101-67-7Relevant articles and documents
Incorporation of ring nitrogens into diphenylamine antioxidants: Striking a balance between reactivity and stability
Hanthorn, Jason J.,Valgimigli, Luca,Pratt, Derek A.
experimental part, p. 8306 - 8309 (2012/07/13)
The incorporation of nitrogen atoms into the aryl rings of conventional diphenylamine antioxidants enables the preparation of readily accessible, air-stable analogues, several of which have temperature-independent radical-trapping activities up to 200-fold greater than those of typical commercial diphenylamines. Amazingly, the nitrogen atoms raise the oxidation potentials of the amines without greatly changing their radical-trapping (H-atom transfer) reactivity.
Preparation of highly reactive pyridine- and pyrimidine-containing diarylamine antioxidants
Hanthorn, Jason J.,Valgimigli, Luca,Pratt, Derek A.
experimental part, p. 6908 - 6916 (2012/10/08)
We recently reported a preliminary account of our efforts to develop novel diarylamine radical-trapping antioxidants (Hanthorn, J. J. et al. J. Am. Chem. Soc. 2012, 134, 8306-8309) wherein we demonstrated that the incorporation of ring nitrogens into diphenylamines affords compounds which display a compromise between H-atom transfer reactivity to peroxyl radicals and stability to one-electron oxidation. Herein we provide the details of the synthetic efforts associated with that report, which have been substantially expanded to produce a library of substituted heterocyclic diarylamines that we have used to provide further insight into the structure-reactivity relationships of these compounds as antioxidants (see the accompanying paper, DOI: 10.1021/jo301012x). The diarylamines were prepared in short, modular sequences from 2-aminopyridine and 2-aminopyrimidine wherein aminations of intermediate pyri(mi)dyl bromides and then Pd-catalyzed cross-coupling reactions of the amines and precursor bromides were the key steps to yield the diarylamines. The cross-coupling reactions were found to proceed best with Pd(η3-1-PhC3H 4)(η5-C5H5) as precatalyst, which gave higher yields than the conventional Pd source, Pd2(dba) 3.
SUBSTITUTED DIARYLAMINES AND USE OF SAME AS ANTIOXIDANTS
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Page/Page column 65, (2013/02/28)
The present invention relates to substituted heteroaromatic dianlamine compounds of Formula I and II, their pharmaceutically acceptable salts, and compositions thereof useful as antioxidants, wherein each of X, Y and Z are independently a carbon or nitrogen atom; R1 and R2 are each independently a hydrogen or an electron donating group, but are not both hydrogen, and wherein R1 and R2 are each bonded to a carbon atom in their own respective aryl ring.
Self-assembly, dynamics, and phase transformation kinetics of donor-acceptor substituted perylene derivatives
Tasios, Nikos,Grigoriadis, Christos,Hansen, Michael Ryan,Wonneberger, Henrike,Li, Chen,Spiess, Hans W.,Muellen, Klaus,Floudas, George
supporting information; experimental part, p. 7478 - 7487 (2010/08/05)
The role of alkyl chain substitution on the phase formation and core dynamics is studied in a series of diphenylamine functionalized perylenemonoimides (PMIs), by X-ray scattering, calorimetry and site-specific solid-state NMR techniques. In addition, the strong dipole associated with the donor-acceptor character of the molecules allow an investigation of the dynamics with dielectric spectroscopy. The self-assembly revealed an ordered phase only in PMIs with branched alkyl chains. This phase comprises a helical stacking of molecules with a molecular twist angle of 60 . Results from solid-state NMR further pointed out the importance of intramolecular hydrogen bonding in stabilizing the intracolumnar packing within the ordered phase. Moreover, the core dynamics are frozen as revealed by the value of the dynamic order parameters and the reduced strength of dipolar relaxation. The kinetics of phase transformation from the isotropic to the ordered phase proceeds via a nucleation and growth mechanism, and the rates are dominated by the nucleation barrier. Within the isotropic phase the core dynamics display strong temperature dependence with rates that depend on the number of methylene units in the alkyl chains.
Diphenylamino and indolyl substituted pyromellitides
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, (2008/06/13)
This invention relates to 3,7-bis(disubstituted aminophenyl- or indolyl)-3,7-bis(diphenylamino)pyromellitides, 3,5-bis(disubstituted aminophenyl- or indolyl)-3,5-bis(diphenylamino)pyromellitides and mixtures thereof useful as color formers, particularly in carbonless duplicating and thermal marking systems, which are prepared by the interaction of 2,5-bis(disubstituted aminophenyl- or indolyl)carbonyl-1,4-benzenedicarboxylic acids or 2,4-bis(disubstituted aminophenyl- or indolyl)carbonyl-1,5-benzenedicarboxylic acids and mixtures thereof with diphenylamines.
