- Unexpected Rearrangement of 2-Bromoaniline under Biphasic Alkylation Conditions
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Alkylation of 2-bromoaniline with benzyl bromide under ostensibly basic N-alkylation conditions resulted in migration of bromine from the 2- to the 4-aryl position. Herein we report our studies to elucidate the mechanism of this rearrangement with the objective of suppressing this unexpected outcome. We find that careful choice of reagents is critical, and that this behavior may be extrapolated to alkylation reactions of electron-rich bromo- and iodoanilines in general.
- Barraza, Scott J.,Denmark, Scott E.
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supporting information
p. 2891 - 2895
(2017/10/06)
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- With near-infrared absorbing organic small molecule semiconductor material and its preparation and use
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The present invention relates to a 2,2'-(2,8-bis(dialkyl amine)-indeno [1,2-b] fluorenes-6,12-diylidene)-dimalononitrile derivative as shown in a formula I, and a preparation method and use. The compound provided by the present invention as shown in the specification is a near-infrared absorbing organic small molecule semiconductor material, which can be used as an active layer of a bipolar organic field effect transistor, an active layer of a near-infrared light detector and other optoelectronic devices.
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Paragraph 0036; 0037; 0038
(2017/08/24)
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- Aerobic photooxidative bromination of aromatic compounds using carbon tetrabromide mediated by anthraquinone-2-carboxylic acid
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We developed the aerobic photooxidative bromination of aromatic compounds using carbon tetrabromide in the presence of anthraquinone-2-carboxylic acid under visible light irradiation.
- Tanaka, Masanori,Kamito, Yuji,Lei, Cui,Tada, Norihiro,Itoh, Akichika
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p. 5886 - 5888
(2015/11/02)
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- Nanoscale phase analysis of molecular cooperativity and thermal transitions in dendritic nonlinear optical glasses
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A broad nanoscopic study of a wide-range of dendritic organic nonlinear optical (NLO) self-assembly molecular glasses reveals an intermediate thermal phase regime responsible for both enhanced electric field poling properties and strong phase stabilizatio
- Knorr, Daniel B.,Benight, Stephanie J.,Krajina, Brad,Zhang, Cheng,Dalton, Larry R.,Overney, René M.
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p. 13793 - 13805
(2013/01/16)
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- NEAR-INFRARED ABSORBING FILM COMPOSITIONS
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A curable liquid formulation containing at least (i) one or more near-infrared absorbing triphenylamine -based dyes, and (ii) one or more casting solvents. The invention is also directed to solid near- infrared absorbing films composed of crosslinked forms of the curable liquid formulation. The invention is also directed to a microelectronic substrate containing a coating of the solid near-infrared absorbing film as well as a method for patterning a photoresist layer coated on a microelectronic substrate in the case where the near-infrared absorbing film is between the microelectronic substrate and a photoresist film.
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Page/Page column 31
(2011/04/13)
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- Synthesis of N-and C-trimethylsilyl-substituded anililes
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N-Metallation of bromoanilines with ethylmagnesium bromide followed by a reaction with trimethylchlorosilane provided N-mono and N-bis(trimethylsilyl) bromoanilines depending on the structure of substrate. The metallation of bissilylated bromoanilines with butyllithium permitted the introduction of a trimethylsilyl substituent in the aromatic ring. Previously unknown 2-bromo-N,N-bis(trimethylsilyl)aniline, 2,6-dibromo-N-trimethylsilylaniline, 2,6-dibromo-N,N-bis(trimethylsilyl)aniline, 2-bromo-6-trimethylsilylaniline, 2-bromo-6-trimethylsilyl-N,N-bis(trimethylsilyl)aniline, 2-bromo-6- trimethylsilyl-N-trimethylsilylaniline, 2,4,6-tribromo-N-trimethylsilylaniline, and 2,4,6-tribromo-N,N-bis(trimethylsilyl)aniline were prepared. The structures of the compounds obtained were established by the chromato-mass spectrometry and 1H, 13C, and 29Si NMR spectroscopy.
