Synthesis of a novel type of hybrid fluorocarbon ionic surfactants containing polyoxyethlene chain

Li, Yan; Chen, Zhiqi; Tian, Juan; Zhou, Yuefei; Chen, Zuxing; Liu, Zhaojie

doi:10.1016/j.jfluchem.2005.03.015

Cited by 6 publications

(2 citation statements)

References 17 publications

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“…For the synthesis of C 12 E 23 N + SO 3 − F 8 , Brij 35 (0.005 mol), triethylamine (0.0125 mol), and perfluoro-1-octanesulfonyl fluoride (0.005 mol) were reacted in ether with vigorous stirring at 40 °C for 24 h. Ether was removed from the mixture by evaporation in a vacuum and C 12 E 23 N + SO 3 − F 8 was taken by 40:1 (v/v) ether:ethanol. After evaporation of 40:1 (v/v) ether:ethanol the product was purified by washing with first 1:1 (v/v) ether:hexane and then with hexane several times. , …”

Section: Methodsmentioning

confidence: 99%

A New Strategy To Form Multicompartment Micelles: Fluorocarbon−Hydrocarbon Ion-Pair Surfactant

Unsal

Aydoğan

2009

Langmuir

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The hydrophobic core of the multicompartment micelles consists of incompatible and clearly separated distinct subdomains which make them different from the classical micelles. Owing to these properties multicompartment micelles have a great potential to be used as solubilization agents and carriers for a wide variety of applications where it is important to prevent the uncontrolled interaction of the solubilizates before reaching the target and to convey them to the specified point simultaneously. Here we show that effective compartmentalization inside the micelle and high solubilization capacity for the two immiscible water-insoluble materials in cases of both simultaneous and separate solubilization can be achieved by newly designed ion-pair hybrid surfactant CH(3)(CH(2))(11)(OCH(2)CH(2))(23)N(+)(C(2)H(5))(3)SO(3)(-)(CF(2))(7)CF(3) (C(12)E(23)N(+)SO(3)(-)F(8)) through the agency of favorable molecular design. Molecular structure is tailored by the approach of using a balance of forces to obtain compartmentalization, which is without precedent. This new molecule also has the properties of quite low critical micelle concentration and an extensive surfactant concentration range for solubilization which are additional important advantageous features.

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Section: Methodsmentioning

confidence: 99%

A New Strategy To Form Multicompartment Micelles: Fluorocarbon−Hydrocarbon Ion-Pair Surfactant

Unsal

Aydoğan

2009

Langmuir

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“…13 The high reactivity of the perfluoroalkyl sulfonate group has been reported to lead to the problematic formation of ammonium sulfonate salts. 14,15 To see whether this unwanted incorporation of 19 F could be reduced, a precursor with a four-carbon perfluoroalkyl chain (3) was used. The outcome of this labelling reaction was, however, the same as for the reaction of compound 2.…”

Section: Introductionmentioning

confidence: 99%

Use of perfluoro groups in nucleophilic ¹⁸F‐fluorination

Blom¹,

Karimi²,

Långström³

2009

Labelled Comp Radiopharmac

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Substrates with leaving groups that contained perfluoro moieties were investigated in labelling chemistry in order to exploit their properties to improve reactivity and purification. [18 F](Fluoromethyl)benzene was used as the model target compound. Precursors containing perfluoroalkyl and perfluoroaryl sulfonate moieties were subjected to nucleophilic 18 F-fluorination, and the impact of perfluoro groups on the substitution reaction and product purification was investigated. [ 18 F]Fluoride interacted with perfluoroalkyl chains, precluding nucleophilic substitution. When perfluoroaryl groups were used, the substitution proceeded, and the separation of product was explored. The radiolabelled product was obtained in 32% analytical yield and the radiochemical purity was increased to approximately 77% using fluorous solid phase extraction purification.

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Fluorous Synthesis of ¹⁸F Radiotracers with the [¹⁸F]Fluoride Ion: Nucleophilic Fluorination as the Detagging Process

Béjot¹,

Fowler²,

Carroll³

et al. 2008

Angewandte Chemie

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Markieren leicht gemacht: Der Austausch einer hoch fluorierten Sulfonatmarkierung gegen [18F]‐Fluorid erwies sich als vorteilhaft für die Erzeugung 18F‐markierter prosthetischer Gruppen und bekannter Radiotracer (siehe Bild). Eine fluorige Festphasenextraktion (FSPE) trennte den Überschuss der hoch fluorierten Vorstufe vom markierten Material, sodass auf eine Destillation oder andere aufwändige Trennverfahren verzichtet werden kann.

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Synthesis of a novel type of hybrid fluorocarbon ionic surfactants containing polyoxyethlene chain

Cited by 6 publications

References 17 publications

A New Strategy To Form Multicompartment Micelles: Fluorocarbon−Hydrocarbon Ion-Pair Surfactant

A New Strategy To Form Multicompartment Micelles: Fluorocarbon−Hydrocarbon Ion-Pair Surfactant

Use of perfluoro groups in nucleophilic ¹⁸F‐fluorination

Fluorous Synthesis of ¹⁸F Radiotracers with the [¹⁸F]Fluoride Ion: Nucleophilic Fluorination as the Detagging Process

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Synthesis of a novel type of hybrid fluorocarbon ionic surfactants containing polyoxyethlene chain

Cited by 6 publications

References 17 publications

A New Strategy To Form Multicompartment Micelles: Fluorocarbon−Hydrocarbon Ion-Pair Surfactant

A New Strategy To Form Multicompartment Micelles: Fluorocarbon−Hydrocarbon Ion-Pair Surfactant

Use of perfluoro groups in nucleophilic 18F‐fluorination

Fluorous Synthesis of 18F Radiotracers with the [18F]Fluoride Ion: Nucleophilic Fluorination as the Detagging Process

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Use of perfluoro groups in nucleophilic ¹⁸F‐fluorination

Fluorous Synthesis of ¹⁸F Radiotracers with the [¹⁸F]Fluoride Ion: Nucleophilic Fluorination as the Detagging Process