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Synthesis, Surface Activity, and Antimicrobial Efficacy of Diaryliodonium Salt‐Derived Amphiphiles
Author(s) -
Huang Mengen,
Xu Shujia,
Wu Xunshen,
Zhao Min,
Wang Limin
Publication year - 2018
Publication title -
journal of surfactants and detergents
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.349
H-Index - 48
eISSN - 1558-9293
pISSN - 1097-3958
DOI - 10.1002/jsde.12038
Subject(s) - chemistry , salt (chemistry) , antimicrobial , critical micelle concentration , nuclear chemistry , surface tension , organic chemistry , micelle , aqueous solution , physics , quantum mechanics
Two sets of 19 amphiphiles derived from diaryliodonium salt in the form of 4‐methylbenzenesulfonate salts and trifluoromethanesulfonate salts were synthesized in good yields through the oxidation of 17 different aryl iodides using oxone (potassium peroxymonosulfate) as the oxidation agent in Route I and meta‐chloroperoxybenzoic acid as the oxidation agent in Routes II and III, followed by Friedel–Crafts reaction with (2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy)benzene to obtain the target compounds ( 1 – 19 ). Their structures were characterized by 1 H nuclear magnetic resonance (NMR), 13 C NMR, and high‐resolution mass spectrometry studies. Their surface activities were evaluated on the basis of surface tension and critical micelle concentration measurements by the Wilhelmy plate method at 25 °C. With their good water solubility, diaryliodonium salts ( 1 – 19 ) have excellent short‐term bactericidal efficacy against Bacillus cereus in the concentration of 600 ppm at 20 °C. After compounding 1 or 18 with the broad‐spectrum but skin‐irritating antibacterial agent Kathon CG (methylchloroisothiazolinone in combination with methylisothiazolinone) in the ratio of 1:1 by mass, both formulations maintained lethality rate of >90% after 48 h.