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

DOI:: https://doi.org/10.34804/supra.20210928388
Title:: The Cucurbit[n]uril Family: Prime Components for Self-Sorting Systems

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.

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Creators:: | | Simin Liu; | | Christian Ruspic; | | Pritam Mukhopadhyay; | | Sriparna Chakrabarti; | | Peter Y. Zavalij; | | Lyle Isaacs
Contributers:: | | Anxhela Zhiti | DataManager; | | Katharina Wendler | DataManager

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Citation:	L. Isaacs, P. Y. Zavalij, S. Liu, P. Mukhopadhyay, C. Ruspic, S. Chakrabarti, SupraBank 2026, 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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