- Perovskite Solar Cells Based on Oligotriarylamine Hexaarylbenzene as Hole-Transporting Materials
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A cobalt-catalyzed cyclotrimerization of bis(aryl)alkyne is used as an innovative tool to obtain hole-transport materials (HTMs). The novel HTM containing six units of oligotriarylamine (HAB1), characterized by UV-vis, cyclic voltammetry, DFT, and thermogravimetric analysis, confirms its suitability as an efficient HTM in PSCs. A PCE of 17.5% was obtained in HAB1-containing PSCs, a performance comparable to that obtained with spiro-OMeTAD and with slightly better thermal stability.
- Shasti, Mona,V?lker, Sebastian F.,Collavini, Silvia,Valero, Silvia,Ruipérez, Fernando,Mortezaali, Abdollah,Zakeeruddin, Shaik. M.,Gr?tzel,Hagfeldt,Delgado, Juan Luis
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Read Online
- Effect of triptycene unit on the performance of porphyrin-based dye-sensitized solar cells
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Triptycene has been first introduced into porphyrin sensitizers (JY74 and JY75) for dye sensitized solar cells. Compared to reference dye YD26, the homoaromatic electron delocalization of triptycene makes the designed dyes a broadened absorption. Meanwhile, the rigid shape-persistent character of triptycene endows JY74 and JY75 an improved ability to diminish the charge recombination between electrolyte and semiconductor TiO2. As a result, after structural modification, larger short-circuit current and higher open-circuit voltage are achieved for dyes JY74 and JY75. The power conversion efficiency of JY75 is increased by 26.8 % compared to that of YD26. Consequently, triptycene may be a promising bulky steric hindrance group for decorating photosensitizer to get an attractive photovoltaic performance.
- Yan, Mao,Wang, Qun-Hui,Zhu, Yi-Zhou,Han, Ming-Liang,Yan, Yi-Qiao,Zheng, Jian-Yu
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Read Online
- DMSO-allyl bromide: A mild and efficient reagent for atom economic one-pot: N -allylation and bromination of 2°-aryl amines, 2-aryl aminoamides, indoles and 7-aza indoles
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A mixture DMSO-allyl bromide has been developed as a reagent for an atom economic one-pot N-allylation and aryl bromination under basic conditions. Utilizing this reagent, N-allylation-bromination of a number of 2°-aryl amines, aryl aminoamides, indoles, and 7-aza indoles has been achieved. The scope of the substrates and limitations, the synthetic utility of the products, and a plausible reaction mechanism have been proposed.
- Kannadasan, Sathananthan,Novanna, Motakatla,Shanmugam, Ponnusamy,Smile, Suresh Snoxma
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p. 1834 - 1839
(2022/02/07)
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- Supramolecular Polymerization of Triarylamine-Based Macrocycles into Electroactive Nanotubes
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A S6-symmetric triarylamine-based macrocycle (i.e., hexaaza[16]paracyclophane), decorated with six lateral amide functions, is synthesized by a convergent and modular strategy. This macrocycle is shown to undergo supramolecular polymerization in o-dichlorobenzene, and its nanotubular structure is elucidated by a combination of spectroscopy and microscopy techniques, together with X-ray scattering and molecular modeling. Upon sequential oxidation, a spectroelectrochemical analysis of the supramolecular polymer suggests an extended electronic delocalization of charge carriers both within the macrocycles (through bond) and between the macrocycles along the stacking direction (through space).
- Gavat, Odile,Giuseppone, Nicolas,Lehn, Jean-Marie,Maaloum, Mounir,Moulin, Emilie,Picini, Flavio,Schneider, Susanne,Strub, Jean-Marc,Tan, Junjun,Tokunaga, Shoichi,Vargas Jentzsch, Andreas
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supporting information
p. 6498 - 6504
(2021/05/06)
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- High-Throughput Mass Spectrometry Screening Platform for Discovering New Chemical Reactions under Uncatalyzed, Solvent-Free Experimental Conditions
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A gas-phase high-throughput reaction screening platform was developed for the first time to study chemical structures of closely related functional groups and for the discovery of novel organic reaction pathways. Experiments were performed using the contained atmospheric pressure chemical ionization (APCI) source that enabled nonthermal, nonequilibrium plasma chemistry to be monitored by mass spectrometry (MS) in real time. This contained-APCI MS platform allowed an array of reagents to be tested, resulting in the studies of multiple gas-phase reactions in parallel. By exposing headspace vapor of the selected reagents to corona discharge, solvent-free Borsche-Drecsel cyclization reaction, Katritzky chemistry, and Paal-Knorr pyrrole synthesis were examined in the gas phase, outside the high vacuum environment of the mass spectrometer. A new radical-mediated hydrazine coupling reaction was also discovered, which provided a selective pathway to synthesize secondary amines without using a catalyst. The mechanisms of these atmospheric pressure gas-phase reactions were explored through the direct capture of intermediates and via comparison with the corresponding bulk solution and droplet-phase reactions.
- Kulyk, Dmytro S.,Amoah, Enoch,Badu-Tawiah, Abraham K.
