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<p>The guest encapsulation behavior and solid-state supramolecular assembly of four bromoethoxy-substituted pillar[5]arenes were investigated. These macrocycles selectively encapsulate 1,4-dibromobutane from equimolar mixtures of four α,ω-dibromoalkanes, forming 1:1 crystalline inclusion complexes. Single-crystal X-ray diffraction revealed that encapsulation is stabilized by C–H···π and C–H···O interactions within the macrocyclic cavity. The number and position of bromoethoxy groups significantly influence the supramolecular packing. While mono- and di-bromoethoxy-functionalized pillar[5]arenes exhibit only C–H···π and C–H···O interactions, the tetra- and hexa-bromoethoxy derivatives additionally display C–H···Br contacts, with the guest contributing to the assembly. Notably, the hexabromoethoxy-functionalized pillar[5]arene also exhibits Br···Br contacts, resulting in a distinct packing arrangement compared to the other systems.</p> Graphical Abstract <p></p>

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Host–Guest Recognition in the Crystalline State: Selective Inclusion of 1,4-Dibromobutane by Bromoethoxy-Functionalized Pillar[5]arenes

  • 期刊论文

  • 发表日期：

    2025年11月11日

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  • Mickey Vinodh,
  • Fatemeh H. Alipour,
  • Talal F. Al-Azemi

摘要

The guest encapsulation behavior and solid-state supramolecular assembly of four bromoethoxy-substituted pillar[5]arenes were investigated. These macrocycles selectively encapsulate 1,4-dibromobutane from equimolar mixtures of four α,ω-dibromoalkanes, forming 1:1 crystalline inclusion complexes. Single-crystal X-ray diffraction revealed that encapsulation is stabilized by C–H···π and C–H···O interactions within the macrocyclic cavity. The number and position of bromoethoxy groups significantly influence the supramolecular packing. While mono- and di-bromoethoxy-functionalized pillar[5]arenes exhibit only C–H···π and C–H···O interactions, the tetra- and hexa-bromoethoxy derivatives additionally display C–H···Br contacts, with the guest contributing to the assembly. Notably, the hexabromoethoxy-functionalized pillar[5]arene also exhibits Br···Br contacts, resulting in a distinct packing arrangement compared to the other systems.

Graphical Abstract