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Keywords:

  • Supramolecular chemistry;
  • Host–guest systems;
  • Molecular recognition;
  • Binding mechanisms;
  • Macrocycles

Abstract

To clarify the binding mechanisms and driving forces for the unique ability of pillar[5]arenes to recognize neutral molecules, the complexation of a series of nitrogen heterocycle substituted 1,4-butylene guests with pillar[5]arenes was studied. Guests molecules that have similar structures exhibit remarkably different association constants, and multiple weak C–H···N interactions between the alkyl groups of the pillar[5]arenes and the outer nitrogen atoms of the heterocycles of the guests are the dominant driving forces for complexation.