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p. 15025 - 15033
(2020/12/01)
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- PYRENE DERIVATIVES AND ORGANIC ELECTRO LUMINESCENT DEVICE COMPRISING SAME
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The present invention relates to a pyrene based derivative compound of an asymmetric structure and an organic electroluminescent device comprising the same. The pyrene derivative according to the present invention is characterized by being represented by chemical formula A through chemical formula B. The pyrene derivative compound according to the present invention exhibits remarkably improved blue color purity as compared to an organic electroluminescent device using an existing pyrene based aryl amine derivative compound while being able to realize full color since life characteristic and luminance characteristic are excellent, thereby being able to be used in various display devices.
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Paragraph 0539-0543
(2020/04/10)
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- Asymmetric pyrene derivatives comprising heteroaryl amine group and organic light-emitting diode including the same
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The present invention relates to a pyrene derivative represented by [chemical formula A] or [chemical formula B], and an organic light emitting diode comprising the same, wherein substituents Py, Het_1 to Het_3, Z, and m are defined in the detailed description of the invention.
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Paragraph 0281-0285
(2020/12/16)
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- Organic electroluminescent compounds and organic electroluminescent device using the same
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The present invention relates to an organic electroluminescent compound applied to a hole transfer material, which is characterized by being presented by chemical formula 1-1 and chemical formula 1-2. The organic electroluminescent compound according to the present invention can manufacture an organic electroluminescent device having improved light emitting efficiency and life properties, when applied to a hole transfer layer of the organic electroluminescent device.
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Paragraph 0324-0329
(2020/12/15)
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- Tuning the Photophysical Properties of Symmetric Squarylium Dyes: Investigation on the Halogen Modulation Effects
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A series of symmetric squarylium dyes (SQDPA-X) with different halogen (X=F, Cl, Br, I) substituents have been developed. The photophysical properties could be facilely tuned by the halogen modulation effects. The strategy of incorporating different halogen substitutions into AIE active luminogens enables a facile approach for exploring new intriguing organic fluorescent dyes.
- Chen, Weiben,Zhang, Simeng,Dai, Gaole,Chen, Ying,Li, Miao,Zhao, Xiaoyu,Chen, Yulan,Chen, Long
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supporting information
p. 469 - 473
(2019/01/04)
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- Dopant-Free Hole-Transporting Polymers for Efficient and Stable Perovskite Solar Cells
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A series of novel polymers (P1-P6) derived from the combination of different units (including thiophene, triarylamine, and spirobifluorene) were successfully synthesized, completely characterized, and used as hole-transporting materials (HTMs) for perovskite solar cells (PSCs). Solar cells with some of these materials as HTMs showed very good performances of almost 13% (12.75% for P4 and 12.38% for P6) even without additives, and devices based on these new HTMs show relatively improved stability against temperature compared to those based on PTAA. The presence of dopant additives has been linked to long-term degradation, which is the main barrier to the large-scale commercialization of this innovative type of solar cell. Obtaining efficient PSCs without using dopants could represent a further step toward improvement of long-term stability and thus their introduction into the market.
- Valero, Silvia,Collavini, Silvia,V?lker, Sebastian F.,Saliba, Michael,Tress, Wolfgang R.,Zakeeruddin, Shaik M.,Gr?tzel, Michael,Delgado, Juan Luis
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p. 2243 - 2254
(2019/03/19)
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- A green and mild procedure to selective synthesis of diarylamine via domino reaction of aryl halides and arginine catalyzed by magnetic-MOF
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Efficient and selective direct synthesis of diarylamines from aryl halides and arginine as a nitrogen-donor reagent is reported. Arginine, which is an oral supplement, acts as a useful nitrogen source donor in the copper-catalyzed reaction. Fe3O4/Cu3(BTC)2, which was easily separated and recycled with a magnet, improved the rate and facilitation of the synthesis of diarylamines selectively. The introduction of a new and available N-source, simple magnetic separation process, normal atmospheric conditions, and excellent yields under mild reaction conditions are other important features of this work.
- Soleiman-Beigi, Mohammad,Mohammadi, Fariba
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- Synthesis of acridines through alkyne addition to diarylamines
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A new synthesis of substituted acridines is achieved by palladium-catalyzed addition of terminal acetylenes between the aryl rings of bis(2-bromophenyl)amine. By including a diamine base and elevating the temperature, the reaction pathway favors the formation of acridine over a double Sonogashira reaction to form bis(tolan)amine. This method is demonstrated with several aryl-alkynes and alkyl-alkynes.
- Berger, Kristen E.,McCormick, Grant M.,Jaye, Joseph A.,Rozeske, Christina M.,Fort, Eric H.
