Journal of Surfactants and Detergents

, Volume 14, Issue 4, pp 487–495 | Cite as

Surfactants Based on Bis-Galactobenzimidazolones: Synthesis, Self-Assembly and Ion Sensing Properties

  • L. Lakhrissi
  • N. Hassan
  • B. Lakhrissi
  • M. Massoui
  • E. M. Essassi
  • J. M. Ruso
  • C. Solans
  • C. Rodriguez- Abreu
Original Article

Abstract

A series of new non-ionic amphiphiles based on bis-galactobenzimidazolones have been synthesized by grafting alkyl bis-benzimidazolone units as hydrophobic tails on hydroxypropyloxygalacto-pyranose moieties as hydrophilic heads. Their surface and self-aggregation properties in water were evaluated. The compounds show very low critical micellar concentrations (CMCs) that decrease with increasing chain length; values for the minimal area per molecule at the interface (Amin) follow the same trend. The synthesized compounds also form hexagonal liquid crystals in water for a certain range of hydrophobic tail lengths. On the other hand, the new amphiphiles show characteristic UV–Vis absorption and fluorescence emission bands associated with the benzimidazolone moiety. The fluorescence emission is quenched with a certain degree of selectivity by cations, due to their strong affinity towards the benzimidazolone group, which shows ion complexation properties. Hence, the reported new amphiphiles are candidates as self-assembling chemosensors. The quenching efficiency and also ion sensing sensitivity is higher in the monomeric state as compared to the micellar state. The fluorescence emission intensity is higher for compounds with a shorter alkyl chain.

Keywords

Bis-benzimidazolones d-Galactose Surfactant synthesis Non-ionic surfactants Surface properties Fluorescence probe spectroscopy 

Supplementary material

11743_2011_1262_MOESM1_ESM.pdf (474 kb)
Supplementary material 1 (PDF 473 kb)

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Copyright information

© AOCS 2011

Authors and Affiliations

  • L. Lakhrissi
    • 1
    • 2
  • N. Hassan
    • 3
  • B. Lakhrissi
    • 1
  • M. Massoui
    • 2
  • E. M. Essassi
    • 2
  • J. M. Ruso
    • 3
  • C. Solans
    • 4
  • C. Rodriguez- Abreu
    • 4
    • 5
  1. 1.Laboratoire d’Agroressources et Génie des Procédés, Faculté des SciencesUniversité Ibn TofaïlKénitraMorocco
  2. 2.Laboratoire de Chimie Hétérocyclique, Faculté des SciencesUniversité Mohamed VRabatMorocco
  3. 3.Soft Matter and Molecular Biophysics Group, Department of Applied PhysicsUniversity of Santiago de CompostelaSantiago de CompostelaSpain
  4. 4.Institut de Química Avançada de Catalunya (IQAC)Consejo Superior de Investigaciones Científicas (CSIC)BarcelonaSpain
  5. 5.International Iberian Nanotechnology LaboratoryBragaPortugal

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