139613-90-4

Upstream product

• 355-43-1 n-perfluorohexyl iodide 
• 540-37-4 p-aminoiodobenzene 
• 12775-96-1 copper 
• 106-40-1 4-bromo-aniline 
• 335-56-8 1-bromo-1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane 
• 62-53-3 aniline 

Downstream Products

• 609816-25-3 N-(4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)phenyl)maleimide 
• 1384111-90-3 C₁₆H₈F₁₃NO₃ 
• 326806-93-3 N-[4-(perfluorohexyl)phenyl]-2,4-dinitrobenzenamine 
• 193197-68-1 tris(4-tridecafluoro-n-hexylphenyl)phosphine 
• 150956-62-0 4-(4-tridecafluorohexyl-phenylazo)-phenylamine 
• 149068-56-4 4-(tridecafluoro-n-hexyl)bromobenzene 

Relevant academic research and scientific papers

Reversible wettability of optothermal responsively perfluoroalkyl azobenzene self-assembled monolayers

In this study, two perfluoroalkyl azobenzene trichlorosilanes were synthesized and then characterized by Fourier transform infrared spectroscopy (FT-IR),1H NMR, and19F NMR. Subsequently, these fluorine containing trichlorosilanes were applied to form self-assembled monolayers (SAMs) on silicon substrates by the method of chemical deposition in liquid phase. The optothermal responsively isomerization of the azobenzene was achieved via UV irradiation and heat treatment. The surface structures of the SAMs were investigated by X-ray photoelectron spectroscopy (XPS), energy dispersive X-ray spectroscopy (EDS), and atomic force microscopy (AFM). The results showed that the thermal migration of the terminal fluoroalkyl groups promoted the isomerization of the azo-groups. Moreover, the reversible contact angles of the SAMs demonstrated a good reversibility of surface wettability, which was consistent with the optothermal responsive isomerization of the azo-groups.

Towards a practical perfluoroalkylation of (hetero)arenes with perfluoroalkyl bromides using cobalt nanocatalysts

A convenient methodology for perfluoroalkylation including trifluoromethylation of (hetero)arenes with perfluoroalkyl bromides was developed. Key for the success is the use of a specific cobalt-based nanocatalyst, which can be recycled at least up to 4 times. The scope of this first cobalt-catalyzed perfluoroalkylation is presented and detailed catalyst characterization (e.g. analytical STEM, XPS, and XRD) has been carried out.

A fast response photo isomerous 4-Fluoalkyl azo-phenyl propylene ether and its preparation method

The invention discloses rapid-response photoisomerization 4-perfluoroalkyl azobenzene allyl ether and a preparation method thereof. The general structural formula of 4-perfluoroalkyl azobenzene allyl ether is shown in the Specification. The preparation method includes the following steps: dissolving the starting compounds, 4-iodoaniline and fluorine-containing alkyl iodide, into a high boiling point solvent, and under the protection of nitrogen, heating, and catalyzing the solvent by copper powder to obtain fluoroalkyl aniline; after diazotizing fluoroalkyl aniline using hydrochloric acid/nitrite system at a temperature of 0-5 DEG C, enabling the diazotized solution to react with the phenol alkaline solution to obtain perfluoroalkyl azo phenol; under the protection of nitrogen, heating perfluoroalkyl azo phenol and 3-bromopropylene in an anhydrous and oxygen-free polar solvent under a weak base condition to obtain 4-fluoroalkyl azobenzene propenyl ether. The fluorine-containing azobenzene compound photoisomerization provided by the invention can response rapidly, has an active functional group propenyl, is capable of participating in addition reactions or polymerization reactions, and can be applied widely.