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supporting information
(2018/11/24)
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- Copper immobilized at a covalent organic framework: An efficient and recyclable heterogeneous catalyst for the Chan-Lam coupling reaction of aryl boronic acids and amines
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A polyimide covalent organic framework (PI-COF) with high thermal and chemical stabilities has been readily prepared from commercially available and inexpensive reagents and was employed as an effective support for heterogeneous copper. It was demonstrated that the obtained Cu@PI-COF is a highly active heterogeneous catalyst which can effectively promote the Chan-Lam coupling reaction of aryl boronic acids and amines in an open flask without the aid of any base or additive. In addition, the catalyst could be readily recovered from the reaction mixture by simple filtration and reused for at least eight cycles without any observable change in structure and catalytic activity.
- Han, Yi,Zhang, Mo,Zhang, Ya-Qing,Zhang, Zhan-Hui
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p. 4891 - 4900
(2018/11/21)
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- Self-assembly of supramolecular fractals from generation 1 to 5
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In the seeking of molecular expression of fractal geometry, chemists have endeavored in the construction of molecules and supramolecules during the past few years, while only a few examples were reported, especially for the discrete architectures. We herein designed and constructed five generations of supramolecular fractals (G1-G5) based on the coordination-driven self-assembly of terpyridine ligands. All the ligands were synthesized from triphenylamine motif, which played a central role in geometry control. Different approaches based on direct Sonogashira coupling and/or (tpy-Ru(II)- tpy) connectivity were employed to prepare complex Ru(II)-organic building blocks. Fractals G1-G5 were obtained in high yields by precise coordination of organic or Ru(II)-organic building blocks with Zn(II) ions. Characterization of those architectures were accomplished by 1D and 2D NMR spectroscopy, electrospray ionization mass spectrometry (ESI-MS), traveling-wave ion mobility mass spectrometry (TWIM-MS), and transmission electron microscopy (TEM). Furthermore, the two largest fractals also hierarchically self-assemble into ordered supramolecular nanostructures either at solid/liquid interface or in solution on the basis of their well-defined scaffolds.
- Wang, Lei,Liu, Ran,Gu, Jiali,Song, Bo,Wang, Heng,Jiang, Xin,Zhang, Keren,Han, Xin,Hao, Xin-Qi,Bai, Shi,Wang, Ming,Li, Xiaohong,Xu, Bingqian,Li, Xiaopeng
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supporting information
p. 14087 - 14096
(2018/10/20)
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- Novel organic compounds derivatives and organic light-emitting diode therewith
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The present invention relates to an organic compound represented by the chemical formula (A) or (B) and to an organic light-emitting device comprising the same. In the chemical formulas (A) and (B), R_1 to R_14, L1, L2, Ar1 to Ar3, n and m are as described in detailed description of the invention. The first object of the present invention is to provide the organic compound having a specific structure capable of having high efficiency, low voltage and long life characteristics by using the compound in an electron transporting layer or a hole transporting layer in the organic light emitting device.COPYRIGHT KIPO 2018
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Paragraph 0510; 0594-0600
(2018/05/03)
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- Novel organic compounds and organic light-emitting diode therewith
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The present invention relates to an organic compound represented by the chemical formula A or B, and to an organic light-emitting diode comprising the same, and in the chemical formula A and the chemical formula B, R1 to R12, L1, L2, Ar1 to Ar3, n and m are as described in the description of the invention. Accordingly, a first technical object of the present invention is to provide a specific structure of organic compound having high efficiency, low voltage and long life characteristics by using the compound in an emitting layer, an electron transporting layer or a hole transporting layer in the organic light emitting diode.COPYRIGHT KIPO 2018
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Paragraph 0548-0552
(2018/05/03)
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- Chemoselective Deprotection of Sulfonamides under Acidic Conditions: Scope, Sulfonyl Group Migration, and Synthetic Applications
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Chemoselective acidic hydrolysis of sulfonamides with trifluoromethanesulfonic acid has been evaluated as a deprotection method and further extended to more complex synthetic applications. In contrast to conventional troublesome sulfonamide hydrolysis, a near-stoichiometric amount of acid was found to be sufficient to bring about efficient deprotection of various neutral or electron-deficient N-arylsulfonamides, whereas electron-rich substrates provided sulfonyl group migration products. The deprotection method developed is fully selective for N-arylsulfonamides, and the possibility to discriminate among various different sulfonamides is demonstrated.
- Javorskis, Tomas,Orentas, Edvinas
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p. 13423 - 13439
(2017/12/26)
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- Meta - And para -Functionalized Thermally Crosslinkable OLED-Materials through Selective Transition-Metal-Catalyzed Cross-Coupling Reactions
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Herein, a synthetic approach using selective transition-metal-catalyzed cross-coupling reactions to thermally crosslinkable OLED materials based on vinyl-functionalized arylamines is reported. In a modular approach, 9,9-dialkyl-2,7-diiodo-9 H -fluorene underwent a selective Ullmann cross-coupling reaction with bromo-substituted-diphenylamines to give 9,9-dialkyl-2,7-bis(bromo-substituted-diphenylamino)-9 H -fluorenes that underwent end-functionalization by the Suzuki-Miyaura reaction using potassium vinyltrifluoroborate to give the corresponding 9,9-dialkyl-2,7-bis(vinyl-substituted-diphenylamino)-9 H -fluorenes. Novel meta -functionalized materials were synthesized, which are difficult to prepare by traditional synthetic pathways. The thermal behavior of the compounds was investigated by DSC measurements, indicating a lower thermal sensitivity of the meta -substituted materials than their para -functionalized analogues.
