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<p>A thiacalix[4]arene with four azido groups on the upper rim and free hydroxy groups on the lower rim was synthesized for the first time by the diazotization reaction. A procedure for the synthesis of diazido derivatives of calix[4]arenes and thiacalix[4]arenes with free phenolic hydroxy groups <i>via</i> benzoyl protection of OH groups was developed and optimized. A similar technique was used to synthesize a monoazido derivative of calix[4]arene, the parent compound for the biscalix[4]arenes with ethylene glycol and dihydroxyphenylene linkers obtained by the azide-alkyne cycloaddition reaction. It was demonstrated that these biscalix[4]arenes can bind the cationic dye rhodamine 6G, which is not observed for the starting de-<i>tert</i>-butylated calix[4]arene. It was established that the biscalix[4]arene—rhodamine 6G system can be used for the recognition of cationic surfactants and that the more lipophilic the surfactant, the more pronounced the system’s response.</p>

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Mono-, di-, and tetraazido derivatives of (thia)calix[4]arenes with free phenolic hydroxy groups

  • 期刊论文

  • 发表日期：

    2025年4月1日

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  • E. G. Makarov,
  • Z. E. Iskhakova,
  • V. A. Burilov,
  • S. E. Solovieva,
  • I. S. Antipin

摘要

A thiacalix[4]arene with four azido groups on the upper rim and free hydroxy groups on the lower rim was synthesized for the first time by the diazotization reaction. A procedure for the synthesis of diazido derivatives of calix[4]arenes and thiacalix[4]arenes with free phenolic hydroxy groups via benzoyl protection of OH groups was developed and optimized. A similar technique was used to synthesize a monoazido derivative of calix[4]arene, the parent compound for the biscalix[4]arenes with ethylene glycol and dihydroxyphenylene linkers obtained by the azide-alkyne cycloaddition reaction. It was demonstrated that these biscalix[4]arenes can bind the cationic dye rhodamine 6G, which is not observed for the starting de-tert-butylated calix[4]arene. It was established that the biscalix[4]arene—rhodamine 6G system can be used for the recognition of cationic surfactants and that the more lipophilic the surfactant, the more pronounced the system’s response.