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DOI:
https://doi.org/10.34804/supra.20210928388 Cc Cc by 4.0

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

https://pubs.acs.org/na101/home/literatum/publisher/achs/journals/content/jacsat/2005/jacsat.2005.127.issue-45/ja055013x/production/images/large/ja055013xn00001.jpeg

Description:
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 homologuesCB[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 1012 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 107, 106, 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.

Citation:

L. Isaacs, P. Y. Zavalij, S. Liu, P. Mukhopadhyay, C. Ruspic, S. Chakrabarti, SupraBank 2025, The Cucurbit[n]uril Family:  Prime Components for Self-Sorting Systems (dataset). https://doi.org/10.34804/supra.20210928388

Link: https://doi.org/10.34804/supra.20210928388
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Citation:

S. Liu, C. Ruspic, P. Mukhopadhyay, S. Chakrabarti, P. Y. Zavalij, L. Isaacs, J. Am. Chem. Soc. 2005, 127, 15959–15967.

Link: https://doi.org/10.1021/ja055013x
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Creators:
Orcidid | Ror | Simin Liu
Orcidid | Ror | Christian Ruspic
Orcidid | Ror | Pritam Mukhopadhyay
Orcidid | Ror | Sriparna Chakrabarti
Orcidid | Ror | Peter Y. Zavalij
Orcidid | Ror | Lyle Isaacs

Contributers:
Orcidid | Ror | Anxhela Zhiti | DataManager
Orcidid | Ror | Katharina Wendler | DataManager

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