- Hempe, Matthias,Schnellb?cher, Lutz,Wiesner, Tobias,Reggelin, Michael
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p. 4489 - 4499
(2017/09/26)
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- A search for blues brothers: X-ray crystallographic/spectroscopic characterization of the tetraarylbenzidine cation radical as a product of aging of solid magic blue
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Magic blue (MB+? SbCl6- salt), i.e. tris-4-bromophenylamminium cation radical, is a routinely employed one-electron oxidant that slowly decomposes in the solid state upon storage to form so called 'blues brothers', which often complicate the quantitative analyses of the oxidation processes. Herein, we disclose the identity of the main 'blues brother' as the cation radical and dication of tetrakis-(4-bromophenyl)benzidine (TAB) by a combined DFT and experimental approach, including isolation of TAB+? SbCl6- and its X-ray crystallography characterization. The formation of TAB in aged magic blue samples occurs by a Scholl-type coupling of a pair of MB followed by a loss of molecular bromine. The recognition of this fact led us to the rational design and synthesis of tris(2-bromo-4-tert-butylphenyl)amine, referred to as 'blues cousin' (BC: Eox1 = 0.78 V vs. Fc/Fc+, λmax(BC+?) = 805 nm, εmax = 9930 cm-1 M-1), whose oxidative dimerization is significantly hampered by positioning the sterically demanding tert-butyl groups at the para-positions of the aryl rings. A ready two-step synthesis of BC from triphenylamine and the high stability of its cation radical (BC+?) promise that BC will serve as a ready replacement for MB and an oxidant of choice for mechanistic investigations of one-electron transfer processes in organic, inorganic, and organometallic transformations.
- Talipov, Marat R.,Hossain, Mohammad M.,Boddeda, Anitha,Thakur, Khushabu,Rathore, Rajendra
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supporting information
p. 2961 - 2968
(2016/03/12)
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- Imide-containing aromatic diamine compound of the structure and its preparation method and application
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The invention discloses an aromatic diamine compound containing an imide structure as well as a preparation method and application thereof. The method for preparing the aromatic diamine compound containing the imide structure comprises the following steps of: preparing a rigid non-planar distorted structural intermediate containing the imide structure by high reaction activity of acyl chloride and active hydrogen; introducing different chemical groups through the Suzuki reaction of halogen elements and boric acid ester; utilizing fluoronitrobenzene to react with amino so as to preparing a binitro product by reaction of fluoronitrobenzene and amino; and reducing to obtain a novel aromatic diamine compound containing the imide structure. The synthesizing method is simple, easy to purify and high in yield; the synthesized compound has unique fluorescent characteristic, excellent thermal property and solubility property, can be used as a photoelectric material and a monomer for synthesizing novel high-performance polymers such as polyamide, polyimide, polyamide imide and polyester imide.
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Paragraph 0046; 0048-0050
(2016/12/16)
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- Investigation of pyrolysis temperature in the one-step synthesis of L10 FePt nanoparticles from a FePt-containing metallopolymer
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Ferromagnetic (L10 phase) FePt alloy nanoparticles (NPs) with extremely high magnetocrystalline anisotropy are considered to be very promising candidates for the next generation of ultrahigh-density data storage systems. The question of how to generate L10 FePt NPs with high coercivity, controllable size, and a narrow size distribution is a challenge. We report here a single-step fabrication of L10 FePt NPs by employing one of the two new polyferroplatinyne bimetallic polymers as precursors. The influence of the pyrolysis temperature on the size and magnetic properties of the resulting FePt alloy NPs has been investigated in detail.
- Dong, Qingchen,Li, Guijun,Wang, Hua,Wing-Tat Pong, Philip,Leung, Chi-Wah,Manners, Ian,Ho, Cheuk-Lam,Li, Hua,Wong, Wai-Yeung
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p. 734 - 741
(2015/07/27)
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- Novel aromatic amine compounds for organic light-emitting diode and organic light-emitting diode including the same
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The present invention relates to an organic light emitting compound represented by the chemical formula A or the chemical formula B and an organic light emitting diode comprising the same, wherein A1 to A3, X, Y, and Z are the same as defined in the specification.COPYRIGHT KIPO 2016
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Paragraph 0452-0457
(2016/10/10)
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- Quinoxaline derivative, and light emitting element, light emitting device, and electronic appliance using the same
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Generally below the type (1) represented by general quinoxaline derivatives is provided. (Said in formula, R 1 ～ R 12 each is hydrogen atom, halogen atom, alkyl, alkoxy group, an acyl group, d alkyl amino , diaryl reel amino , substituted or unsubstituted vinyl, , or a substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group shows 0 and, Ar 1 substituted or group, or a substituted or unsubstituted non-phenyl roof tile substituted or unsubstituted phenyl shows 0 and, Ar 2 the substituted or unsubstituted phenyl, substituted or unsubstituted ITO-glass substrate, substituted or unsubstituted phenyl , substituted or unsubstituted only annularity heterocyclic group, or a substituted or. shows 0.)
