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Cited by 854

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The Cucurbit[n]uril Family: Prime Components for Self-Sorting Systems

Liu, Simin, Ruspic, Christian, Mukhopadhyay, Pritam, Chakrabarti, Sriparna, Zavalij, Peter Y., Isaacs, Lyle·2005·Journal of the American Chemical Society

Abstract

We determined the values of Ka for a wide range of host-guest complexes of cucurbit[n]uril (CB[n]), where n = 6-8, using 1H NMR competition experiments referenced to absolute binding constants measured by UV/vis titration. We find that the larger homologues--CB[7] and CB[8]--individually maintain the size, shape, and functional group selectivity that typifies the recognition behavior of CB[6]. The cavity of CB[7] is found to effectively host trimethylsilyl groups. Remarkably, the values of Ka for the interaction of CB[7] with adamantane derivatives 22-24 exceeds 10(12) M(-1)! The high levels of selectivity observed for each CB[n] individually is also observed for the CB[n] family collectively. That is, the selectivities of CB[6], CB[7], and CB[8] toward a common guest can be remarkably large. For example, guests 1, 3, and 11 prefer CB[8] relative to CB[7] by factors greater than 10(7), 10(6), and 3000, respectively. Conversely, guests 23 and 24 prefer CB[7] relative to CB[8] by factors greater than 5100 and 990, respectively. The high levels of selectivity observed individually and collectively for the CB[n] family renders them prime components for the preparation of functional biomimetic self-sorting systems.

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Metadata

Authors
Liu, S., Ruspic, C., Mukhopadhyay, P., Chakrabarti, S., Zavalij, P. Y., & Isaacs, L.
Venue
Journal of the American Chemical Society
Published
2005-10-21
Volume
127
Issue
45
Pages
15959-15967
ISSN
  • 0002-7863 (ISSN-L)
  • 1520-5126
OpenAlex
W2091068412
Cited by
854
References
7
FWCI
14.09
Type
journal article
Language
en
Open access
closed

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CoChat. (2026). Citation check: The Cucurbit[n]uril Family: Prime Components for Self-Sorting Systems. https://app.cochat.ai/papers/10.1021/ja055013x
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Liu, S., Ruspic, C., Mukhopadhyay, P., Chakrabarti, S., Zavalij, P. Y., & Isaacs, L. (2005). The Cucurbit[n]uril Family: Prime Components for Self-Sorting Systems. Journal of the American Chemical Society. https://doi.org/10.1021/ja055013x

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