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<p>The contamination of urban groundwater by synthetic organic compounds represents a growing environmental concern; therefore, the development of supramolecular systems capable of selectively recognizing pollutants in aqueous environments is increasingly important, both for detection and remediation purposes. Herein, we report the synthesis of a water-soluble prism[6]arene extensively functionalized with sulfate groups at both rims. This host exhibits remarkable binding affinities toward organic dyes, specifically rhodamine B and methylene blue. The binding properties with these guests were investigated via UV–vis, fluorescence, NMR, DLS, DOSY, and ITC. Notably, in the presence of rhodamine B, the sulfated prism[6]arene forms both 1:1 endo-cavity and 1:2 capsular complexes, as evidenced by multi-technique characterization. Furthermore, in silico calculations suggest that two macrocycle units assemble into a water-bridged supramolecular capsule that encapsulates one molecule of rhodamine B. In contrast, methylene blue exclusively forms 1:1 endo-cavity complexes. These findings establish sulfated prism[6]arene as a promising water-soluble macrocycle paving the way for applications in environmental remediation.</p><p></p>

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Sulfated prism[6]arene as a water-soluble host for molecular recognition of dye pollutants in aqueous environments

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2026年6月17日

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  • Anna Palmieri,
  • Paolo Della Sala,
  • Rocco Del Regno,
  • Nicola Di Filippo,
  • Veronica Iuliano,
  • Carmen Talotta,
  • Margherita De Rosa,
  • Maria Carla Aragoni,
  • Claudia Caltagirone,
  • Giacomo Picci,
  • Marta Zaleskaya-Hernik,
  • Giuseppina D. G. Santonoceta,
  • Carmelo Sgarlata,
  • Carmine Gaeta

摘要

The contamination of urban groundwater by synthetic organic compounds represents a growing environmental concern; therefore, the development of supramolecular systems capable of selectively recognizing pollutants in aqueous environments is increasingly important, both for detection and remediation purposes. Herein, we report the synthesis of a water-soluble prism[6]arene extensively functionalized with sulfate groups at both rims. This host exhibits remarkable binding affinities toward organic dyes, specifically rhodamine B and methylene blue. The binding properties with these guests were investigated via UV–vis, fluorescence, NMR, DLS, DOSY, and ITC. Notably, in the presence of rhodamine B, the sulfated prism[6]arene forms both 1:1 endo-cavity and 1:2 capsular complexes, as evidenced by multi-technique characterization. Furthermore, in silico calculations suggest that two macrocycle units assemble into a water-bridged supramolecular capsule that encapsulates one molecule of rhodamine B. In contrast, methylene blue exclusively forms 1:1 endo-cavity complexes. These findings establish sulfated prism[6]arene as a promising water-soluble macrocycle paving the way for applications in environmental remediation.