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Paragraph 0290; 0291; 0292; 0293; 0294
(2016/11/02)
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- Practical synthesis of aromatic dithiocarbamates
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Oxidation-sensitive N,N-diaryl dithiocarbamates (DTCs) are synthesized in good yields by the generation of metal amide salts from N-benzoyl precursors, followed by addition of CS2. para-Substituted diphenylamines are prepared by electrophilic aromatic substitution of diphenylbenzamide and saponification. Deacylation of electron-rich species such as bis(p-dimethylaminophenyl)benzamide is challenging because of the oxidative sensitivity of the anionic intermediate but could be achieved in good yield by using n-BuLi to generate a hemiaminal adduct, prior to acidification. The N,N-diaryl DTCs are stable as alkali salts and can be used to produce densely packed monolayers on gold surfaces. Copyright
- Padungros, Panuwat,Wei, Alexander
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p. 2336 - 2343
(2014/07/22)
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- Synthesis of benzo-γ-sultams via the Rh-catalyzed aromatic C-H functionalization of diazosulfonamides
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An efficient synthesis of 1-aryl-benzo-γ-sultams, 1-aryl-1,3-dihydrobenzo[c]isothiazole-2,2-dioxides, was achieved in 65-99% yields via the Rh-catalyzed intramolecular aromatic C-H functionalization of N,N-diaryl diazosulfonamides with 0.5 mol% Rh2(oct)4 as the catalyst. This journal is the Partner Organisations 2014.
- Yang, Zhanhui,Xu, Jiaxi
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supporting information
p. 3616 - 3618
(2014/04/03)
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- A facile, regioselective and controllable bromination of aromatic amines using a CuBr2/Oxone system
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A combination of cupric bromide and Oxone serves as a facile, mild and effective reagent for the bromination of aromatic amines. Primary, secondary and tertiary aromatic amines are all suitable substrates. The reaction possesses high regioselectivity and functional group tolerance, and mono- and multi-brominated products can be obtained controllably in moderate to excellent yields. The Royal Society of Chemistry 2013.
- Li, Xin-Le,Wu, Wei,Fan, Xin-Heng,Yang, Lian-Ming
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p. 12091 - 12095
(2013/09/02)
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- The synthesis and photovoltaic properties of A-D-A-type small molecules containing diketopyrrolopyrrole terminal units
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A series of novel A-D-A structured small molecule photovoltaic (PV) materials [CZ(TDPP)2, DPA(TDPP)2, PTZ(TDPP)2 and FL(TDPP)2] with diketopyrrolopyrrole (DPP) as an electron-withdrawing group were synthesized and characterized. These small molecular donors exhibit excellent solubility in common organic solvents. The density functional theory (DFT) calculations demonstrated the intramolecular charge transfer (ICT) behavior of the synthesized PV materials and an efficient charge separation was observed by a fluorescence quenching experiment. In addition, their photophysical and electrochemical properties show that they harvest sunlight over the entire visible spectrum range and keep appropriate energy levels to satisfy the requirement of solution-processable OSCs. Therefore, we explored the PV properties of the synthesized donors by fabricating BHJ solar cells with a typical structure of ITO/PEDOT:PSS/Donors: PC61BM/LiF/Al. Among them, CZ(TDPP)2 revealed a promising performance in PV devices with a power conversion efficiency (PCE) of 1.50%, along with an open-circuit voltage (VOC) of 0.66 V, a short-circuit current density (JSC) of 4.12 mA cm-2, and a fill factor (FF) of 0.44, under an illumination of AM 1.5G (80 mW cm-2).
- Zhang, Ling,Zeng, Shaohang,Yin, Lunxiang,Ji, Changyan,Li, Kechang,Li, Yanqin,Wang, Yue
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supporting information
p. 632 - 639
(2013/03/28)
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- SECONDARY HOLE TRANSPORTING LAYER WITH DIARYLAMINO-PHENYL-CARBAZOLE COMPOUNDS
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Novel diarylamino phenyl carbazole compounds are provided. By appropriately selecting the nature of the diarylamino substituent and the substitution on the carbazole nitrogen, compounds with appropriate HOMO and LUMO energies can be obtained for use as materials in a secondary hole transport layer.
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Paragraph 0126; 0127
(2013/09/26)
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- Synthesis and photovoltaic behaviors of benzothiadiazole- and triphenylamine-based alternating copolymers
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A series of donor-acceptor (D-A) alternating copolymers (P1, P2 and P3) with thiophene-benzothiadiazole-thiophene-triphenylamine main chain have been synthesized by Suzuki polycondensation. P1, P2, and P3 possess medium optical band gaps of 1.99, 1.97 and 1.93 eV, respectively. Bulk heterojunction polymer solar cells (BHJ PSCs) with these polymers as donor and PC71BM as acceptor showed power conversion efficiency (PCE) in the range of 2.1-2.8%. The highest PCE of 2.8 % was achieved for P1 with short circuit current (J sc) of 7.8 mA/cm2. This study offers a useful and important insight for designing triphenylamine derivative-based polymers used for efficient PSCs.
