- FLUORINATED PHOSPHONIUM IONIC SALTS LINKED TO CARBENE-PRECURSORS
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Fluorinated phosphonium salts are linked to a diazirine moiety. A carbene precursor was photochemically generated from the diazirine to covalently attach the salt to substrates e.g., cotton and paper. Surface-coated substrates were found to have anti-wett
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Page/Page column 26; 30
(2013/08/15)
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- Diazirine-modified gold nanoparticle: Template for efficient photoinduced interfacial carbene insertion reactions
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Photolysis of a 3-aryl-3-(trifluoromethyl)diazirine-modified monolayer-protected gold nanoparticles (2-C12MPNs), with a core size of 1.8 ± 0.3 nm, in the presence of model carbene trapping reagents leads to efficient, essentially quantitative, modification of the interface via carbene insertion reactions. The utility of carbene insertion reactions as a general approach for the modification of Au-MPNs to provide a breadth of new structures available was demonstrated using acetic acid, methanol, benzyl alcohol, phenol, benzylamine, methyl acrylate, and styrene (10a-g, respectively) as electrophilic carbene trapping agents to form the corresponding modified 3a-g-C12MPNs. The 1.8 ± 0.3 nm gold nanoparticles bearing a diazirine group (2-C12MPNs) were synthesized using the ligand exchange reaction with the requisite 3-aryl-3-(trifluoromethyl) diazirinealkylthiol. The 2-C12MPNs and the resulting products of the reaction on the MPN (3a-g-C12MPN) were fully characterized by IR, 1H NMR, and 19F NMR spectroscopy and, when applicable, transmission electron microscopy (TEM). Verification for the 3a-g-C 12MPNs was accomplished by comparison of the spectral data to those of obtained for the photoreactions of 3-(3-methoxyphenyl)-3-(trifluoromethyl)- 3H-diazirine as a model with 10a-g.
- Ismaili, Hossein,Lee, Soo,Workentin, Mark S.
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p. 14958 - 14964
(2011/10/31)
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- Surface modification of nylon 6,6 using a carbene insertion approach
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The diazirine functionalised fluorenone, 3-[3-(trifluoromethyl)diazirin-3- yl]phenyl-9-oxo-9H-fluorene-2-carboxylate was synthesised to act as a model compound capable of modifying a wide variety of polymeric substrates. Photochemical activation of the diazirine moiety of the fluorenone derivative was utilised to afford highly reactive carbenes capable of insertion into or addition to a wide variety of functionalities. In this paper the photoinduced attachment of a fluorenone derivative to nylon 6,6 has been studied using UV-visible spectroscopic analysis. Incorporation of the fluorenone chromophore onto the backbone of nylon at different loading levels and after different coating cycles has been investigated and is detailed in this paper. the Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2006.
- Blencowe, Anton,Cosstick, Kevin,Hayes, Wayne
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- Versatile synthesis of phenoxydiazirine-based fatty acid analogues and photoreactive galactosylceramide
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A versatile synthesis of diazirine-based photoreactive fatty acid analogues is reported. The key step is phenoxy alkylation of diazirine with halo alkyl acid esters. The conditions described will be acceptable for the synthesis of various alkyl-length derivatives. The fatty acid derivatives are acceptors for reverse reactions of sphingolipid ceramide N-deacylase (SCDase), which catalyzes the condensation of psychosine and fatty acids to form photoreactive galactosylceramide. The photoreactive galactosylceramide can also be prepared with chemical synthesis, condensation of psychosine and fatty acid succinimidyl ester, and is recognized with anti-GarCer antibody both before and after irradiation.
- Hashimoto, Makoto,Hatanaka, Yasumaru,Nabeta, Kensuke
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- A Novel Family of Aromatic Diazirines for Photoaffinity Labeling
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A series of simple methods for modifying diazirines bearing an aromatic ring has been accomplished.This first versatile approach involving direct substitution on the aromatic ring of diazirines has been achieved by means of the aromatic thallation of (alkoxyphenyl)diazirines.Introduction of the thallium moiety was successfully followed by nitration, iodination, or palladium-catalyzed carbonylation to give a family of substituted aryldiazirines useful for photolabeling.For instance, diazirines labeled with a nitro group can be detected by spectrophotometric methods, and those labeled with an iodo group can be useful in tracer experiments.The (methoxyphenyl)diazirines were also found to be stable under certain demethylation conditions, thus providing a potential source of diazirines with modifiable phenol hydroxyl groups.By means of this approach, a spacer arm to link diazirines with ligands was readily introduced.Radioactive diazirines labeled with carbon-14 or tritium were also prepared using this method.All the new diazirines were derived from a pair of simple (methoxyphenyl)diazirines.The ease of derivatization of the (alkoxyphenyl)diazirines described here may offer a practical approach to simplify the time-consuming methods currently used for diazirine synthesis.
- Hatanaka, Yasumaru,Hashimoto, Makoto,Kurihara, Hiroko,Nakayama, Hitoshi,Kanaoka, Yuichi
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p. 383 - 387
(2007/10/02)
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- Syntheses of nitro-substituted aryl diazirines. An entry to chromogenic carbene precursors for photoaffinity labeling
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3-Phenyl-3-trifluoromethyl-diazirine derivatives with nitro and alkoxy substituents on their aromatic ring have been synthesized as carbene precursors for chromogenic detection of photolabeled products. Photolysis of the diazirines in methanol or cyclohex
- Hatanaka,Hashimoto,Nakayama,Kanaoka
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p. 826 - 831
(2007/10/02)
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