proposal Number(s): 10334

Abstract: 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∙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∙(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.

Subject Areas: Chemistry

Instruments: I19-Small Molecule Single Crystal Diffraction