- Wang, Ming,Li, Cuihong,Lv, Aifeng,Wang, Zhaohui,Bo, Zhishan,Zhang, Fengling
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experimental part
p. 324 - 332
(2012/05/21)
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- Catalytic, atom-economical radical arylation of epoxides
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A slow electron waltz: Catalysis in single-electron steps with radicals as intermediates is essential for an atom-economical arylation of epoxides with a proton-coupled electron transfer as a key step. Stabilization of the catalyst is essential for low catalyst loading, as demonstrated by reaction-progress kinetic analysis, cyclic voltammetry, and calculations. Copyright
- Gansaeuer, Andreas,Behlendorf, Maike,Von Laufenberg, Daniel,Fleckhaus, Andre,Kube, Christian,Sadasivam, Dhandapani V.,Flowers II, Robert A.
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supporting information; experimental part
p. 4739 - 4742
(2012/06/30)
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- Cathodic reduction of diazonium salts in aprotic medium
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Cathodic reduction of diazonium salts in acetonitrile led to the formation of azobenzenes, in good to moderate yields, and diarylamines as minoritary products. The reactions were carried out at the second reduction potential of the diazonium salts, involving aryl anions in the formation of the products.
- Barba, Fructuoso,Batanero, Belen,Tissaoui, Khalil,Raouafi, Noureddine,Boujlel, Khaled
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experimental part
p. 973 - 976
(2011/11/05)
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- Preparation and characterization of N-Anisyl-substituted Hexaaza[1 6]paracyclophane
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Localized or delocalized? For the first time, a cyclic oligoaniline, hexaaza[16]paracyclophane, has been prepared (see picture; carbon: gray; nitrogen: blue; hydrogen: light gray). The macrocycle exhibits a high electron-donating ability, and furthermore, the spin of the corresponding radical cation was delocalized over the macrocyclic molecular backbone.
- Ito, Akihiro,Yokoyama, Yuichiro,Aihara, Ryosuke,Fukui, Koji,Eguchi, Shoko,Shizu, Katsuyuki,Sato, Tohru,Tanaka, Kazuyoshi
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experimental part
p. 8205 - 8208
(2011/02/23)
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- OLIGOANILINE COMPOUND
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Any of the oligoaniline compounds with a triphenylamine structure represented by the formula (1) exhibits satisfactory light emitting efficiency and brightness performance when used in either an OLED device or a PLED device and is further satisfactory in the solubility in organic solvents so as to be applicable to various coating methods. (each of R1 and R2 independently is a hydrogen atom, an optionally substituted monovalent hydrocarbon group, t-butoxycarbonyl, etc.; each of R3 to R34 independently is a hydrogen atom, hydroxyl, silanol, thiol, carboxyl, a phosphoric group, a phosphoric ester group, ester, thioester, amido, nitro, an optionally substituted monovalent hydrocarbon group, etc.; and each of m and n is an integer of 1 or greater provided that they satisfy the relationship m+n ≤ 20).
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Page/Page column 46-47
(2010/01/29)
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- Novel aspects of a convenient synthesis and of electroproperties of derivatives based on diphenylamine
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The substituted monomers 4a,c,d, 5a,b, 6a, 7a,b, and 8a of novel poly(diphenylamines), possessing the respective photochromic groups, were synthesized by the Stille cross-coupling methodology (Scheme). The hyperbranched structures were characterized by 1H- and 13C-NMR spectroscopy. The obtained monomers show good stability in common organic solvents such as CHCl3, toluene, and CH2Cl2, and exhibit excellent thermal stability. Electrochemical results and theoretical calculations suggest that oxidation and reduction of the monomers start from the side of the amine function and the five-membered heterocyclic ring moieties, respectively.
- Idzik, Krzysztof,Soloducho, Jadwiga,Cabaj, Joanna,Mosiadz, Mariusz,Lapkowski, Mieczyslaw,Golba, Sylwia
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body text
p. 618 - 627
(2009/02/07)
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- N,N-di(4-halophenyl)nitrenium ions: Nucleophilic trapping, aromatic substitution, and hydrogen atom transfer
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(Figure Presented) The reactive intermediates N,N-di(4-chlorophenyl) nitrenium ion and N,N-di(4-bromophenyl)nitrenium ion were generated through photolysis of the corresponding N-amino(2,4,6,-collidinium) ions. The behavior of these diarylnitrenium ions was characterized by laser flash photolysis, analysis of the stable photoproducts, and ab initio calculations with density functional theory. The latter predict these species to have singlet ground states. The halogenated diarylnitrenium ions are significantly longer lived than the unsubstituted diphenylnitrenium ion. Specifically, cyclization to form carbazole derivatives occurs negligibly, if at all, with the halogenated derivatives. They do, however, carry out most of the characteristic reactions of singlet arylnitrenium ions, including combining with nucleophiles on the aryl rings, adding to arenes, and accepting electrons from readily oxidized traps. Interestingly these species also abstract H atoms from 1,4-cyclohexadiene and various phenol derivatives. The implication of the latter process in relation to the computed singlet-triplet energy gaps of ca. -12.5 kcal/mol is discussed.
