Synthesis and properties of mono-O-[(N-(aminoalkyl)aminocarbonyl)-methoxy]thiacalix[4]arenes and novel mono-O-bridged bisthiacalix[4]arene |
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Authors: | Meriem Lamouchi Erwann JeanneauJérémy Coulm Arnaud BrioudeCédric Desroches |
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Institution: | Laboratoire des multimatériaux et interfaces (UMR 5615), université Claude-Bernard–Lyon-1, campus de La Doua, 69622 Villeurbanne cedex, France |
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Abstract: | A simple method for thiacalix4]arene O-monoamide preparation with high yields using 5,11,17,23-tetra-tert-butyl-28-(ethoxycarbonyl)methoxy-2,8,14,20-tetrathiacalix4]arene reaction with diaminoalkanes is reported. The solid state cyclization reaction of the acylethylenediamines function of 5,11,17,23-tetra-tert-butyl-28-O-(N-(2-aminoethyl)aminocarbonyl)-methoxy]thiacalix4]arene leading to the formation of the 5,11,17,23-tetra-tert-butyl-28-2-methoxy-imdazoline]thiacalix4]arene compound is described for the first time for the calixarene macrocycle family. Finally, preliminary results show that O-mono-amide-thiacalixarene derivatives are promising candidates for the production of self-assembled materials and efficient precursors for the synthesis of bisthiacalix4] arenes. |
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Keywords: | Thiacalix[4]arene Synthesis Monosubstitution Solid state structure Self-assembling |
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