- Thieno[2,3-b]indole-Based Small Push-Pull Chromophores: Synthesis, Structure, and Electronic Properties
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Small push-pull molecules were synthesized in high yields by connecting a N-methyl or N-phenyl substituted thieno[2,3-b]indole electron-donating block directly to a 2,2-dicyanovinyl or (1-(dicyanomethylene)-3-oxo-1-inden-2-ylidene)methyl electron-withdraw
- Baert, Fran?ois,Cabanetos, Clément,Allain, Magali,Silvestre, Virginie,Leriche, Philippe,Blanchard, Philippe
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Read Online
- Mo–Catalyzed One-Pot Synthesis of N-Polyheterocycles from Nitroarenes and Glycols with Recycling of the Waste Reduction Byproduct. Substituent-Tuned Photophysical Properties
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A catalytic domino reduction–imine formation–intramolecular cyclization–oxidation for the general synthesis of a wide variety of biologically relevant N-polyheterocycles, such as quinoxaline- and quinoline-fused derivatives, and phenanthridines, is reported. A simple, easily available, and environmentally friendly dioxomolybdenum(VI) complex has proven to be a highly efficient and versatile catalyst for transforming a broad range of starting nitroarenes involving several redox processes. Not only is this a sustainable, step-economical as well as air- and moisture-tolerant method, but also it is worth highlighting that the waste byproduct generated in the first step of the sequence is recycled and incorporated in the final target molecule, improving the overall synthetic efficiency. Moreover, selected indoloquinoxalines have been photophysically characterized in cyclohexane and toluene with exceptional fluorescence quantum yields above 0.7 for the alkyl derivatives.
- Hernández-Ruiz, Raquel,Rubio-Presa, Rubén,Suárez-Pantiga, Samuel,Pedrosa, María R.,Fernández-Rodríguez, Manuel A.,Tapia, M. José,Sanz, Roberto
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supporting information
p. 13613 - 13623
(2021/08/23)
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- COMPOUND AND PHOTOELECTRIC DEVICE, IMAGE SENSOR AND ELECTRONIC DEVICE INCLUDING THE SAME
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A compound of Chemical Formula 1, and an organic photoelectric device, an image sensor, and an electronic device including the same are disclosed: In Chemical Formula 1, each substituent is the same as defined in the detailed description.
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Paragraph 0357-0359
(2021/01/29)
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- Compound taking quinolinone derivative as core and application of compound in organic electroluminescent device
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The invention discloses a compound taking a quinolinone derivative as a core and an application of the compound in an organic electroluminescent device. The compound structurally contains the quinolinone derivative as an electron acceptor, so that transmi
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Paragraph 0093-0095
(2020/04/17)
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- TRICYCLIC CRBN LIGANDS AND USES THEREOF
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The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of CRBN, and the treatment of CRBN-mediated disorders.
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Paragraph 0764; 0765
(2020/01/24)
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- IRIDIUM COMPLEX AND ORGANIC ELECTROLUMINESCENCE DEVICE USING THE SAME
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The present invention discloses an iridium complex of formula (1) and an organic electroluminescence device employing the iridium complex as the phosphorescent dopant material. The organic EL device can display good performance, such as lower driving volt
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Paragraph 0021; 0022
(2019/04/18)
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- ORGANIC COMPOUND, ORGANIC ELECTRONIC DEVICE HAVING THE SAME, PHOTOELECTRIC CONVERSION ELEMENT HAVING THE SAME, IMAGING ELEMENT AND IMAGING DEVICE
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PROBLEM TO BE SOLVED: To provide an organic compound having a high glass transition temperature, and an organic electronic device having the same. SOLUTION: The present invention provides an organic compound represented by formula [1] (R1-R10 independently represent H, halogen, cyano, alkyl, aryl, or heteroaryl; n is an integer of 0-2; m is an integer of 2-4; A is fluorene ring, benzofluorene ring, dibenzofluorene ring or spirofluorene ring; and B is C6-12 aryl or C4-11 heteroaryl). SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2019,JPOandINPIT
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Paragraph 0162; 0163
(2019/04/04)
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- HETEROCYCLIC COMPOUND AND ORGANIC ELECTRONIC DEVICE COMPRISING THE SAME
