122590-75-4Relevant articles and documents
A Potent Halogen-Bonding Donor Motif for Anion Recognition and Anion Template Mechanical Bond Synthesis
Bunchuay, Thanthapatra,Docker, Andrew,Martinez-Martinez, Antonio J.,Beer, Paul D.
, p. 13823 - 13827 (2019)
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.
A general method for the fabrication of graphene-nanoparticle hybrid material
Park, Jaehyeung,Jayawardena, H. Surangi N.,Chen, Xuan,Jayawardana, Kalana W.,Sundhoro, Madanodaya,Ada, Earl,Yan, Mingdi
, p. 2882 - 2885 (2015)
We describe a simple and general approach to conjugate nanoparticles on pristine graphene. The method takes advantage of the high reactivity of perfluorophenyl nitrene towards the C=C bonds in graphene, where perfluorophenyl azide-functionalized nanoparticles are conjugated to pristine graphene through the [2+1] cycloaddition reaction by a fast photoactivation.
Polyurethane (PU)-derived photoactive and copper-free clickable surface based on perfluorophenyl azide (PFPA) chemistry
Li, Lingdong,Li, Jiang,Kulkarni, Abhilash,Liu, Song
, p. 571 - 582 (2013)
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.
Towards a biocompatible artificial lung: Covalent functionalization of poly(4-methylpent-1-ene) (TPX) with cRGD pentapeptide
Moeller, Lena,Hess, Christian,Palecek, Jiri,Su, Yi,Haverich, Axel,Kirschning, Andreas,Draeger, Gerald
, p. 270 - 277 (2013)
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.
Synthesis of nitrophenyl and fluorophenyl azides and diazides by SNAr under phase-transfer or microwave irradiation: Fast and mild methodologies to prepare photoaffinity labeling, crosslinking, and click chemistry reagents
Leyva, Elisa,Aguilar, Johana,González-Balderas, Regina M.,Vega-Rodríguez, Sarai,Loredo-Carrillo, Silvia E.
, (2020/12/01)
Two fast and mild methodologies to prepare nitrophenyl and fluorophenyl azides are presented. These aryl azides are extensively used as crosslinking, photoaffinity labeling, and click chemistry reagents. Substituted aryl azides are prepared by performing a SNAr substitution on halogenated benzenes with a phase-transfer catalyst (PTC) such as tetraethylammonium tetrafluoroborate (TEATFB), the reaction proceeds in several hours under rather mild temperatures (25°C to 70°C). Furthermore, aryl azides are also prepared within minutes under microwave irradiation at slightly higher temperatures (50°C to 70°C). These procedures could be applied in the preparation of other aryl azides. In the case of substituted pentafluoro benzene (pF), the type of products obtained in each reaction depends on the amount of sodium azide and the strength and position of electron-withdrawing substituents (COH, COR, COOR, CN, NO2, or F). A discussion on the mechanisms and the products obtained in these SNAr reactions is presented.
Iron (III)-porphyrin Complex FeTSPP as an efficient catalyst for synthesis of tetrazole derivatives via [2?+?3]cycloaddition reaction in aqueous medium
El-Remaily, Mahmoud Abd El Aleem Ali Ali,Elhady
, (2019/06/08)
The metal complex (5,10,15,20-tetrakis-(4-sulfonatophenyl)-porphyrin-iron (III) chloride (FeTSPP) was new employed in an environmentally benign protocol as an efficient catalyst for a “click” chemistry approach for the synthesis of tetrazole and guanindinyltetrazole derivatives via [2?+?3] cycloaddition reaction of nitriles and azide derivatives in aqueous medium. The synthesized compounds were obtained in excellent yield, short reaction times and a recoverable catalyst.
