Synthesis of a new zwitterionic surfactant containing an imidazolium ring. Evaluating the chameleon-like behavior of zwitterionic micelles

Synthesis of a new zwitterionic surfactant containing the imidazolium ring 3-(1-tetradecyl-3-imidazolio)propanesulfonate (ImS3-14) is described. The solubility of ImS3-14 is very low but increases on addition of a salt which helps to stabilize the micellized surfactant. Fluorescence quenching and el...

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Veröffentlicht in:Langmuir : the ACS journal of surfaces and colloids. - 1992. - 26(2010), 20 vom: 19. Okt., Seite 15754-60
1. Verfasser: Tondo, Daniel W (VerfasserIn)
Weitere Verfasser: Leopoldino, Elder C, Souza, Bruno S, Micke, Gustavo A, Costa, Ana C O, Fiedler, Haidi D, Bunton, Clifford A, Nome, Faruk
Format: Online-Aufsatz
Sprache:English
Veröffentlicht: 2010
Zugriff auf das übergeordnete Werk:Langmuir : the ACS journal of surfaces and colloids
Schlagworte:Journal Article
Beschreibung
Zusammenfassung:Synthesis of a new zwitterionic surfactant containing the imidazolium ring 3-(1-tetradecyl-3-imidazolio)propanesulfonate (ImS3-14) is described. The solubility of ImS3-14 is very low but increases on addition of a salt which helps to stabilize the micellized surfactant. Fluorescence quenching and electrophoretic evidence for ImS3-14 shows that the micellar aggregation number is only slightly sensitive to added salts, as is the critical micelle concentration, but NaClO(4) markedly increases zeta potentials of ImS3-14 in a similar way as in N-tetradecyl-N,N-dimethylammonio-1-propanesulfonate (SB3-14) micelles. The rate of specific hydrogen ion catalyzed hydrolysis of 2-(p-heptoxyphenyl)-1,3-dioxolane and equilibrium protonation of 1-hydroxy-2-naphthoate ion in zwitterionic micelles of ImS3-14 and SB3-14 are increased markedly by NaClO(4) which induces anionoid character and uptake of H(3)O(+), but NaCl is much less effective in this respect. Comparison of ImS3-14 with SB3-14 is based on experimental evidence, and computational calculations indicate similarities and differences in structures of both compounds
Beschreibung:Date Completed 21.01.2011
Date Revised 12.10.2010
published: Print
Citation Status PubMed-not-MEDLINE
ISSN:1520-5827
DOI:10.1021/la102391e