Glycine-based polymeric surfactants with varied polar head group: I. Synthesis, characterization, and application in micellar electrokinetic chromatography

Abstract

The monomers and polymers of four anionic amide type sodium undecenoxy carbonyl glycinate (SUCG) surfactants and four anionic carbamate type sodium undecenoyl glycinate (SUG) surfactants with 1-, 2-, 3-, and 4-glycine unit as head group were synthesized and characterized. The CMC and aggregation number (A) for all eight surfactants were determined using fluorescence spectroscopy. In addition, the CMC values of these surfactants were also projected by surface tension and CE. The CMC of the monomers decreases with increases in the size of glycine head groups and correlates well when the fluorescence method was compared to CE. The A number increases and partial specific volume (V) decreases with increase in size of the head group of both monomers and polymers. However, A and V are always lower for the polymers than the corresponding monomers. The electrophoretic and chromatographic parameters of micelle polymers of SUG and SUCG were also examined. The coefficient of EOF increases with the increase in size of the head group but the electrophoretic mobility decreases which results in a decrease in the elution range. The retention data suggest that the selectivity differences among the mono-, di-, and tripeptide derivatives of poly-SUCG surfactants are relatively higher compared to the derivatives of poly-SUG series.

Glycine-based polymeric surfactants with varied polar head group: II. Chemical selectivity in micellar electrokinetic chromatography using linear solvation energy relationships

“…C poly-SUG1 ). This trend differs with the partial specific volume results reported in Part I [31]. For example, for poly-SUG series of surfactants the chromatographic phase ratio (b) calculated from the proposed equation (Table 3, column 2).…”

“…methoxyphenethylamines (4-methoxyphenethylamines, 3-methoxyphenethylamines, 2-methoxy-phenethylamines) were obtained from Aldrich (Milwaukee, WI, USA). Other chemicals are essentially the same as in Part I [31].…”

Simultaneous chiral separation and determination of ephedrine alkaloids by MEKC‐ESI‐MS using polymeric surfactant I: Method development

“…In the past years, several types of polymeric surfactants (also known as micelle polymers or molecular micelles) have been synthesized and widely applied to enantioseparations in MEKC-UV [24][25][26][27][28]. For analysis of chiral compounds, the feasibility of direct coupling of MEKC to MS using polymeric surfactant was reported by our research group [29][30][31].…”

Recent progress in the use of ionic polymers as pseudostationary phases for EKC

“…1B) and undecenoyl glycinate (SUG n , Fig. 1C) surfactants and polymers with one, two, three, or four glycine units as the head group were reported [28,29]. The CMC of the surfactants were observed to decrease by approximately a factor of two with the addition of each glycine unit, while the aggregation numbers increased.…”