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Micellization of selenium-containing cationic surfactants with different headgroups in aqueous solution

  • Zhiqiang Chen
  • Xiaofei Ren
  • Shuang Guo
  • Xiaoyi Zhang
  • Rong Zhang
  • Mingrui Zhang
  • Dongyan Li
  • Qinglin Gu
  • Yongmin Zhang
Original Contribution
  • 69 Downloads

Abstract

Redox-responsive surfactant based on selenium atom has recently attracted considerable interests. Herein, we have designed and synthesized three selenium-containing cationic surfactants with different headgroups, including N-(benzylselanyl-undecyl)-N,N,N-trimethyl ammonium bromide (BSeTAB)/pyridinium bromide (BSePyB)/methylpyrrolidinium bromide (BSeMPB). Their micellization in dilute solution was investigated by surface tension and conductivity, and was related to redox-induced change in molecular structure. Both 1H NMR and ESI-MS spectra demonstrated that selenide in the reduced form is transformed into selenoxide after oxidation with H2O2, whatever the headgroup is. The formation of selenoxide not only increases the hydrophilicity of surfactant, resulting in a more negative \( \Delta {G}_{\mathrm{ads}}^o \), larger cmc, cmc/C20 ratio, and Gmin, compared to the reduced forms, but also provides a new polar headgroup, making it behave like bola-type structure and enhancing the hydrophilicity. The relatively smaller cmc, larger cmc/C20 ratio, and more negative \( \Delta {G}_m^o \) value all revealed that the pyridinium or pyrrolidinium polar headgroup is more favorable for the micelle formation than the trimethylammonium group. The thermodynamic parameters showed that the micellization is transformed from entropy-driven mode to enthalpy-driven mode with increasing temperature and the transition temperature at which \( \Delta {H}_m^o \) equals to \( -\mathrm{T}\Delta {S}_m^o \) is lowest for BSeMPB, and highest for BSePyB.

Keywords

Aggregation Micelles Micellization Surfactants Surface tension 

Notes

Funding information

This work was financially supported by the National Natural Science Foundation of China (grant No. 21503094, 21673103), the Natural Science Foundation (BK20150128) of Jiangsu Province, PR China, and Excellence project of teacher of Jiangnan University (JC2017134).

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

396_2018_4454_MOESM1_ESM.docx (451 kb)
ESM 1 (DOCX 450 kb)

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Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, School of Chemical and Materials EngineeringJiangnan UniversityWuxiPeople’s Republic of China

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