126695-58-7

Usage

Uses

Used in Photofunctionalization Applications:
4-Azido-2,3,5,6-tetrafluorobenzoic acid is used as a photofunctionalization agent for polymer surfaces. Its strong absorption at 273 nm allows for efficient photochemical reactions on the surface, enabling the creation of new functional groups or the attachment of other molecules.
Used in Chemical Research:
4-Azido-2,3,5,6-tetrafluorobenzoic acid is used as a non-fluorescent heterobifunctional, photoreactive crosslinking probe in chemical research. Its photoreactive properties allow for the formation of covalent bonds between molecules upon exposure to light, making it a valuable tool for studying molecular interactions and structures.
Used in Material Science:
In the field of material science, 4-Azido-2,3,5,6-tetrafluorobenzoic acid is used for the photofunctionalization of polymer surfaces. This allows for the modification of surface properties, such as wettability, adhesion, or biocompatibility, which can be crucial for various applications, including sensors, coatings, or biomedical devices.

InChI:InChI=1/C11H4F4N4O4/c12-6-5(7(13)9(15)10(8(6)14)17-18-16)11(22)23-19-3(20)1-2-4(19)21/h1-2H2

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 122590-77-6 4-azido-2,3,5,6-tetrafluorobenzoic acid 
• 715-37-7 methyl 4-amino-2,3,5,6-tetrafluorobenzoate 
• 122590-75-4 methyl 4-azidotetrafluorobenzoate 
• 773-82-0 Pentafluorobenzonitrile 
• 652-31-3 2,3,4,5,6-pentafluorobenzamide 
• 602-94-8 Pentafluorobenzoic acid 
• 36629-42-2 methyl pentafluorobenzoate 
• 122616-98-2 4-azidotetrafluorobenzamide 

Downstream Products

• 146672-33-5 N^ε-(4-azido-2,3,5,6-tetrafluorobenzoyl)-N^α-Boc-L-lysine 
• 158871-73-9 C₇₁H₄F₄N₂O₄ 
• 215873-25-9 (C₄H₄NO₂OOC)C₆F₄NP(C₆H₅)2CH₂P(C₆H₅)2 
• 254968-74-6 12-[N-(4-azido-2,3,5,6-tetrafluorobenzoyl)]amidododecanoic acid 
• 864970-78-5 4-azido-2,3,5,6-tetrafluoro-benzoic acid 11-carboxy-undecyl ester 
• 146672-31-3 N^ε-(4-azido-2,3,5,6-tetrafluorobenzoyl)-L-lysine 
• 146690-73-5 succinimidyl N^α-biotinyl-N^ε-(4-azido-2,3,5,6-tetrafluorobenzoyl)-L-lysinate 
• 960500-67-8 C₂₀H₁₇F₄N₉O₇S 

Relevant academic research and scientific papers

Design and synthesis of a highly efficient labelling reagent for incorporation of tetrafluorinated aromatic azide into proteins

Chemical labelling can significantly extend the structures and functions of proteins for advanced applications. Herein, a highly efficient bench-stable reagent diazo-azide was designed and synthesized for the incorporation of tetrafluorinated aromatic azi

Chemistry of bifunctional photoprobes. 6. Synthesis and characterization of high specific activity metalated photochemical probes: Development of novel rhenium photoconjugates of human serum albumin and Fab fragments

Functionalization of perfluoro aryl azides by bifunctional chelating agents (BFCAs) capable of forming high specific activity complexes with 99mTc (for γ-imaging) and 188Re (for radiotherapy) is described. The synthesis of multidonor BFCAs containing N2S2, N4, and N3S donor groups containing imidazole, pyridine, and pyrazine functionalities that may be important for tuning the pharmacokinetic parameters is also described. Functionalization of perfluoro aryl azides at various sites on BFCAs yields novel bifunctional photolabile chelating agents (BFPCAs) that are useful for covalent attachment to biomolecules. A representative Re-BFPCA 8a in a model solvent, diethylamine, proceeded to give a high yield of intermolecular NH insertion product without the decomplexation of the metal ion from 8a. All products originated from the photolysis of 8a in diethylamine are characterized by analytical techniques, and a plausible mechanism of formation of different photolytic products is suggested. The high yield of intermolecular NH insertion of Re-BFPCA 8a is extended to labeling of human serum albumin (HSA) and Fab fragments under aqueous conditions. The photolabeling technology developed here offers a new way to attach diagnostically and therapeutically useful radiotracers (e.g., 99mTc, 188Re) to Fab fragments for potential noninvasive imaging and therapy of cancer.

Differentiating p Interactions by Constructing Concave/Convex Surfaces Using a Bucky Bowl Molecule, Corannulene in Liquid Chromatography

Convex-concave p conjugated surfaces in hemispherical bucky bowl such as corannulene (Crn) have shown increasing utility in constructing self-assembled new functional materials owing to its unique p electrons and strong dipole. Here, we investigate these specific molecular recognitions on Crn by developing new silica-monolithic capillary columns modified with Crn and evaluating their performance in the separation of different aromatic compounds by liquid chromatography (LC). We synthesized two Crn derivatives and conjugated them onto the surface of a silica monolith. The first Crn derivative was edge functionalized, which can undergo free inversion of a convex-concave surface. The second Crn derivative was synthesized by modifying the spoke of Crn, which suppresses the convex-concave inversion. Results of LC suggest that each surface showed different shape recognition based on p interaction. Furthermore, the concave surface of Crn showed strong CH-p interaction with a planar molecule, coronene, demonstrated by the shifts of the1H NMR signals of both Crn and coronene resulting from the multiple interactions between Crn and p electrons in coronene. These results clearly demonstrated the presence of CH-p interactions at multiple points, and the role of shape recognition.

