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

preprint
submitted on 22.11.2018, 23:05 and posted on 23.11.2018, 16:35 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.

Funding

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)

History

Email Address of Submitting Author

tomislav.friscic@mcgill.ca

Institution

McGill University

Country

Canada

ORCID For Submitting Author

0000-0002-3921-7915

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

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