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The Inverted Cucurbit[n]uril Family

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posted on 28.12.2005, 00:00 by Lyle Isaacs, Sang-Kyu Park, Simin Liu, Young Ho Ko, Narayanan Selvapalam, Youngkook Kim, Hyunuk Kim, Peter Y. Zavalij, Ghyung-Hwa Kim, Heung-Soo Lee, Kimoon Kim
We report the isolation, characterization, and recognition behavior of iCB[6] and iCB[7], which are diastereomers of CB[6] and CB[7], respectively, containing a single inverted glycoluril unit. Product resubmission experiments establish that these inverted CB[n] are intermediates in the mechanism of CB[n] formation. As a consequence of the inverted glycoluril ring, these inverted cucurbiturils possess a permanent dipole moment, are slightly smaller than their diastereomers, show distinctive selectivity in their recognition behavior, and report directly on the contents of their hydrophobic cavity.