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Size-Control by Anion Templating in Mechanochemical Synthesis of Hemicucurbiturils in the Solid State

submitted on 22.11.2018 and posted on 23.11.2018 by Sandra Kaabel, Robin Stein, Maria Fomitšenko, Ivar Järving, Tomislav Friscic, Riina Aav
Self-organization is one of the most intriguing phenomena of chemical matter. While the self-assembly of macrocycles and cages in dilute solution has been extensively studied, it remains poorly understood in solvent-free environments. Here, we provide the first example of using anionic templates to achieve selective assembly of differently sized macrocycles in a solvent-free system. Using the acid-catalyzed synthesis of cyclohexanohemicucurbiturils as a model system, we demonstrate size-controlled quantitative synthesis of 6- or 8-membered macrocycles, taking place through spontaneous anion-directed re-organization of mechanochemically-obtained oligomers in the solid state.


Estonian Ministry of Education and Research (Grant Nos. IUT 19-32, PUT692)

Centre of Excellence in Molecular Cell Engineering (2014-2020.4.01.15-0013)

European Regional Development Fund Dora Pluss

National Science and Engineering Research Council (NSERC) Discovery Grant (RGPIN-2017-06467)

National Science and Engineering Research Council (NSERC) E. W. R. Steacie Memorial Fund (NSERC SMFSU 507347-17)


Email Address of Submitting Author


McGill University



ORCID For Submitting Author


Declaration of Conflict of Interest

Authors declare there are no conflicts of interest

Version Notes

This is version 1 of the manuscript and supplementary information