Selectively formylated and bridged calix[6]arene derivatives at the upper rim |
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Authors: | Jun-Min Liu Chuan-Feng Chen |
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Institution: | Beijing National Laboratory for Molecular Sciences, Research Center of Chemical Biology, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China |
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Abstract: | The strategy of bridging the anisole units at the upper rim of calix6]arene has been applied to strain the conformations of calix6]arene. Based on the selective formylation of the 1,3,5-tri-p-tert-butylcalix6]arene, several new calix6]arene derivatives with different 1,3-bridged chains or a 1,3,5-tripod bridge at the upper rim have been prepared with moderate yields. The 1H NMR spectra indicate that these calix6]arene derivatives adopt a cone conformation, which has also been confirmed by the theoretical calculation at AM1 level. X-ray crystal structure of 1,3,5-tripod bridged compound 5 discloses that the calix6]arene host stands in a cone conformation with approximate C3v symmetry, and that a methanol molecule is enclosed in its hydrophobic cavity and stabilized by multi hydrogen bonds. |
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Keywords: | Calix[6]arene Upper-rim-bridged 1 3 5-Tripod-bridged Supramolecular chemistry Inclusion compounds |
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