Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 23, Pages 8800-8806Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo061516p
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Fine and/or drastic tuning of capsule space has been attained by alteration of the hydrogen-bonding linker and/or hemispherical cavitand, respectively. Two molecules of tetracarboxyl-cavitand 1 or tetrakis-(4-carboxyphenyl)-cavitand 2 as a hemisphere and four molecules of 2-aminopyrimidine (2-AP) or tetrahydro-2-pyrimidinone (THP) as an equatorial hydrogen-bonding linker self-assemble into a capsule [(1)(2)center dot(2-AP)(4)] (3), [(1)(2)center dot(THP)(4)] (4), [(2)(2)center dot(2-AP)(4)] (5), or [(2)(2)center dot(THP)(4)] (6), respectively, via 16 hydrogen bonds. These capsules provide isolated nanospace and can encapsulate one guest molecule (7-13) in solution. Each capsule has a different cavity size and shows particular guest selectivity on the competitive encapsulation experiments.
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