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Chiral guest, dibenzyl 4,4\u2032\u2010diacetoxy\u20106,6\u2032\u2010dimethyl\u2010[1,1\u2032\u2010biphenyl]\u20102,2\u2032\u2010dicarboxylate (<jats:bold>3<\/jats:bold>) was encapsulated within the dissymmetric cavity of <jats:bold>2\u2009a<\/jats:bold>(BF<jats:sub>4<\/jats:sub>)<jats:sub>4<\/jats:sub>, resulting in a high diastereoselectivity of &gt;99\u2009% <jats:italic>de<\/jats:italic>. The encapsulated guest was successfully removed from the complex without racemization through precipitation of the empty capsule. CD spectra confirmed that the chirality of the capsule was maintained in THF and 1,4\u2010dioxane for long periods, whereas a small amount of acetonitrile accelerated racemization of the empty capsule. The activation parameters of the racemization reaction were determined in dichloromethane and 1,2\u2010dichloroethane, resulting in positive enthalpic contributions and large negative entropic contributions, respectively. Accordingly, the racemization fits a first\u2010order kinetic model. Mechanically coupled Cu<jats:sup>+<\/jats:sup>\u20102,2\u2032\u2010bipyridine coordination centers were responsible for the high\u2010energy barrier of racemization and led to the unique chiral memory of the dissymmetric cavity, which was turned off by the addition of acetonitrile.<\/jats:p>","DOI":"10.1002\/chem.201505183","type":"journal-article","created":{"date-parts":[[2015,12,29]],"date-time":"2015-12-29T05:34:49Z","timestamp":1451367289000},"page":"3250-3254","source":"Crossref","is-referenced-by-count":42,"title":["Frozen Dissymmetric Cavities in Resorcinarene\u2010Based Coordination Capsules"],"prefix":"10.1002","volume":"22","author":[{"given":"Taisuke","family":"Imamura","sequence":"first","affiliation":[{"name":"Department of Chemistry Graduate School of Science Hiroshima University  1-3-1 Kagamiyama Higashi-Hiroshima Hiroshima 739-8526 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