134052-01-0Relevant academic research and scientific papers
Copper-catalyzed addition of perfluoroalkyl iodides to unsaturated alcohols and transformation of the addition products
Kotora, M.,Hajek, M.,Ameduri, B.,Boutevin, B.
, p. 49 - 56 (1994)
Iodoperfluoroalkyl alcohols RFCH2CHI(CR2)nOH (RF = C6F13; R = H, CH3; n = 1-3, 9) have been readily prepared in high yield by the addition of perfluoroalkyl iodides RFI to allylic and other unsaturated alcohols at 120 deg C in the presence of a catalytic amount (10percent mol) of metallic copper powder.The dibenzoyl peroxide-induced reaction gave lower yields of the addition products in most cases.The chemical changes of iodoperfluoroalkylated alcohols to epoxides and alcohols are described.A discussion of the by-products obtained and of the reaction mechanism is provided.
Synthesis and biocompatibility evaluation of partially fluorinated pyridinium bromides
Vyas, Sandhya M.,Turanek, Jaroslav,Knoetigova, Pavlina,Kasna, Andrea,Kvardova, Veronika,Koganti, Venkat,Rankin, Stephen E.,Knutson, Barbara L.,Lehmler, Hans-Joachim
, p. 944 - 951 (2006)
Although cationic surfactants are of general interest for a variety of consumer and biomedical applications, only a limited number of partially fluorinated, single-tailed, cationic surfactants have been synthesized. To study the potential usefulness of fluorinated cationic surfactants for these applications we synthesized a series of partially fluorinated pyridinium bromide surfactants. Three 10-perfluoroalkyldecyl pyridinium surfactants were synthesized by coupling a perfluoroalkyl iodide with 9-decene-1-yl acetate using an AIBN mediated radical reaction. The resulting 9-iodo-10-perfluoroalkyldec-1- yl acetates were deiodinated using HI-Zn-EtOH and hydrolyzed using KOH-EtOH to yield the corresponding 10-perfluoroalkyldecanol. The partially fluorinated alcohol was converted into the bromide using Br2-PPh3. Alkylation of excess pyridine with the bromides gave the desired 10-perfluoroalkyldecyl pyridinium bromides in good yields. Three 10-perfluoroalkylundecyl surfactants were synthesized using a similar approach with 10-undecenoic acid methyl ester as starting material. Based on an initial in vitro toxicity assessment, the toxicity of the partially fluorinated pyridinium surfactants was slightly lower or comparable to benzalkonium chloride, a typically cationic surfactant (with IC50s of tested compounds ranging from 5 to 15 μM). An increase in the length and/or the degree of fluorination of the hydrophobic tail correlated with a mild decrease of cytotoxicity and haemolytic activity. Partially fluorinated pyridinium surfactants may, therefore, be useful for biomedical applications such as components for novel gene and drug delivery systems. the Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2006.
Phase transfer synthesis of symmetrical di-terminally perfluorinated alkyl trithiocarbonates
Naud,Calas,Blancou,Commeyras
, p. 29 - 38 (2000)
Symmetrical di-terminally perfluorinated alkyl trithiocarbonates having the formula [F(CF2)n(CH2)mS]2CS (n = 4,6,8 m = 2 and n = 6,8 m = 11) were prepared in good yield under phase-transfer catalytic conditions starting from perfluoroalkyl alkyl iodides F(CF2)n(CH2)mI.
Lamellar Liquid Crystals of In-Plane Lying Rod-Like Mesogens with Designer Side-Chains: The Case of Sliding versus Locked Layers
Prehm, Marko,Enders, Claudia,Mang, Xiaobin,Zeng, Xiangbing,Liu, Feng,Ungar, Goran,Baumeister, Ute,Tschierske, Carsten
supporting information, p. 16072 - 16084 (2018/10/15)
The dimensionality of self-assembled nanostructures plays an essential role for their properties and applications. Herein, an understanding of the transition from weakly to strongly coupled layers in soft matter systems is provided involving in-plane organized π-conjugated rods. For this purpose, bolaamphiphilic triblock molecules consisting of a rigid biphenyl core, polar glycerol groups at the ends, and a branched (swallow-tail) or linear alkyl or semiperfluoroalkyl chain in lateral position have been synthesized and investigated. Besides weakly coupled lamellar isotropic (LamIso), lamellar nematic (LamN) and sliding lamellar smectic phases (LamSm), a sequence of three distinct types of strongly coupled (correlated) lamellar smectic phases with either centered (c2mm) or non-centered rectangular (p2mm) lattice and an intermediate oblique lattices (p2) were observed depending on chain length, chain branching and degree of chain fluorination. This new sequence is explained by the strengthening of the layer coupling and the competition between energetic packing constraints and the entropic contribution of either longitudinal or tangential fluctuations. This example of directed side chain engineering of small generic model compounds provides general clues for morphological design of two-dimensional and three-dimensionally coupled lamellar systems involving larger π-conjugated molecular rods and molecular or supramolecular polymers, being of actual interest in organic electronics and nanotechnology.
The fluorine-containing phosphoric acid ester compound and its salt surface-treating agent
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Paragraph 0063; 0064, (2017/05/18)
PROBLEM TO BE SOLVED: To provide novel fluorine-containing phosphoric ester compounds or salts thereof and surface treatment agents, which have sufficiently good surface characteristics such as releasability, water repellency, oil repellency, and low surface tension.SOLUTION: The invention provides fluorine-containing phosphoric ester compounds represented by the specified general formula (1) or salts thereof, and surface treatment agents containing the fluorine-containing phosphoric ester compounds or salts thereof. [Rf are each independently a perfluoroalkyl group having six or less carbon atoms; and n are each independently an integer between 4 and 12.
Sulphonic function fluorine compounds and their use
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Page/Page column 8-9, (2010/11/17)
The present invention relates to compounds containing a fluoro hydrocarbon terminal and a sulphonic function terminal obtained by a series of chaining reactions of a perfluorocarbon segment with elevated hydrophobic and oleophobic powers with an aliphatic segment containing heteroatoms (O, N, S), in turn terminated by a hydrophilic sulphonic group in the form of a free acid or salt with an alkaline or ammonium ion. Such compounds also have excellent amphipatic properties in highly saline aqueous environments. The present invention relates further to the use of the compounds described.
Synthesis of terminally perfluorinated long-chain alkanethiols, sulfides and disulfides from the corresponding halides
Naud,Calas,Blancou,Commeyras
, p. 173 - 183 (2007/10/03)
Semifluorinated n-alkanethiols, symmetrical sulfides and disulfides bearing the chain(s) F(CF2)n(CH2)m with n=4, 6, 8, 10, and m=2, 11 have been prepared by various synthetic methods, starting from the corresponding iodides or bromides. Methods based on sodium hydrogen sulfide, commonly used to accomplish this conversion, treatment of the Bunte salt obtained from sodium thiosulfate, the basic hydrolysis of isothiouronium salts, the hydrolysis under mild conditions of thiophosphorates formed from sodium thiophosphate and the basic hydrolysis of thiol acetic acid derivatives, have been investigated and compared relatively to the selective synthesis of the title compounds. The thiolacetic route yields essentially the thiols with some amounts of disulfides. Results from thiourea appears similar. Sodium thiophosphate constitutes an excellent route for the synthesis of thioethers, particularly when starting from the bromides. The two classical methods based on sodium hydrogen sulfide and sodium thiosulfate exhibit poor selectivity. It has been possible to obtain all the sulfur compounds reported in the pure state.