- Thomas, Selina I.,Falvey, Daniel E.
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p. 4626 - 4634
(2008/02/07)
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- Pyrazine derivative, and light emitting element, display device, electronic device using the pyrazine derivative
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It is an object to provide a novel material having a bipolar property, a light emitting element provided with the novel material, and a display device that includes the light emitting element. It is an object to provide a pyrazine derivative represented by the following general formula (g-1).
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- Quinoxaline derivative, and light emitting element, light emitting device, and electronic appliance using the same
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A quinoxaline derivative expressed by the general formula (1) is provided. (Each of R1 to R12 represents one of a hydrogen atom, a halogen atom, an alkyl group, an alkoxyl group, an acyl group, a dialkyl amino group, a diarylamino group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocycle group. Ar1 represents one of a substituted or unsubstituted biphenyl group and a substituted or unsubstituted terphenyl group, and Ar2 represents one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, and a substituted or unsubstituted monocyclic heterocycle group.)
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- Two-photon fluorescent holographic rewritable micropatterning
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Monomeric amorphous systems involving an upper azo-based layer and a lower fluorophore layer have been carefully designed to enable holographic formation of micrometric emissive photopatterns through reversible photoinduced mass migration of azoderivatives. The fluorescent patterns evidenced by NIR biphotonic excitation match the micrometric surface relief. After successful erasure by using a circularly polarized visible light, new patterns can be written again. Copyright
- Ishow, Elena,Brosseau, Arnaud,Clavier, Gilles,Nakatani, Keitaro,Pansu, Robert B.,Vachon, Jean-Jacques,Tauc, Patrick,Chauvat, Dominique,Mendonca, Cleber R.,Piovesan, Erick
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p. 8970 - 8971
(2008/02/09)
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- A convenient and selective method for the para-bromination of aromatic compounds with potassium bromide in the presence of poly(4-vinylpyridine)- supported peroxodisulfate in nonaqueous solution
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A convenient and selective procedure for the para-bromination of aromatic compounds has been developed using potassium bromide in the presence of poly(4-vinylpyridine)-supported peroxodisulfate in nonaqueous solution.
- Tajik,Mohammadpoor-Baltork,Hassan-Zadeh,Rafiee Rashtabadi
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p. 1282 - 1284
(2008/03/27)
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- New luminescent compositions and their uses
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High quantum yield luminescent monomers, oligomers, and polymers, comprising benzotriazole repeating units and derivatives thereof have been discovered and utilized in optical devices and components therefor, including electroluminescent devices, light emitting devices, photoluminescent devices, organic light emitting diodes (OLEDs), OLED displays, sensors, and the like.
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- Bromination of aromatic compounds with potassium bromide in the presence of poly(4-vinylpyridine)-supported bromate in nonaqueous solution
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A simple, efficient, and mild method for selective bromination of activated aromatic compounds using potassium bromide in the presence of poly(4-vinylpyridine)-supported bromate in nonaqueous solution is reported. The results obtained revealed excellent to good selectiveity between ortho and para positions of methoxyarenes, anilines, and phenols. Copyright Taylor & Francis, Inc.
- Tajik, Hassan,Shirini, Farhad,Hassan-Zadeh, Parwin,Rashtabadi, Hassan Rafiee
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p. 1947 - 1952
(2007/10/03)
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- Photochemical generation of nitrenium ions from protonated 1,1-diarylhydrazines
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(Chemical Equation Presented) Laser flash photolysis experiments, chemical trapping studies, and time-dependent density functional theory calculations demonstrate that photolysis of protonated 1,1-diarylhydrazines generates N,N-diarylnitrenium ions.
- Winter, Arthur H.,Thomas, Selina I.,Kung, Andrew C.,Falvey, Daniel E.
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p. 4671 - 4674
(2007/10/03)
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- Reactivity of tris(trimethylsilyl)silane toward diarylaminyl radicals
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Absolute rate constants for the reaction of tri-tert-butylphenoxyl radical (ArO·) with (TMS)3SiH were measured spectrophotometrically in the temperature range 321-383 K. Rate constants for the hydrogen abstraction from (TMS)3SiH by diarylaminyl radicals of type (4-X-C6H4)2N· were determined by using a method in which the corresponding amines catalyze the reaction of ArO· with (TMS)3SiH. At 364.2 K, rate constants·are in the range of 2-50 M-1 s-1 for X = H, CH3, CH3O, and Br, whereas the corresponding value for ArO· is 3 orders of magnitude lower. A common feature of these reactions is the low preexponential factor [log(A/M-1 s-1) of 4.4 and 5.2 for ArO· and Ph2N·, respectively], which reflects high steric demand in the transition state. A semiempirical approach based on intersecting parabolas suggests that the observed reactivity is mainly related to the enthalpy of the reaction and allowed to estimate activation energies for the reaction of (4-X-C6H4)2N· and ArO· radicals with a variety of silicon hydrides.
