Simultaneously Bound Guests and Chiral Recognition: A Chiral Self-Assembled Supramolecular Host Encapsulates Hydrophobic Guests

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Driven by the hydrophobic effect, a water-soluble, chiral, self-assembled supramolecular host is able to encapsulate hydrophobic organic guests in aqueous solution. Small aromatics can be encapsulated in the supramolecular assembly, and the simultaneous encapsulation of multiple guests is observed in many cases. The molecular host assembly is able to recognize different substitutional isomers of disubstituted benzenes with ortho substitution leading to the encapsulation of two guests, but meta or para substitution leading to the encapsulation of only one guest. The scope of hydrophobic guest encapsulation is further explored with chiral natural product guests. Upon encapsulation of chiral guests into the ... continued below

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Hastings, Courtney J.; Pluth, Michael D.; Biros, Shannon M.; Bergman, Robert G. & Raymond, Kenneth N. March 6, 2008.

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Driven by the hydrophobic effect, a water-soluble, chiral, self-assembled supramolecular host is able to encapsulate hydrophobic organic guests in aqueous solution. Small aromatics can be encapsulated in the supramolecular assembly, and the simultaneous encapsulation of multiple guests is observed in many cases. The molecular host assembly is able to recognize different substitutional isomers of disubstituted benzenes with ortho substitution leading to the encapsulation of two guests, but meta or para substitution leading to the encapsulation of only one guest. The scope of hydrophobic guest encapsulation is further explored with chiral natural product guests. Upon encapsulation of chiral guests into the racemic host, diastereomeric host-guest complexes are formed with observed diastereoselectivities of up to 78:22 in the case of fenchone.

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  • Journal Name: Tetrahedron

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  • Report No.: LBNL-1174E
  • Grant Number: DE-AC02-05CH11231
  • DOI: 10.1016/j.tet.2008.05.131 | External Link
  • Office of Scientific & Technical Information Report Number: 941712
  • Archival Resource Key: ark:/67531/metadc897280

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  • March 6, 2008

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  • Sept. 27, 2016, 1:39 a.m.

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  • Oct. 3, 2016, 2:22 p.m.

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Hastings, Courtney J.; Pluth, Michael D.; Biros, Shannon M.; Bergman, Robert G. & Raymond, Kenneth N. Simultaneously Bound Guests and Chiral Recognition: A Chiral Self-Assembled Supramolecular Host Encapsulates Hydrophobic Guests, article, March 6, 2008; Berkeley, California. (digital.library.unt.edu/ark:/67531/metadc897280/: accessed December 13, 2018), University of North Texas Libraries, Digital Library, digital.library.unt.edu; crediting UNT Libraries Government Documents Department.