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Synthesis, Characterization, and Evaluation of Surface and Thermal Properties and Cytotoxicity of 2‐Hydroxy‐3‐Phenoxypropyl Imidazolium Bola‐Type Gemini Amphiphiles
Author(s) -
Aggarwal Rajni,
Singh Sukhprit,
Saini Vedangana,
Kaur Gurcharan
Publication year - 2019
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.12203
Subject(s) - chemistry , critical micelle concentration , amphiphile , aqueous solution , dynamic light scattering , micelle , gibbs isotherm , nuclear chemistry , organic chemistry , polymer chemistry , chemical engineering , nanoparticle , polymer , copolymer , engineering
A library of imidazolium‐based gemini cationic bola amphiphiles was synthesized using a regioselective ring‐opening reaction of glycidyl phenyl ether with imidazole under solvent‐free conditions. The corresponding hexafluorophosphate (PF 6 − ) and tetrafluoroborate (BF 4 − ) counterion‐containing amphiphiles were also synthesized and characterized using nuclear magnetic resonance (NMR) and mass spectroscopy. The micellar and interfacial parameters like the critical micelle concentration (CMC), surface pressure at the CMC (П cmc ), surface tension at CMC ( γ cmc ), counterion binding ( β ), maximum surface excess concentration ( Γ max ), minimum area per molecule ( A min ), standard free energy of micellization ( Δ G mic 0 ) and adsorption ( Δ G ads 0 ), and Kraft temperature were evaluated using surface tension and conductometry methods in aqueous solution as well as in buffer solution. Dynamic light scattering (DLS) was used to determine the size of the micelles formed in the aqueous solution. Cytotoxicity tests were carried out on the C6 glioma cancerous brain cell line using the MTT assay (3‐(4, 5‐dimethylthiazole‐2‐yl)‐2, 5‐diphenyltetrazolium bromide) to evaluate the IC 50 value of all the synthesized amphiphiles. Thermal stability of these amphiphiles was also evaluated using a thermal gravimetric analyzer (TGA). Economic way of synthesis, moderate thermal stability, a low value of CMC, and cytotoxicity of these amphiphiles will inspire new research in the field of nanobiotechnology and pharmaceutical industries.