Iso-branched semifluorinated alkanes in Langmuir monolayers

Broniatowski, Marcin; Dynarowicz-Łątka, Patrycja

doi:10.1016/j.jcis.2006.02.053

Cited by 15 publications

(16 citation statements)

References 40 publications

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“…[7][8][9][10] So far, the majority of studies have been done on SFA molecules without any structural modifications. There are some papers regarding SFAs containing halogen atoms, such as Br and I, introduced in the terminal position of the H-chain, 11 or discussing the influence of the iso branching of the F-chain on the physical properties of these molecules; 12 however, such reports are not numerous. On the other hand, semifluorinated chains are often applied as components of classical surfactants terminated with the -OH, -COOH or other polar headgroups.…”

Section: Introductionmentioning

confidence: 99%

Partially Fluorinated Thioethers at the Water/Air Interface. Langmuir Monolayer Characterization and X-ray Scattering Studies

et al. 2010

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A series of partially fluorinated aliphatic thioethers of the following formula: CF(3)-(CF(2))(7)-(CH(2))(10)-S-C(n)H(2n+1), where n = 1, 2, 4, 8, 12, and 18, were synthesized and spread from chloroform solution onto the water/air interface in a Langmuir trough. Upon compression of the film, the surface pressure-mean molecular area isotherms were recorded. It turned out that all the investigated compounds are capable of stable Langmuir monolayers formation. The electrical properties of the studied monolayers have been investigated by monitoring the change in the surface potential (ΔV) upon film compression. The performed experiments proved that regardless of the length of the C(n)H(2n+1) chain, the orientation of the film molecules is very similar. The investigated monolayers have been visualized applying Brewster angle microscopy. The monolayers of the shorter homologues turned out to be homogeneous until their collapse, whereas for longer homologues, the formation of multilayer aggregates was observed. The methods of grazing incidence X-ray diffraction (GIXD) and X-ray reflectivity (XR) have also been applied for the characterization of the organization of thioether molecules in their monolayers. The GIXD experiments proved that the films of the studied thioethers possess a periodical in-plane structure. They are collectively tilted toward the next neighbor (NN tilt), and their packing within the monolayer (xy) plane can be described by the 2-dimentional rectangular centered lattice. Interpretation of the XR results indicate that only the partially fluorinated chain of the thioether molecule is periodically organized at the water/air interface, whereas the hydrocarbon chain is disordered and has a liquid character.

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Section: Introductionmentioning

confidence: 99%

Partially Fluorinated Thioethers at the Water/Air Interface. Langmuir Monolayer Characterization and X-ray Scattering Studies

et al. 2010

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“…Fluorinated surfactants take on hydrophobicity and lipophobicity at the same time and are also being expected in an industrial field. Partially fluorinated surfactants and alkanes, which have both the properties of hydrocarbons and fluorocarbons, have recently been investigated for the purpose of reducing their residual property to the human body and the environment [6][7][8][9][10][11][12][13]. However, the residual effect of perfluorinated surfactants on the human body is still unknown, although they have the possibility for use and application as blood substitutes [14] and lung surfactants [15,16].…”

Section: Introductionmentioning

confidence: 99%

“…The monolayers at the air-water interface have intensely been adopted as experimental paradigms of biomembranes for elucidating the interfacial properties and mechanisms of surfactants [7,[20][21][22]. The monolayer technique has an advantage in simplifying physicochemical behavior compared with that employed for three-dimensional (3D) aggregates such as micelles, vesicles, and emulsions.…”

Section: Introductionmentioning

confidence: 99%

Miscibility behavior of two-component monolayers at the air–water interface: Perfluorocarboxylic acids and DMPE

Yokoyama

Nakahara

Nakagawa

et al. 2009

Journal of Colloid and Interface Science

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“…However, the cross sectional area of an all-trans perfluorocarbon chain in a crystal phase is known to be 28 Å 2 . 33 Therefore, the small area of Nohead FC6-HC2 is likely invalid and probably arises due to some small solubility allowing some molecules of the spread monolayer to dissolve in water. Nohead FC6-HC4 gave an Amin smaller than that of the non-fluorinated Nohead HC6-HC4, but larger than the cross sectional area of an all-trans perfluorocarbon chain.…”

Section: Adsorption Of Nohead Fc6-hc4 At the Air-water Interfacementioning

confidence: 99%

New Class of Amphiphiles Designed for Use in Water-in-Supercritical CO₂ Microemulsions

et al. 2016

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Water-in-supercritical CO microemulsions formed using the hybrid F-H surfactant sodium 1-oxo-1-[4-(perfluorohexyl)phenyl]hexane-2-sulfonate, FC6-HC4, have recently been shown to have the highest water-solubilizing power ever reported. FC6-HC4 demonstrated the ability to outperform not only other surfactants but also other FCm-HCn analogues containing different fluorocarbon and hydrocarbon chain lengths (Sagisaka, M. et al. Langmuir 2015, 31, 7479-7487). With the aim of clarifying the key structural features of this surfactant, this study examined the phase behavior and water/supercritical CO aggregate formation of 1-oxo-1-[4-(perfluorohexyl)phenyl]hexane (Nohead FC6-HC4), which is an FC6-HC4 analogue but now, interestingly, without the sulfonate headgroup. Surprisingly, Nohead FC6-HC4, which would not normally be identified as a classic surfactant, yielded transparent single-phase W/CO microemulsions with polar cores able to solubilize a water-soluble dye, even at pressures and temperatures so low as to approach the critical point of CO (e.g., ∼100 bar at 35 °C). High-pressure small-angle scattering (SANS) measurements revealed the transparent phases to consist of ellipsoidal nanodroplets of water. The morphology of these droplets was shown to be dependent on the pressure, Nohead FC6-HC4 concentration, and water-to-surfactant molar ratio. Despite having almost the same structure as Nohead FC6-HC4, analogues containing both shorter and longer hydrocarbons were unable to form W/CO microemulsion droplets. This shows the importance of the role of the hydrocarbon chain in the stabilization of W/CO microemulsions. A detailed examination of the mechanism of Nohead FC6-HC4 adsorption onto the water surface suggests that the hexanoyl group protrudes into the aqueous core, allowing for association between the carbonyl group and water.

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Iso-branched semifluorinated alkanes in Langmuir monolayers

Cited by 15 publications

References 40 publications

Partially Fluorinated Thioethers at the Water/Air Interface. Langmuir Monolayer Characterization and X-ray Scattering Studies

Partially Fluorinated Thioethers at the Water/Air Interface. Langmuir Monolayer Characterization and X-ray Scattering Studies

Miscibility behavior of two-component monolayers at the air–water interface: Perfluorocarboxylic acids and DMPE

New Class of Amphiphiles Designed for Use in Water-in-Supercritical CO₂ Microemulsions

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Iso-branched semifluorinated alkanes in Langmuir monolayers

Cited by 15 publications

References 40 publications

Partially Fluorinated Thioethers at the Water/Air Interface. Langmuir Monolayer Characterization and X-ray Scattering Studies

Partially Fluorinated Thioethers at the Water/Air Interface. Langmuir Monolayer Characterization and X-ray Scattering Studies

Miscibility behavior of two-component monolayers at the air–water interface: Perfluorocarboxylic acids and DMPE

New Class of Amphiphiles Designed for Use in Water-in-Supercritical CO2 Microemulsions

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About

New Class of Amphiphiles Designed for Use in Water-in-Supercritical CO₂ Microemulsions