Synthesis and X-ray analysis of a perfluoroalkyl-substituted azobenzene dye

A search for colorants capable of reducing the surface energy of synthetic fibers as well as adding color led to the synthesis and characterization of the repellency behavior of dyes such as 4-N,N-diethylamino-4′-tridecafluorohexylazobenzene. Unexpectedly

Partitioning solvophobic and dispersion forces in alkyl and perfluoroalkyl cohesion

Fluorocarbons often have distinct miscibility properties compared to their nonfluorinated analogues. These differences may be attributed to van der Waals dispersion forces or solvophobic effects, but their contributions are notoriously difficult to separate in molecular recognition processes. Here, molecular torsion balances were used to compare cohesive alkyl and perfluoroalkyl interactions in a range of solvents. A simple linear regression enabled the energetic partitioning of solvophobic and van der Waals forces in the self-association of apolar chains. The contributions of dispersion interactions in apolar cohesion were found to be strongly attenuated in solution compared to the gas phase, but still play a major role in fluorous and organic solvents. In contrast, solvophobic effects were found to be dominant in driving the association of apolar chains in aqueous solution. The results are expected to assist the computational modelling of van der Waals forces in solution.

Materials for inducing alignment in liquid crystal and liquid crystal displays

The present invention provides novel aromatic diamines useful in preparing polyimides for optical alignment layers in liquid crystal displays. The novel compositions comprise side-chains general formula I -L1-D-L2-Cf wherein D comprises 1 to 4 carbon-carbon double bonds, Cf is a monovalent C4 to C20 fluorocarbon radical and L1 and L2 are linking groups.

Design, synthesis, application and recovery of a minimally fluorous diaryl diselenide for the catalysis of stannane-mediated radical chain reactions

The synthesis of a minimally fluorous (52% F) diaryl diselenide is described. On reduction in situ with tributylstannane this diselenide provides a fluorous selenol which is effective in inhibiting a range of stannane-mediated radical rearrangements, including a cyclopropylcarbinyl ring opening. A method for the recovery of the fluorous diselenide involving continuous extraction in a modified, cooled continuous extractor is described.

Inhibition of stannane-mediated radical rearrangements by a recoverable, minimally fluorous selenol

(equation presented) The preparation of a minimally fluorous diaryl diselenide is described. It is demonstrated that this diselenide, reduced in situ to the corresponding selenol, may be used in conjunction with stannanes to prevent a number of radical rearrangements. A 1 M solution of this selenol used in admixture with Breslow's water-soluble stannane can be used to significantly inhibit a cyclopropylcarbinyl ring opening. The combination of the fluorous selenol and the polar stannane permits recovery of the selenol by continuous fluorous extraction and isolation of a stannane-free hydrocarbon product.

Syntheses of Azobenzene Derivatives Having Fluoroalkyl Chain and Their Monomolecular Film Formation at the Air/Water Interface

The compounds, 4-(nonafluorobutyl)aniline, 4-(tridecafluorohexyl)aniline, and 4-(heptadecafluorooctyl)aniline were prepared by the reaction of corresponding perfluoroalkyl iodide with 4-iodoaniline in the presence of copper bronze.Six azobenzene derivatives (4-(4-fluorophenylazo)phenol, F(C6H4)N=N(C6H4)OH (1) (C6H4=p-phenylene), 4-(trifluoromethylphenylazo)phenol, CF3(C6H4)N=N(C6H4)OH (2), 4-(4-heptafluoropropylphenylazo)phenol, C3F7(C6H4)N=N(C6H4)OH (3), 4-(4-nonafluorobutylphenylazo)phenol, C4F9(C6H4)N=N(C6H4)OH (4), 4-(4-tridecafluorohexylphenylazo)phenol, C6F13(C6H4)N=N(C6H4)OH (5), and 4-(4-heptadecafluorooctylphenylazo)phenol, C8F17(C6H4)N=N(C6H4)OH (6)) were prepared by the usual diazo coupling reactions using 4-(perfluoroalkyl)aniline and phenol.The monomolecular film formations of the azobenzene derivatives at the air/water interface were investigated by surface pressure measurements to be dependent on the fluoroalkyl chain length (n).The compounds 5 (n=6) and 6 (n=8) formed stable monomolecular films at the air/water interface.