Perfluoroalkylated amphiphiles with a morpholinophosphate or a dimorpholinophosphate polar head group

Sadtler, Véronique; Jeanneaux, F.; Krafft, Marie Pierre; Rábai, József; Riess, Jean G.

doi:10.1039/a708757h

Cited by 37 publications

(20 citation statements)

References 10 publications

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“…(Perfluorooctyl)pentanol (F8C5OH) and (perfluorooctyl)pentylphosphocholine (F8C5PC) were synthesized as reported previously [43]. Tetradecanoic acid (Myristic acid, MA, 99-100%) was purchased from Sigma (St. Louis, MO) and was used without further purification.…”

Section: Methodsmentioning

confidence: 99%

Langmuir monolayer miscibility of single-chain partially fluorinated amphiphiles with tetradecanoic acid

Nakahara¹,

Tsuji²,

Sato³

et al. 2009

Journal of Colloid and Interface Science

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Section: Methodsmentioning

confidence: 99%

Langmuir monolayer miscibility of single-chain partially fluorinated amphiphiles with tetradecanoic acid

Nakahara¹,

Tsuji²,

Sato³

et al. 2009

Journal of Colloid and Interface Science

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“…[21,22] Methods: The surface tensions (g s ) of aqueous solutions of the FnCmDMPs were measured with an automatic Lauda tensiometer (Lecomte du Noüy method; platinum ring). Deionized water (g s 72 mN m À1 ) came from an Elgastat purification system.…”

Section: Methodsmentioning

confidence: 99%

Micellization and Adsorption of Fluorinated Amphiphiles: Questioning the 1 CF2≈1.5 CH2 Rule

Sadtler¹,

Giulieri²,

Krafft³

et al. 1998

Chem. Eur. J.

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The surface activity of a series of partially fluorinated amphiphiles with a dimorpholinophosphate polar head, a perfluoroalkyl terminal and a hydrocarbon spacer, C n F 2n1 (CH 2 ) m OP-(O)[N(CH 2 CH 2 ) 2 O] 2 (FnCmDMP, m 1 ± 11, n 4 ± 10), was investigated, and the contributions of the CF 2 and CH 2 groups to the energies of adsorption and micellization of the amphiphiles were determined. In the literature, such data are only available for amphiphiles with either totally fluorinated or totally hydrogenated hydrophobes. We determined the impact of the fluorocarbon segment on the contribution of the hydrocarbon spacer to the adsorption and micellization processes. DG mic and DG ads were evaluated as À 4.2 AE 0.5 and À 4.1 AE 0.6 kJ mol À1 per CF 2 group, consistent with results reported on totally fluorinated surfactants (À 3.3 to À 5.2 kJ mol À1 ). In contrast, the values for DG mic and DG ads per CH 2 group (À 1.0 AE 0.4 and À 1.0 AE 0.6 kJ mol À1 , respectively) were substantially lower than those measured for hydrocarbon analogues of the FnCmDMPs (À 2.4 AE 0.4 and À 2.5 AE 0.5 kJ mol À1 ), which fall in the range observed for standard hydrocarbon amphiphiles (À 2.4 to À 3.05 kJ mol À1 ). These results show that a hydrocarbon chain grafted to a fluori-nated chain does not fully participate in the micellization and adsorption processes, and behaves as if it were shorter by a factor of about three. Thus it is primarily the length of the fluorinated chain that controls micellization and adsorption of such surfactants; the spacer plays only a minor role, and great caution must be exercised when applying the 1 CF 2 % 1.5 CH 2 rule. It is proposed that the hydrocarbon spacer adopts a folded conformation in order to better occupy the void volume which results from the difference in crosssections between fluorocarbon and hydrocarbon chains (ca. 30 vs. 20 2 , respectively).

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“…Fluorosurfactants (Perfluoropolyethers -PFPE -with hydrophilic head groups) are used as emulsifiers for supercritical CO 2 124 and are perfectly suited to stabilize water in fluorinated oil emulsions. Although the carboxylic terminated PFPE has questionnable biocompatibility properties 125 , many other fluorinated surfactants have been reported to show very interesting biocompatibility properties 126 . For example some fluorinated surfactants with short fluorinated tails are used as therapeutic agents in lung deficiencies cases or for carrier of drugs through the pulmonary route 127,128 .…”

Section: Biocompatible Surfactantsmentioning

confidence: 99%

Surfactants in droplet-based microfluidics

2012

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Surfactants are an essential part of the droplet-based microfluidic technology. They are involved in the stabilization of droplet interfaces, in the biocompatibility of the system and in the process of molecular exchange between droplets. The recent progress in the applications of droplet-based microfluidics has been made possible by the development of new molecules and their characterizations. In this review, the role of the surfactant in droplet-based microfluidics is discussed with an emphasis on the new molecules developed specifically to overcome the limitations of 'standard' surfactants. Emulsion properties and interfacial rheology of surfactant-laden layers strongly determine the overall capabilities of the technology. Dynamic properties of droplets, interfaces and emulsions are therefore very important to be characterized, understood and controlled. In this respect, microfluidic systems themselves appear to be very powerful tools for the study of surfactant dynamics at the time- and length-scale relevant to the corresponding microfluidic applications. More generally, microfluidic systems are becoming a new type of experimental platform for the study of the dynamics of interfaces in complex systems.

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Perfluoroalkylated amphiphiles with a morpholinophosphate or a dimorpholinophosphate polar head group

Cited by 37 publications

References 10 publications

Langmuir monolayer miscibility of single-chain partially fluorinated amphiphiles with tetradecanoic acid

Langmuir monolayer miscibility of single-chain partially fluorinated amphiphiles with tetradecanoic acid

Micellization and Adsorption of Fluorinated Amphiphiles: Questioning the 1 CF2≈1.5 CH2 Rule

Surfactants in droplet-based microfluidics

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