Hierarchical self-assembly of amphiphilic calix[6]arene wheels and viologen axles in water

Org Biomol Chem. 2013 Sep 21;11(35):5944-53. doi: 10.1039/c3ob40739j.

Abstract

We have designed and synthesized two amphiphilic calix[6]arene derivatives, CA8 and CA18, that combine the potential to act as wheel components for pseudorotaxane structures with the self-assembly features typical of surfactant molecules in aqueous solution. Their endo-cavity recognition and selfaggregation properties were compared with those of a non-amphiphilic analogue, C8. TEM, DLS, and fluorescence experiments show that in water the amphiphilic calixarenes form vesicle- and micelle-like aggregates. The size, nature and properties of such aggregates depend on the length of the alkyl chain anchored at the lower rim of the calix[6]arene skeleton, as well as on the inclusion of a molecular guest into the wheel. Specifically, the release of a fluorescent guest entrapped inside the CA8 vesicles is accelerated in the presence of dioctylviologen axles that can pierce the calixarene cavity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Calixarenes / chemical synthesis
  • Calixarenes / chemistry*
  • Micelles
  • Phenols / chemical synthesis
  • Phenols / chemistry*
  • Surface-Active Agents / chemical synthesis
  • Surface-Active Agents / chemistry*
  • Water / chemistry*

Substances

  • Micelles
  • Phenols
  • Surface-Active Agents
  • calix(6)arene
  • Water
  • Calixarenes