The Inverted Cucurbit[n]uril Family

作者: Lyle Isaacs , Sang-Kyu Park , Simin Liu , Young Ho Ko , Narayanan Selvapalam

DOI: 10.1021/JA056988K

关键词: Molecular recognitionCucurbiturilInclusion compoundMoleculeStereochemistryDiastereomerChemistrySelectivityGlycolurilRing (chemistry)

摘要: We report the isolation, characterization, and recognition behavior of iCB[6] iCB[7], which are diastereomers CB[6] CB[7], respectively, containing a single inverted glycoluril unit. Product resubmission experiments establish that these CB[n] intermediates in mechanism formation. As consequence ring, cucurbiturils possess permanent dipole moment, slightly smaller than their diastereomers, show distinctive selectivity behavior, directly on contents hydrophobic cavity.

参考文章(6)
Brian D. Wagner, Patricia G. Boland, Jason Lagona, Lyle Isaacs, A cucurbit[6]uril analogue: host properties monitored by fluorescence spectroscopy. Journal of Physical Chemistry B. ,vol. 109, pp. 7686- 7691 ,(2005) , 10.1021/JP044369C
Arindam Chakraborty, Anxin Wu, Dariusz Witt, Jason Lagona, James C. Fettinger, Lyle Isaacs, Diastereoselective formation of glycoluril dimers: isomerization mechanism and implications for cucurbit[n]uril synthesis. Journal of the American Chemical Society. ,vol. 124, pp. 8297- 8306 ,(2002) , 10.1021/JA025876F
Hiroyuki Isobe, Sota Sato, Eiichi Nakamura, Synthesis of disubstituted cucurbit[6]uril and its rotaxane derivative. Organic Letters. ,vol. 4, pp. 1287- 1289 ,(2002) , 10.1021/OL025749O
Jason Lagona, Pritam Mukhopadhyay, Sriparna Chakrabarti, Lyle Isaacs, The cucurbit[n]uril family Angewandte Chemie. ,vol. 44, pp. 4844- 4870 ,(2005) , 10.1002/ANIE.200460675
Christian Lettmann, Heike Hinrichs, Wilhelm F. Maier, Combinatorial Discovery of New Photocatalysts for Water Purification with Visible Light Angewandte Chemie International Edition. ,vol. 40, pp. 3160- 3164 ,(2001) , 10.1002/1521-3773(20010903)40:17<3160::AID-ANIE3160>3.0.CO;2-Z
Jason Lagona, James C. Fettinger, Lyle Isaacs, Cucurbit[n]uril analogues. Organic Letters. ,vol. 5, pp. 3745- 3747 ,(2003) , 10.1021/OL035468W