A Potent Halogen-Bonding Donor Motif for Anion Recognition and Anion Template Mechanical Bond Synthesis

The covalent attachment of electron deficient perfluoroaryl substituents to a bis-iodotriazole pyridinium group produces a remarkably potent halogen bonding donor motif for anion recognition in aqueous media. Such a motif also establishes halogen bonding anion templation as a highly efficient method for constructing a mechanically interlocked molecule in unprecedented near quantitative yield. The resulting bis-perfluoroaryl substituted iodotriazole pyridinium axle containing halogen bonding [2]rotaxane host exhibits exceptionally strong halide binding affinities in competitive 50 % water containing aqueous media, by a factor of at least three orders of magnitude greater in comparison to a hydrogen bonding rotaxane host analogue. These observations further champion and advance halogen bonding as a powerful tool for recognizing anions in aqueous media.

Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction

We report a fast Staudinger reaction between perfluoroaryl azides (PFAAs) and aryl phosphines, which occurs readily under ambient conditions. A rate constant as high as 18 m?1 s?1 was obtained between methyl 4-azido-2,3,5,6-tetrafluorobenzoate and methyl 2-(diphenylphosphanyl)benzoate in CD3CN/D2O. Furthermore, the iminophosphorane product was stable toward hydrolysis and aza-phosphonium ylide reactions. This PFAA Staudinger reaction proved to be an excellent bioothorgonal reaction. PFAA-derivatized mannosamine and galactosamine were successfully transformed into cell-surface glycans and efficiently labeled with phosphine-derivatized fluorophore-conjugated bovine serum albumin.

Universal Scalable and Cost-Effective Surface Modifications

Disclosed are fouling resistant filtration membranes comprising a polymeric thin-film membrane comprising a surface. Also disclosed are methods of modifying thin-film filtration membranes, thereby improving, for example, the anti-fouling properties of the membranes. Also disclosed are methods of purifying water using the disclosed membranes. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

Unique Separation Behavior of a C60 Fullerene-Bonded Silica Monolith Prepared by an Effective Thermal Coupling Agent

Herein, we report a newly developed C60 fullerene-bonded silica monolith in a capillary with unique retention behavior due to the structure of C60 fullerene. N-Hydroxysuccinimide (NHS)-conjugated C60 fullerene was successfully synthesized by a thermal coupling agent, perfluorophenyl azide (PFPA), and assigned by spectroscopic analyses. Then, NHS-PFPA-C60 fullerene was attached onto the surface of a silica monolith in a capillary. The capillary provided specific separation ability for polycyclic aromatic hydrocarbons in liquid chromatography by an effective π-π interaction. Furthermore, corannulene, which has a hemispherical structure, was selectively retained in the capillary based on the specific structural recognition due to the spherical C60 fullerene. This is the first report revealing the spherical recognition ability by C60 fullerene in liquid chromatographic separation. Spherical recognition: A C60 fullerene-bonded silica monolithic medium was prepared by using a thermal coupling agent conjugated with C60 fullerene. The C60 fullerene-bonded monolith prepared in a capillary showed a very strong π-π interaction in liquid chromatography. Also, the hemispherical molecule corannulene was dramatically retained in the C60 fullerene-bonded monolith by the unique molecular recognition based on a buckyball (see figure).

Towards a biocompatible artificial lung: Covalent functionalization of poly(4-methylpent-1-ene) (TPX) with cRGD pentapeptide

Covalent multistep coating of poly(methylpentene), the membrane material in lung ventilators, by using a copper-free "click" approach with a modified cyclic RGD peptide, leads to a highly biocompatible poly(methylpentene) surface. The resulting modified membrane preserves the required excellent gas-flow properties while being densely seeded with lung endothelial cells.

Polyurethane (PU)-derived photoactive and copper-free clickable surface based on perfluorophenyl azide (PFPA) chemistry

The anchoring and capturing roles of perfluorophenyl azide (PFPA) were combined to produce a universal polyurethane (PU)-derived photoactive surface platform (PU-1-PFPA). The resultant platform was confirmed by contact angle, attenuated total reflectance Fourier transform infrared (ATR FT-IR) spectroscopy, atomic force microscopy (AFM) and X-ray photoelectron spectroscopy (XPS) analyses. Upon UV light activation, native heparin was coupled directly onto PU-1-PFPA to yield a substrate with antithrombogenic properties. The same level of antithrombogenic activity was achieved when the recovered heparin was photo-coupled onto PU-1-PFPA. In addition, at room temperature and in the absence of copper catalysts, PU-1-PFPA achieved oriented immobilization of functional moieties bearing an alkynyl functional group.

Tri- and tetravalent photoactivable cross-linking agents

A modular synthesis of photoactivable cross-linking agents is described, using an aromatic core, di- or triethyleneglycol spacers and photoaffinity labeling synthons that feature either perfluorophenyl azide or aryl(trifluoromethyl)diazirine motifs. Symmetrical and nonsymmetrical trivalent structures were obtained from phloroglucinol and dopamine, respectively. Symmetrical tetravalent structures resulted from the coupling of two dopamine derivatives with oxalyl chloride. Georg Thieme Verlag Stuttgart New York.