Enhanced Aggregation of Stimuli Responsive Surfactants by Esterolytic Reactions

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  • Asakawa Tsuyoshi
    School of Chemistry, College of Science and Engineering, Kanazawa University
  • Fujii Akina
    School of Chemistry, College of Science and Engineering, Kanazawa University
  • Yoneda Nodoka
    School of Chemistry, College of Science and Engineering, Kanazawa University
  • Ohta Akio
    School of Chemistry, College of Science and Engineering, Kanazawa University
  • Asakawa Hitoshi
    School of Chemistry, College of Science and Engineering, Kanazawa University

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<p>Thioester surfactants, [C12H25N(CH3)2(CH2)mSCOCH3] Br (C12mSAc, m = 4, 11, 12), yielded thiol surfactants via thiol-thioester exchange upon addition of dithiothreitol in aqueous solution. The thiolthioester exchange reaction was enhanced in a micellar system owing to the concentration effect. The enhanced aggregation upon deprotection of the thioacetate group was observed by dynamic light scattering measurements. The thiol surfactants yielded disulfide-linked gemini surfactants upon air oxidation and incubation with hydrogen peroxide. In contrast, the thiol surfactants yielded thioester double-tailed products by esterolytic reactions with p-nitrophenyl hexanoate. The introduction of an alkyl chain to the second side chain significantly decreased the critical micelle concentration and induced the micellar growth.</p>

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