221368-76-9Relevant academic research and scientific papers
Conformationally unambiguous spin labeling for distance measurements
Sajid, Muhammad,Jeschke, Gunnar,Wiebcke, Michael,Godt, Adelheid
supporting information; experimental part, p. 12960 - 12962 (2010/07/03)
An iDEER about molecular structure: Measurements of interspin distances through double electron-electron resonance (DEER) experiments allow information to be gained about the structure of molecules (see figure). The less variability in the orientation of the N-O axis of nitroxyl spin labels with respect to the labeled molecule, the smaller the distribution of the interspin distance and thus the better the conclusion.
The synthesis of novel isoindoline nitroxides bearing water-solubilising functionality
Fairfull-Smith, Kathryn E.,Brackmann, Farina,Bottle, Steven E.
experimental part, p. 1902 - 1915 (2009/09/05)
A range of novel tetramethyl- and tetraethylisoindoline nitroxides, possessing aryl-linked carboxylic acids, amines, alcohols and phosphonic acids were prepared. Notably, the chemistry established for the aromatic dibromination of the tetramethylisoindoli
PROFLUORESCENT NITROXIDE COMPOUNDS
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Page/Page column 37, (2010/11/28)
A polymeric system which includes a polymeric material and a pro-fluorescent nitroxide compound or a fluorescent spin adduct thereof, the compound having at least one 5 to 10 membered heterocyclic ring comprising a nitroxide moiety or a fluorescent spin adduct thereof and an aryl or heteroaryl group fused therewith, wherein the compound includes at least one fluorophore; with the proviso that when the heterocyclic ring has 5 carbon atoms, the aryl group cannot be an unsubstituted phenanthrene.
Brominated isoindolines: precursors to functionalised nitroxides
Micallef, Aaron S.,Bott, Raymond C.,Bottle, Steven E.,Smith, Graham,White, Jonathon M.,et al.
, p. 65 - 72 (2007/10/03)
A new, convenient method for the preparation of functionalised precursors to stable tetraalkylisoindoline nitroxides (aminoxyls) is presented. Simple treatment of 2-benzyl-1,1,3,3-tetramethylisoindoline 2 with Br2 in CCl4 gives rapid oxidative debenzylation, generating benzaldehyde and an unusual bromoamine, 2-bromo-1,1,3,3-tetramethylisoindoline 4, in high yield. Treatment of the bromoamine 4 with FeSO4-H2S04 results in bromination of the aromatic ring in varying yield, while rapid treatment with peroxide-tungstate causes debromination, generating 1,1,3,3-tetra-methylisoindoline 3. Bromination of the isoindoline aromatic ring is more readily afforded by treatment of 2-benzyl-1,1,3,3-tetramethylisoindoline 2 with Br2 and AlCl3 in CCl4, producing 2,5-dibromo-1,1,3,3-tetramethylisoindoline 7 and/or 2,5,6-tribromo-1,1,3,3-tetramethylisoindoline 6 in varying yields depending upon the exact reaction conditions. Rapid treatment with peroxide-tungstate generates the corresponding bromine substituted isoindolines, 5-bromo-1,1,3,3-tetramethylisoindoline 5 and 5,6-dibromo-1,1,3,3-tetramethylisoindoline 8. Prolonged peroxide-tungstate treatment oxidises the substituted bromoamines to the corresponding nitroxides, 5-bromo-1,1,3,3-tetramethylisoindolin-2-yloxyl 9 and 5,6-dibromo-1,1,3,3-tetramethylisoindolin-2-yloxyl 10. SQUID magnetic susceptibility measurements of crystalline 10 reveal strong antiferromagnetic interradical spin coupling. The crystal structures of 10, 2-bromo-1,1,3,3-tetramethylisoindoline 4 and the hydrobromide dihydrate salt of 1,1,3,3-tetramethylisoindoline 3 (3a) have also been determined, with 10 displaying an interesting molecular packing arrangement.
