Thermally cleavable surfactants based on furan-maleimide diels-alder adducts

James R. McElhanon, Thomas Zifer, Steven R. Kline, David R. Wheeler, Douglas A. Loy, Gregory M. Jamison, Timothy M. Long, Kamyar Rahimian, Blake A. Simmons

Research output: Contribution to journalArticlepeer-review

75 Scopus citations


Two new surfactant molecules are reported that contain thermally labile Diels-Alder adducts connecting the hydrophilic and hydrophobic sections of each molecule. The two surfactants possess identical hydrophobic dodecyl tail segments but have phenol and carboxylic acid hydrophilic headgroups, respectively. Deprotonation with potassium hydroxide affords the formation of water-soluble surfactants. Room temperature aqueous solutions of both surfactants exhibit classical surface-active agent behavior similar to common analagous alkylaryl surfactant molecules. Critical micelle concentrations have been determined for each surfactant through dynamic surface tension and dye solubilization techniques. Small-angle neutron scattering measurements of the aqueous surfactant solutions indicate the presence of spherical micelles with radii of 16.5 Å for the carboxylate and 18.8 Å for the phenolate. When these surfactants are exposed to elevated temperatures (>50°C), the retro Diels-Alder reaction occurs, yielding hydrophilic and hydrophobic fragments. Aqueous solutions of each surfactant subsequently exhibit a loss of all surface-active behavior and the micellar aggregates are no longer detectable.

Original languageEnglish (US)
Pages (from-to)3259-3266
Number of pages8
Issue number8
StatePublished - Apr 12 2005

ASJC Scopus subject areas

  • General Materials Science
  • Condensed Matter Physics
  • Surfaces and Interfaces
  • Spectroscopy
  • Electrochemistry


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