Novel self-assembling system based on resorcinarene and cationic surfactant

Phys Chem Chem Phys. 2011 Sep 21;13(35):15891-8. doi: 10.1039/c1cp20906j. Epub 2011 Aug 5.

Abstract

Mixed association of calix[4]resorcinarene with ethyl sulfonate groups on the lower rim and dimethylaminomethyl groups on the upper rim (CR) and cationic surfactant 4-aza-1-hexadecyl-azoniabicyclo[2.2.2]octane bromide (DABCO-16) is studied by methods of tensiometry, conductometry, potentiometry and NMR spectroscopy at fixed CR concentration and varied surfactant concentration. Beyond ca. 0.4 mM of DABCO-16, mixed aggregates enriched by CR are proved to be formed due to electrostatic forces, while beyond ca. 5 mM, aggregates enriched by surfactant occur due to the hydrophobic effect. Spectrophotometry monitoring of the solubilization of a hydrophobic dye, Orange OT, demonstrated that only the second type of mixed aggregate enriched by DABCO-16 is capable of binding the organic probe, while the mixed system where the surfactant is a minor component shows no binding capacity towards Orange OT. This finding can be used for the design of nanocontainers with controllable binding/release properties.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Calixarenes / chemistry*
  • Cations / chemistry
  • Conductometry
  • Magnetic Resonance Spectroscopy
  • Phenylalanine / analogs & derivatives*
  • Phenylalanine / chemistry
  • Piperazines / chemistry
  • Potentiometry
  • Solubility
  • Sulfonic Acids / chemistry
  • Surface-Active Agents / chemistry*

Substances

  • Cations
  • Piperazines
  • Sulfonic Acids
  • Surface-Active Agents
  • resorcinarene
  • Calixarenes
  • Phenylalanine
  • triethylenediamine