Acyclic congener of cucurbituril: synthesis and recognition properties |
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Authors: | Burnett Christopher A Witt Dariusz Fettinger James C Isaacs Lyle |
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Affiliation: | Department of Chemistry and Biochemistry, University of Maryland, College Park, College Park, Maryland 20742, USA. |
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Abstract: | The cucurbit[n]uril (CB[n]) family of macrocycles occupies a prominent role in molecular recognition and self-assembly studies despite the current inability to access specific cucurbit[n]uril homologues, derivatives, and analogues by straightforward tailor-made synthetic procedures. In this paper, we explore an approach that circumvents the challenges posed by the tailor-made synthesis of macrocyclic CB[n] by preparing 1, which functions as an acyclic CB[6] congener. The o-xylylene connections to the glycoluril rings preorganize 1 into the (a,a,a,a)-1 conformation required for binding and reduce its tendency to undergo self-association. We surveyed the binding properties of 1 toward 16 amines (K(a)
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