Anion receptors based on ureido-substituted thiacalix[4]arenes and calix[4]arenes |
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Authors: | Jan Kroupa,Michaela Pojarová ,Pavel Lhotá k |
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Affiliation: | a Department of Organic Chemistry, Institute of Chemical Technology, Technická 5, 16628 Prague 6, Czech Republic b Department of Solid State Chemistry, Institute of Chemical Technology, Technická 5, 16628 Prague 6, Czech Republic c Department of Analytical Chemistry, Institute of Chemical Technology, Technická 5, 16628 Prague 6, Czech Republic |
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Abstract: | The regioselective nitration of 25,27-dipropoxythiacalix[4]arene was carried out as a key step in the synthesis of thiacalix[4]arene derivative bearing two arylureido functions on the upper rim. The preorganisation of ureido units using the thiacalix[4]arene/calix[4]arene moieties as a molecular scaffold gave novel anion receptors. These compounds, albeit based on hydrogen bonding interactions, show good complexation ability even in highly HB-competitive solvent, such as DMSO. Direct comparison of otherwise identical structures 6a and 7a revealed remarkable dominance of the thiacalix[4]arene derivative over its classical analogue in anion binding. |
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Keywords: | Thiacalixarene Self-Assembly X-ray crystallography |
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