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<p>Examples of calix[4]arene ligands binding fluorescent organic dye molecules are very limited and usually focused on complexations at the calixarene upper rim, governed mostly by non-specific hydrophobic interactions. Herein, we report a spectrophotometric study of complexation of three selected dyes, namely, auramine O, rhodamine B, and fluorescein, by two disubstituted and one tetrasubstituted phenanthridine calix[4]arene derivative. The experimental investigation is accompanied by an exhaustive theoretical study of the structural features controlling the complexation, as well as optical properties of the formed complexes. It was shown that the studied ligands had high affinity towards the binding of the dyes and that π-π stacking interactions had an important role in the “sandwich” complex stabilization. The binding affinity of the tetrasubstituted ligand was particularly strong. Even more, upon binding the first dye molecule, this ligand proceeded to bind a sequential one, forming a stable complex with 2:1 stoichiometry with two sandwich complexes within a single calixarene host. Aside from the extent of the π -system and resulting strength of π-π interactions, additional factors like charge distribution and the presence of electron-withdrawing groups and sterically hindering groups, contributed to the overall stability of the complexes. The understanding of the structure-binding affinity relationship given by this study provides a solid foundation for further development of lower rim substituted calixarenes for molecular recognition.</p>

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Calix[4]arene phenanthridine derivatives as receptors for fluorescent dyes

  • 期刊论文

  • 发表日期：

    2026年6月3日

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  • Ita Hajdin,
  • Martina Perić Bakulić,
  • Bruna Delaš,
  • Marina Tranfić Bakić

摘要

Examples of calix[4]arene ligands binding fluorescent organic dye molecules are very limited and usually focused on complexations at the calixarene upper rim, governed mostly by non-specific hydrophobic interactions. Herein, we report a spectrophotometric study of complexation of three selected dyes, namely, auramine O, rhodamine B, and fluorescein, by two disubstituted and one tetrasubstituted phenanthridine calix[4]arene derivative. The experimental investigation is accompanied by an exhaustive theoretical study of the structural features controlling the complexation, as well as optical properties of the formed complexes. It was shown that the studied ligands had high affinity towards the binding of the dyes and that π-π stacking interactions had an important role in the “sandwich” complex stabilization. The binding affinity of the tetrasubstituted ligand was particularly strong. Even more, upon binding the first dye molecule, this ligand proceeded to bind a sequential one, forming a stable complex with 2:1 stoichiometry with two sandwich complexes within a single calixarene host. Aside from the extent of the π -system and resulting strength of π-π interactions, additional factors like charge distribution and the presence of electron-withdrawing groups and sterically hindering groups, contributed to the overall stability of the complexes. The understanding of the structure-binding affinity relationship given by this study provides a solid foundation for further development of lower rim substituted calixarenes for molecular recognition.