- Varlamov,Denisov,Chatgilialoglu
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p. 6317 - 6322
(2007/10/03)
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- Multi-armed chromophores with very large two-photon absorption cross-sections
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Provided are chromophores with very large two-photon absorption cross-sections. One group of these chromophores has the formula: (T—Q)n—N—Phm wherein Q is a single bond or 1,4-phenylene, Ph is a phenyl group, n has a value of 1-3 and m has a value of 3?n, and wherein T is wherein R1and R2are alkyl groups having 1 to 20 carbon atoms, provided that when Q is a single bond, the value of n is 2 or 3. Another group of these chromophores has the formula: (T—Q)n—G—Phm wherein T is as defined above, Q is a single bond or 1,4-phenylene, Ph is a phenyl group, n has a value of 1-4 and m has a value of 4?n, and wherein G is a 4-arm core unit. Yet another group of these chromophores has the formula: (T—Q)n—G—Phm wherein T is as described previously, Q is a single bond or 1,4-phenylene, Ph is a phenyl group, n has a value of 1-6 and m has a value of 6?n, and wherein G is a 6-arm core unit.
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- An improved synthesis of camphorquinone-3-oxime
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Camphorquinone 3-oxime is prepared in 77% yield in one step from camphor. The synthesis avoids the use of toxic selenium reagents, and provides the syn compound as the major stereoisomer.
- Love, Brian E.,Jones, Edward G.
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p. 2831 - 2840
(2007/10/03)
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- KINETICS OF THE REACTION OF THE 2,4,6-TRI-TERT-BUTYLPHENOXYL RADICAL WITH AROMATIC AMINES UNDER QUASIEQUILIBRIUM CONDITIONS, AND THE DISSOCIATION ENERGY OF THE N-H BOND IN AROMATIC AMINES
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We have studied the kinetics of the reaction of the 2,4,6-tri-tert butylphenoxyl radical with 11 aromatic amines under quasiequilibrium conditions.The equilibrium constant for each amine was determined from the kinetic results.These values, together with their temperature dependence, were used to calculate the dissociation energy of the N-H bond in the 11 aromatic amines.By using earlier results for the reaction of the aroxyl radical with cumyl hydroperoxide, catalyzed by aromatic amines, we have calculated the rate constants for the reaction of 10 aminyl radicals with cumyl hydroperoxide and of cumylperoxy radicals with 10 aromatic amines.
- Varlamov, V. T.,Denisov, E. T.
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p. 657 - 662
(2007/10/02)
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- Bromation regioselective en serie aromatique. I: Monobromation en position para de phenols et d'amines aromatiques par le tribromure de tetrabutylammonium
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The reaction of tetrabutylammonium tribromide (TBABr3) with phenols and aromatic amines in aprotic and non-basic solvents at 20 deg C gives exclusively the corresponding para-brominated compounds in high yields.A mechanism involving electrophilic substitution by the tribromide anion Br3- itself is suggested to account for the results, especially the regioselective para bromination.Key words: bromination, tetrabutylammonium tribromide, phenols, aromatic amines.
- Berthelot, Jacques,Guette, Catherine,Desbene, Paul-Louis,Basselier, Jean-Jacques,Chaquin, Patrick,Masure, Daniel
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p. 2061 - 2066
(2007/10/02)
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- Condensations of 1,4-Cyclohexanediones and Secondary Aromatic Amines. II. N-Phenylation of Diarylamines
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The condensations of 1,4-cyclohexanedione with several diphenylamines were investigated in order to determine the limit of the utility of this reaction for the N-phenylation of aromatic secondary amines. 4-Methoxy-, 4,4'-dimethyl-, and 4,4'-dibromodiphenylamines produced their N-phenylated compounds in fairly good yields, but 4-hydroxy-, 3-methoxy-, and 4,4'-bis(dimethylamino)diphenylamines produced poor yields.Nitro-substituted diphenylamines gave N-phenyl derivatives in low yields along with N-4-hydroxyphenyl derivatives.N,N'-Diphenyl-p-phenylenediamine and N,N'-diphenylbenzidine gave correspondig tetra-N-phenyl diamines in good yields.The condensation of N-phenyl-1-naphthylamine, N-phenyl-2-naphthylamine, di-2-pyridylamine, phenothiazine, and carbazole with 1,4-cyclohexanedione were also examined.
- Haga, Kazuo,Iwaya, Katsumasa,Kaneko, Ryohei
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p. 803 - 808
(2007/10/02)
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- REGIOSELECTIVE MONOBROMINATION OF AROMATIC AMINES WITH TETRABUTYLAMMONIUM TRIBROMIDE
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A simple and efficient method for monobromination of aromatic amines predominantly in the para position is reported.Tetrabutylammonium tribromide is used at 20 deg C and yields of parabromoanilines are higher than 90percent.
- Berthelot, J.,Guette, C.,Essayegh, M.,Desbene, P.L.,Basselier, J.J.
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p. 1641 - 1646
(2007/10/02)
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