Search results for "Fluorinated"
showing 10 items of 99 documents
Oxadiazolyl-Pyridinium as Cationic Scaffold for Fluorinated Ionic Liquid Crystals
2021
The synthesis and characterization of a new class of 1,2,4-oxadiazolylpyridinium as a cationic scaffold for fluorinated ionic liquid crystals is herein described. A series of 12 fluorinated heterocyclic salts based on a 1,2,4-oxadiazole moiety, connected through its C(5) or C(3) to an N-alkylpyridinium unit and a perfluoroheptyl chain, differing in the length of the alkyl chain and counterions, has been synthesized. As counterions iodide, bromide and bis(trifluoromethane)sulfonimide have been considered. The synthesis, structure, and liquid crystalline properties of these compounds are discussed on the basis of the tuned structural variables. The thermotropic properties of this series of sa…
Oxadiazolyl-pyridines and perfluoroalkyl-carboxylic acids as building blocks for protic ionic liquids: crossing the thin line between ionic and hydro…
2012
A series of 18 samples has been prepared in order to obtain fluorinated materials as Protic Ionic Liquids (PILs). These were synthesized by appropriately mixing 1,2,4-oxadiazoles derivatised with two pyridines, or one pyridine and a fluorinated chain, and perfluoroalkyl-carboxylic acids, either mono- or dicarboxylic, leading to symmetric and non-symmetric materials. Many of them showed low melting points. However, the possibility of classifying the synthesized materials as PILs is discussed in terms of effective ionicity of the systems by the combination of Density Functional Theory (DFT) calculation and IR spectroscopy. The important outcome of our investigation is that the complete proton…
Infant exposure of perfluorinated compounds: Levels in breast milk and commercial baby food
2010
In this study, an analytical method to determine six previous termperfluorinatednext term compounds (PFCs) based on alkaline digestion and solid phase extraction (SPE) followed by liquid chromatography-quadrupole-linear ion trap mass spectrometry (LC-QqLIT-MS) was validated for the analysis of human breast milk, milk previous terminfantnext term formulas and cereals baby food. The average recoveries of the different matrices were in general higher than 70% with a relative standard deviation (RSD) lower than 21% and method limits of detection (MLOD) ranging from 1.2 to 362 ng/L for the different compounds and matrices. The method was applied to investigate the occurrence of PFCs in 20 sample…
Ionic liquid crystals based on 1,2,4-triazolium rings
2017
Ionic liquids crystals (ILCs) are a class of organic materials of great current interest. They show unique properties that can be exploited in many different fields, for example their use as solvents for extraction processes as well as electrolytes for batteries, fuel cells, dye-sensitised solar cells etc. [1-4] Moreover, in perfluorinated ILCs, the segregation of the perfluorocarbon chains promotes further self-organisation of the LC phases, adding to the materials further properties such as affinity for gases suitable for example in gas-storage. [5-7] A series of salts based on 5-(4-alkyloxyphenyl)-1,4-dimethyl-3-(perfluoroalkyl)-1,2,4-triazol-4-ium structures, differing in the length of …
Catalytic asymmetric conjugate addition of terminal alkynes to β-trifluoromethyl α,β-enones.
2014
The first enantioselective conjugate alkynylation of β-trifluoromethyl α,β-enones using terminal alkynes and a taniaphos–Cu(I) complex as catalyst is described. Ketones bearing a trifluoromethylated propargylic chiral centre in the β-position were obtained with good yields and high enantiomeric excesses (up to 99%).
Diastereoselective synthesis of 2-phenyl-3-(trifluoromethyl)piperazines as building blocks for drug discovery.
2014
The synthesis of enantiomerically pure cis- and trans-2-phenyl-3-(trifluoromethyl)piperazines is described. It involved, as the key step, a diastereoselective nucleophilic addition of the Ruppert-Prakash reagent (TMSCF3) to alpha-amino sulfinylimines bearing Ellman's auxiliary. This methodology allows an entry into hitherto unknown trifluoromethylated and stereochemically defined piperazines, key scaffold components in medicinal chemistry.
Differential reactivity of fluorinated homopropargylic amino esters vs gold(I) salts. The role of the nitrogen protecting group
2015
The reaction of several homopropargyl amino esters 4, bearing aromatic substituents and a benzyl group as nitrogen substituents, with gold(I) salts gave rise to fluorinated quinolines 6 in a tandem hydroarylation-isomerization process. On the other hand, homopropargyl amino esters 7 containing a carbamate group underwent the carbonyl addition over the triple bond in the presence of gold(I) salts, rendering fluorinated oxazines 8. The use of chiral sulfoxides allowed us to develop the asymmetric version of this protocol. This two processes complete the differential reactivity showed by these types of susbtrates, depending on the nature of the nitrogen protecting group. (C) 2014 Elsevier B.V.…
Perfluorocarbon functionalized hyaluronic acid derivatives as oxygenating systems for cell culture
2014
A set of new hyaluronic acid (HA) derivatives was obtained by binding fluorinated oxadiazole (OXA) moieties to an amino derivative of the polysaccharide (HA-EDA). The obtained HA-EDA-OXA biomaterials are potentially able to improve oxygenation into a scaffold for tissue engineering purposes. The oxygen solubility in aqueous dispersions of the obtained derivatives showed that polymers were able to improve oxygen uptake and maintenance in the medium. The HA-EDA-OXA was employed to form a hydrogel in situ by reaction with a vinyl sulphone derivative of inulin, under physiological conditions. The influence of the presence of OXA moieties on the mechanical properties of the obtained hydrogels as…
Tailor‐Made Amino Acids and Fluorinated Motifs as Prominent Traits in Modern Pharmaceuticals
2020
Structural analysis of modern pharmaceutical practices allows for the identification of two rapidly growing trends: the introduction of tailor-made amino acids and the exploitation of fluorinated motifs. Curiously, the former represents one of the most ubiquitous classes of naturally occurring compounds, whereas the latter is the most xenobiotic and comprised virtually entirely of man-made derivatives. Herein, 39 selected compounds, featuring both of these traits in the same molecule, are profiled. The total synthesis, source of the corresponding amino acids and fluorinated residues, and medicinal chemistry aspects and biological properties of the molecules are discussed.
Superhydrophobic TiO2/Fluorinated Polysiloxane Hybrid Coatings with Controlled Morphology for Solar Photocatalysis
2021
Abstract Technological applications of polysiloxane coatings have been influenced by their intrinsic low surface energy, which increases their water repellence. Accurate control of composition and interfacial properties through the introduction of perfluorinated moieties further lowers the polysiloxane surface energy, while mixing with metal oxide nanoparticles enhances roughness, resulting in a great potential in the development of superhydrophobic materials for photocatalysis. Herein, a series of hydrophobic and superhydrophobic hybrid coatings were prepared by dehydrocoupling and hydrosilylation reactions of polymethylhydrosiloxane with 1H,1H,2H,2H‐perfluorooctyltriethoxysilane and 1,3-d…