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The present specification relates to a heterocyclic compound represented by chemical formula 1 and an organic electronic device comprising the heterocyclic compound in an organic active layer. When the heterocyclic compound is used in the organic active l
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Paragraph 0186-0189; 0202
(2019/12/31)
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- Delay fluorescent compound and organic electroluminescence device employing same
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The invention discloses a compound used as organic electroluminescence material. The compound has a structure indicated in formula (1) and the compound has good performance when serving as the delay fluorescent material of a light emitting layer or organi
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Paragraph 0061; 0062; 0063
(2018/04/03)
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- Metal-free deoxygenation and reductive disilylation of nitroarenes by organosilicon reducing reagents
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A metal-free deoxygenation and reductive disilylation of nitroarenes was achieved using N,N’-bis(trime-thylsilyl)-4,4’-bipyridinylidene (1) under mild and neutral reaction conditions, and a broad functional group tolerance was possible in this reaction. Mono-deoxygenation, giving a synthetically valuable N,O-bis(trimethylsilyl)phe-nylhydroxylamine (7a) as a readily available and safe phenylnitrene source from nitrobenzene, and double-deoxy-genation, giving N,N-bis(trimethylsilyl)anilines 8, were easily controlled by varying the amounts of 1 and reaction temperature as well as adding dibenzothiophene (DBTP). Reaction of 2-arylnitrobenzenes with 1 resulted in the formation of the corresponding carbazoles 14 via in situ-gen-erated phenylnitrene species derived by thermolysis of N,O-bis(trimethylsilyl)phenylhydroxylamines 7, followed by their subsequent intramolecular C H insertion. In addition, the intramolecular N N coupling reaction proceeded in the reduction of 2,2’-dinitrobiphenyl derivatives by 1, giving the corresponding benzo[c]cinnolines.
- Bhattacharjee, Argha,Hosoya, Hiromu,Ikeda, Hideaki,Nishi, Kohei,Tsurugi, Hayato,Mashima, Kazushi
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supporting information
p. 11278 - 11282
(2018/10/20)
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- Polyaniline-Induced Arylation with Arenediazonium Salts Derived from Anilines
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A catalytic amount of a reduced form of polyaniline (a redox-active π-conjugated polymer) was found to induce C?H direct arylation of (hetero)arenes with arenediazonium salts prepared from anilines with methanesulfonic acid (MeSO3H) and tert-butyl nitrite (tBuONO). The difficult part of this method is the coexistence of an oxidant and a reductant in this sequential diazotization and arylation system; diazotization requires weak oxidants such as alkyl nitrites, whereas the arylation is induced by a reductant. This was achieved by the careful control of the amount of tBuONO (1.0 equivalent) for the diazotization step, and sequential arylation using 5 mol % of the polyaniline. The reaction took place under mild conditions without any metals or strong bases at room temperature, and the amino group is a formal leaving group. The scope of the substrates demonstrates the versatility in the combination of anilines with a variety of functional groups and several (hetero)arenes. Two-directional arylation for the synthesis of an unsymmetrical 1,4-diarylated (furyl and pyrrolyl groups) benzene was achieved, using mono-Boc-protected 1,4-phenylenediamine as a substrate. This shows potential for the synthesis of more complicated oligoarene compounds.
- Hata, Dai,Moriuchi, Toshiyuki,Hirao, Toshikazu,Amaya, Toru
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supporting information
p. 7703 - 7709
(2017/06/06)
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- Synthesis of heteroaryl compounds through cross-coupling reaction of aryl bromides or benzyl halides with thienyl and pyridyl aluminum reagents
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An efficient method for synthesis of useful biaryl building blocks containing 2-thienyl, 3-thienyl, 2-pyridyl, and 3-pyridyl moieties was provided through cross-coupling reactions of aryl bromides or benzyl halides with heteroaryl aluminum reagents in the presence of Pd(OAc)2 and (o-tolyl)3P. The coupling reaction also worked efficiently with heteroaryl bromides affording series of heterobiaryl compounds. The reaction of phenylbromide with in situ prepared 3-pyridyl aluminum was demonstrated to afford the product 8a in high yield. Additionally, the catalytic system was also suited well for the coupling reaction of benzyl halides with pyridyl aluminum reagents to afford series of pyridyl-arylmethane.
