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DOI:
https://doi.org/10.34804/supra.20210928192 Cc Cc by 4.0
Title:
Molecular-Recognition Properties of a Water-Soluble Cucurbit[6]uril Analogue
https://pubs.acs.org/na101/home/literatum/publisher/achs/journals/content/joceah/2006/joceah.2006.71.issue-3/jo052294i/production/images/large/jo052294in00001.jpeg
Description:
The molecular-recognition properties of the cucurbit[6]uril analogue (1) in aqueous buffer (sodium acetate, 50 mM, pH 4.74, 25 °C) toward a variety of guests including alkanediamines (6−12), aromatics (14−32), amino acids (33−36), and nucleobases (37−42) were studied by fluorescence spectroscopy. For the alkanediamines studied (H2N(CH)nNH2, n = 6, 7, 8, 9, 10, 11, 12), the association constants increase as the length of the alkane (n) is increased. Host 1 is capable of forming strong complexes with guests containing aromatic rings with association constants (Ka) ranging from 102 to 106 M-1 as a result of the favorable π−π interactions that occur between host 1 and the aromatic rings of the guest when bound in the cavity of 1. Biologically relevant guests such as amino acids and nucleobases are also bound in the cavity of 1 with Ka values ranging from 103 to 106 M-1. Consequently, cucurbit[6]uril analogue 1 functions as a versatile fluorescent sensor for the presence of a wide range of chemically and biologically important substances in aqueous solution including nitroaromatics, neurotransmitters, amino acids, and nucleobases.
Citation:

L. Isaacs, J. Lagona, B. D. Wagner, SupraBank 2024, Molecular-Recognition Properties of a Water-Soluble Cucurbit[6]uril Analogue (dataset). https://doi.org/10.34804/supra.20210928192

Link: https://doi.org/10.34804/supra.20210928192
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Citation:

J. Lagona, B. D. Wagner, L. Isaacs, J. Org. Chem. 2006, 71, 1181–1190.

Link: https://doi.org/10.1021/jo052294i
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Creators:
Orcidid | Ror | Jason Lagona
Orcidid | Ror | Brian D. Wagner
Orcidid | Ror | Lyle Isaacs
Contributers:
Orcidid | Ror | Rui Kang | DataManager

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