- Storozhenko,Belyakova,Starikova,Nosova,Shulyat'eva,Frenkel',Pecherskii
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p. 892 - 897
(2008/12/20)
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- NONLINEAR OPTICAL MATERIAL COMPOSITION AND METHOD OF MANUFACTURE
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Embodiments of the present disclosure provide non-linear optical compounds and compositions comprising a silole-derivative. In an embodiment, the silole derivative comprises a chromophore including a structure represented by Formula (A): wherein each Of R
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Page/Page column 28
(2008/12/08)
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- Nonlinear optical compounds and methods for their preparation
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Nonlinear optically active compounds, methods for making nonlinear optically active compounds, compounds useful for making nonlinear optically active compounds, methods for making compounds useful for making nonlinear optically active compounds, macrostructures that include nonlinear optically active components, and devices including the nonlinear optically active compounds and the macrostructures.
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- NONLINEAR OPTICAL COMPOUNDS AND METHODS FOR THEIR PREPARATION
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Nonlinear optically active compounds, methods for making nonlinear optically active compounds, compounds useful for making nonlinear optically active compounds, methods for making compounds useful for making nonlinear optically active compounds, macrostructures tha tinclude nonlinear optically active components, and devices including the nonlinear optically active compounds and the macrostructures.
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Page 32; 14/19
(2010/02/07)
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- Synthesis and stability studies of conformationally locked 4-(diarylamino)aryl- and 4-(dialkylamino)phenyl-substituted second-order nonlinear optical polyene chromophores
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A series of chromophores with high second-order nonlinearities has been synthesized; the chromphores consist of triarylamine or dialkylarylamine donors linked by a conformationally locked polyene bridge to a dicyanomethylidene acceptor. The use of bridges
- Staub, Katrin,Levina, Galina A.,Barlow, Stephen,Kowalczyk, Tony C.,Lackritz, Hilary S.,Barzoukas, Marguerite,Fort, Alain,Marder, Seth R.
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p. 825 - 833
(2007/10/03)
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- A convenient synthetic entry into aldehydes with extended conjugation
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Variable-length donor-acceptor polyenes 1-18 were synthesized. In the key step, a polyenal was appended to an aromatic donor through nucleophilic attack of an organolithium reagent on a vinylogous amide. Yields of aldehydes and dialdehydes in the one-pot process ranged from 12-64% and depended upon number of repeat units (n=1-3) in the polyene chain.
- Friedli, Andrienne C.,Yang, Edward,Marder, Seth R.
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p. 2717 - 2730
(2007/10/03)
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- Fluorescence of Amphiphilic Hemicyanine Dyes without Free Double Bonds
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Amphiphilic hemicyanine dyes were obtained by coupling unpolar derivatives of aniline and naphthylamine, respectively, to polar derivatives of pyridinium and isoquinolinium, respectively.These dyes have no free double bond that is prone to photoisomerization.They are effective voltage-sensitive probes in biomembranes.The dyes were characterized by their spectra of absorption and by the spectra, the quantum yields, and the lifetimes of fluorescence. (i) An enhanced polarity of solvents shifts the absorption to the blue and the fluorescence to the red.The solvatochromism is described by an enhancement of the Stokes shift at an invariant 00 energy. (ii) An enhanced polarity lowers the quantum yield of fluorescence by orders of magnitude.The effect is described by an enhancement of nonradiative deactivation at an invariant radiative decay.The enhancements of the Stokes shift and of the nonradiative decay are assigned to two types of intramolecular charge-transfer that couple to polar solvents.The first one is induced by electronic excitation.The second one is induced by intramolecular twist in the excited state.The properties of the dyes in amphiphilic assemblies are discussed in terms of their properties in bulk solvents.
- Ephardt, Heinz,Fromherz, Peter
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p. 4540 - 4547
(2007/10/02)
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