- Chen, Xu,Zhou, Lingmin,Li, Yimei,Xie, Tao,Zhou, Shuangliu
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p. 230 - 239
(2014/01/17)
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- Rapid synthesis of fused N-heterocycles by transition-metal-free electrophilic amination of arene C-H bonds
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We disclose an efficient and operationally simple protocol for the preparation of fused N-heterocycles starting from readily available 2-nitrobiaryls and PhMgBr under mild conditions. More than two dozen N-heterocycles, including two bioactive natural products, have been synthesized using this method. A stepwise electrophilic aromatic cyclization mechanism was proposed by DFT calculations. Controlled fusion: A transition-metal-free, low-temperature, and regioselective intramolecular amination of aromatic C(sp2)-H bonds provides fused N-heterocycles. This reaction is operationally simple and scalable (1-10 mmol) and the scope of substrates is wide (see scheme). Density functional calculations indicate that a stepwise electrophilic aromatic cyclization mechanism may be operative.
- Gao, Hongyin,Xu, Qing-Long,Yousufuddin, Muhammed,Ess, Daniel H.,Kuerti, Laszlo
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supporting information
p. 2701 - 2705
(2014/03/21)
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- NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
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Provided are novel organic electroluminescent compounds and an organic electroluminescent device using the same. Since the organic electroluminescent compound exhibits good luminous efficiency and excellent life property compared to the existing host material, it may be used to manufacture OLED devices having very superior operation life and consuming less power due to improved power efficiency.
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Page/Page column 13
(2011/09/15)
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- Design, synthesis, and fungicidal activity of novel analogues of pyrrolnitrin
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A series of novel analogues of pyrrolnitrin containing a thiophene moiety were designed and synthesized by a facile method, and their structures were characterized by 1H nuclear magnetic resonance (NMR) and high-resolution mass spectrometry. The isomers IV-h and V-h were isolated, and their structures were identified by 2D NMR, including heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC), and nuclear Overhauser effect spectrometry (NOESY) spectra. Their fungicidal activities against five fungi were evaluated, and the results indicated that some of the title compounds showed excellent fungicidal activities in vitro against Alternaria solani, Gibberella zeae, Physalospora piricola, Fusarium omysporum, and Cercospora arachidicola at the dosage of 50 μg mL-1. Some compounds shown moderate activity at low dosage. Compound V-h could be considered as a leading structure for further design of agricultural fungicides.
- Wang, Ming-Zhong,Xu, Han,Feng, Qi,Wang, L.I.-Zhong,Wang, S.U.-Hua,Li, Zheng-Ming
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experimental part
p. 7912 - 7918
(2010/09/03)
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- Microwave-enhanced cadogan cyclization: An easy access to the 2-substituted carbazoles and other fused heterocyclic systems
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A microwave-enhanced Suzuki-Miyaura cross-coupling reaction in combination with a microwave-assisted Cadogan reductive cyclization is presented as an easy access to a variety of 2-substituted carbazoles and other fused heterocyclic systems. Microwave irradiation was found very useful in minimizing the proto-deboronation issues in the cross-coupling reaction, and enhances the rate of reductive cyclization in a dramatic manner.
- Appukkuttan, Prasad,Van Der Eycken, Erik,Dehaen, Wim
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p. 127 - 133
(2007/10/03)
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- INTRAMOLECULAR DIAZO COUPLING OF 2-AMINOPHENYLTHIOPHENES. THE FORMATION OF ISOMERIC THIENOCINNOLINES
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Thieno- (4) and thieno-cinnolines (7) have been obtained by diazotisation and internal coupling of the corresponding 2-(o-aminophenyl)thiophenes.By the same reaction 3-(o-aminophenyl)-2,5-dimethylthiophene gives 1,3-dimethylthienolcinnoline (9).
- Barton, John W.,Lapham, David J.,Rowe, David J.
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p. 131 - 134
(2007/10/02)
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