Synthesis and Recognition Properties of Cucurbit[8]uril Derivatives
Brittany Vinciguerra1, Peter Y Zavalij1, Lyle Isaacs1
1Department of Chemistry and Biochemistry, University of Maryland , College Park, Maryland 20742, United States.
Abstract:
A building block approach to the synthesis of Me4CB[8] and Cy2CB[8] by condensation of glycoluril hexamer 1 with bis(cyclic ethers) 2 is reported. X-ray crystallography demonstrates that the equatorial substitution results in an ellipsoidal cavity. Me4CB[8] and Cy2CB[8] display enhanced aqueous solubility and retain the ability to bind to guests (3-9) typical of unsubstituted CB[8]. The higher inherent solubility of Me4CB[8] allowed it to be used as a solubilizing excipient for insoluble drugs.
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