Amphiphilic perfluoroalkylated sulfones and sulfonate betaines

Surface-active properties of nitrogen heterocyclic and dialkylamino derivates of hexadecylphosphocholine and cetyltrimethylammonium bromide

“…Cetyltrimethylammonium bromide (CTAB) is a typical representative of a monoQUAT. Its critical micellar concentration (cmc) value (8.5 Â 10 À4 mol dm À3 [23]) is higher than cmc values of other types of typical anionic (sodium hexadecylsulfate, 5.8 Â 10 À4 mol dm À3 at 40°C [24]), zwitterionic (2-(N-hexadecyl-N,N-dimethylammonium)-ethanoate, 2 Â 10 À5 mol dm À3 [25]), or nonionic (3,6,9,12,15,18-hexaoxatetratriacontanol, 1.7 Â 10 À6 mol dm À3 [26]) surfactants with the same alkyl chain lengths. CTAB forms very small micelles (5.4 nm in diameter) in water solution [27].…”

“…They are electrically neutral but the charges they carry in the zwitterionic head group affect their hydrophilicity [8][9][10]. The common zwitterionic surfactants are betaines [11], sulfobetaines [9,12], and phosphocholines [13,14]. They also can exist in the form of dimers, oligomers, or polymers.…”

Synthesis and the Structure to Property Relationship of Monoperfluoroalkyl Polyethylene Glycol

“…Monoprotected polyethylene glycol was epoxidized by the reaction of its monoprotected derivative 2 with epichlorohydrin [11,12]. The coupling reaction of the epoxide 3 and 2-F-alkylethanethiol [13][14][15][16][17][18][19][20] furnished the adduct 4, which was easily deprotected [9] into surfactant 5 (Scheme 1).…”

Zwitterionic fluorinated detergents: From design to membrane protein applications

“…The reaction of dimethylamine 4 with propane-1,3sultone yielded the sulfobetaine derivative F 6 H 3 SB (6) as a white precipitate in 77% yield. Of note, F 6 H 3 SB had already been synthesized following another synthetic route in two steps starting from 3-(perfluorohexyl)propyl iodide [23]. Despite being 3 steps longer, our strategy uses a fluorinated starting material that is significantly cheaper, which makes the scale-up of the synthesis more conceivable.…”