Specific optical rotation is a versatile tool for the identification of critical micelle concentration and micellar growth of tartaric acid–based diastereomeric amphiphiles. Issue 12 (9th October 2017)

• Record Type: Journal Article
• Authors: Raghavan, Vijay; Polavarapu, Prasad L.
• Is Part Of: Chirality. Volume 29:Issue 12(2017)
• Page Start: 836
• Page End: 846
• Publication Date: 2017-10-09
• Subjects: aggregates -- critical micelle concentration -- diastereomers -- electronic circular dichroism -- enantiomers -- optical rotation -- surface tension -- surfactants -- vibrational circular dichroism; Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.22767
• Languages: English
• ISSNs: 0899-0042

Abstract

Abstract: Four novel tartaric acid–based diastereomeric chiral amphiphiles, two being enantiomers of the other two, have been synthesized and investigated using chiroptical spectroscopic methods, along with tensiometry and dynamic light scattering experiments. We found that an inflection point in specific optical rotation (SOR) values at ~0.32 mM corresponds to the critical micelle concentration (CMC). The increase in magnitude of SOR values beyond CMC corresponds to the growth of aggregates. For enantiomers, oppositely signed SOR values were observed, ruling out the possibility for the presence of aggregation size mediated artefacts. SOR values did not exhibit concentration dependence for a chiral tartaric acid based non‐aggregating analogue further establishing the absence of artefacts or anomalous interaction of tartaric acid based head group with solvent. Electronic circular dichroism spectra showed no significant changes in band positions or intensities with concentration. Due to the requirement for higher concentrations (~200 mM) needed to obtain vibrational circular dichroism spectra, these measurements are not found to be useful for studying concentration dependent properties of chiral amphiphiles. Abstract :