- Pd-Catalyzed Dearomative Three-Component Reaction of Bromoarenes with Diazo Compounds and Allylborates
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A catalytic dearomative three-component reaction of bromoarenes with TMS-diazomethane and allyl borate was developed. The key of this assembling reaction is the use of a diazo compound to generate a Pd-π-benzyl intermediate through a Pd-carbene species. T
- Komatsuda, Masaaki,Kato, Hiroki,Muto, Kei,Yamaguchi, Junichiro
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- Synthesis and properties of chromophore-functionalized monovinylsilsesquioxane derivatives
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A facile and efficient Pd-based Suzuki-Miyaura coupling reaction leading to mixed chromophores with styryl fragments, enabling their further application, is presented. We also disclose their use in the formation of monofunctionalized silsesquioxanes with a chromophore group covalently bound to a T8 core that have been prepared via a cross-metathesis reaction. These new materials were studied in terms of their photophysical and also thermal properties.
- ?ak, Patrycja,Bo?t, Ma?gorzata,Dudziec, Beata,Grzelak, Magdalena,Januszewski, Rafa?,Marciniak, Bronislaw,Marciniec, Bogdan,Rachuta, Karolina
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- ORGANIC COMPOUND, PRODUCTION METHOD OF THE SAME, ORGANIC LIQUID CRYSTAL, ORGANIC SEMICONDUCTOR AND THE LIKE
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PROBLEM TO BE SOLVED: To provide an organic semiconductor showing high mobility and high thermal stability and having excellent solubility, an organic compound for the organic semiconductor, and a production method of the compound. SOLUTION: The present invention discloses an organic compound represented by the formula (1) and a production method of the compound, and applications of an organic semiconductor and the like using the organic compound. In the formula, Ar is an aromatic group selected from a phenyl or a thienyl which may have a substituent; one of R1 and R2 is a linear aliphatic group and the other is a hydrogen atom; and an acetylene bond in the parenthesis may be present or absent. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
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Paragraph 0140; 0142
(2020/07/25)
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- Decarboxylative Bromination of Heteroarenes: Initial Mechanistic Insights
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After an initial report from our laboratory describing metal-free decarboxylative halogenation of various azaheteroarenes, we set out to investigate the possible mechanism by which this chemistry occurs. Evidence from this mechanistic investigation sugges
- Patel, Pritesh R.,Henderson, Scott H.,Roe, Mark S.,Honey, Mark A.
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supporting information
p. 1603 - 1607
(2020/09/09)
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- A Rational Design of Highly Controlled Suzuki-Miyaura Catalyst-Transfer Polycondensation for Precision Synthesis of Polythiophenes and Their Block Copolymers: Marriage of Palladacycle Precatalysts with MIDA-Boronates
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Herein, we report a highly efficient Suzuki-Miyaura catalyst-transfer polycondensation (SCTP) of 3-alkylthiophenes using bench-stable but highly active Buchwald dialkylbiarylphospine Pd G3 precatalysts and N-methylimidodiacetic (MIDA)-boronate monomers. Initially, the feasibility of the catalyst-transfer process was examined by screening various dialkylbiarylphospine-Pd(0) species. After optimizing a small molecule model reaction, we identified both RuPhos and SPhos Pd G3 precatalysts as excellent catalyst systems for this purpose. On the basis of these model studies, SCTP was tested using either RuPhos or SPhos Pd G3 precatalyst, and 5-bromo-4-n-hexylthien-2-yl-pinacol-boronate. Poly(3-hexylthiophene) (P3HT) was produced with controlled molecular weight and narrow dispersity for a low degree of polymerization (DP) only, while attempts to synthesize P3HT having a higher DP with good control were unsuccessful. To improve the control, slowly hydrolyzed 5-bromo-4-n-hexylthien-2-yl-MIDA-boronate was introduced as a new monomer. As a result, P3HT and P3EHT (up to 17.6 kg/mol) were prepared with excellent control, narrow dispersity, and excellent yield (>90%). Detailed mechanistic investigation using 31P NMR and MALDI-TOF spectroscopy revealed that both fast initiation using Buchwald precatalysts and the suppression of protodeboronation due to the protected MIDA-boronate were crucial to achieve successful living polymerization of P3HT. In addition, a block copolymer of P3HT-b-P3EHT was prepared via SCTP by sequential addition of each MIDA-boronate monomer. Furthermore, the same block copolymer was synthesized by one-shot copolymerization for the first time by using fast propagating pinacol-boronate and slow propagating MIDA-boronate.
- Seo, Kyeong-Bae,Lee, In-Hwan,Lee, Jaeho,Choi, Inho,Choi, Tae-Lim
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p. 4335 - 4343
(2018/04/05)
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- Thiophene-S, S -dioxidized diarylethenes for light-starting irreversible thermosensors that can detect a rise in heat at low temperature
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Diarylethenes having trimethylsilyl and triethylsilyl groups at the reactive positions and their S,S-dioxidized diarylethenes were synthesized and their optical and thermal properties were investigated. Upon irradiation with ultraviolet light, the diarylethenes and thiophene-S,S-dioxidized diarylethenes underwent photochromic reactions from the colourless open-ring isomer to the coloured closed-ring isomer. The photogenerated closed-ring isomers were found to undergo thermal bleaching reactions to produce colourless byproducts. In particular, the thiophene-S,S-dioxidized diarylethene having a triethylsilyl group at the reactive positions underwent the thermal bleaching reaction even at -40 °C. Such materials could be used as light-starting irreversible thermosensors that can detect a rise in heat at low temperature.
- Kitagawa, Daichi,Tanaka, Koki,Kobatake, Seiya
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p. 6210 - 6215
(2017/07/11)
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- Thiophene-Alkyne-Based CMPs as Highly Selective Regulators for Oxidative Heck Reaction
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Thiophenes containing an adjacent C≡C group as ligands for PdII-promoted organic reactions are reported for the first time. These ligands were utilized as catalytic sites and integrated into the skeleton of conjugated microporous polymers. By e
- Li, Ren-Hao,Ding, Zong-Cang,Li, Cun-Yao,Chen, Jun-Jia,Zhou, Yun-Bing,An, Xiao-Ming,Ding, Yun-Jie,Zhan, Zhuang-Ping
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supporting information
p. 4432 - 4435
(2017/09/11)
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- Structural requirements for palladium catalyst transfer on a carbon-carbon double bond
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Intramolecular transfer of tBu3PPd(0) on a carbon-carbon double bond (C=C) was investigated by using Suzuki-Miyaura coupling reaction of dibromostilbenes with aryl boronic acid or boronic acid esters in the presence of various additi
- Nojima, Masataka,Ohta, Yoshihiro,Yokozawa, Tsutomu
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supporting information
p. 5682 - 5685
(2015/05/20)
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- Acid-base-responsive intense charge-transfer emission in donor-acceptor-conjugated fluorophores
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Herein we report on the synthesis and acid-responsive emission properties of donor-acceptor (D-A) molecules that contain a thienothiophene unit. 2-Arylthieno[3,2-b]thiophenes were conjugated with an N-methylbenzimidazole unit to form acid-responsive D-A-t
- Inouchi, Toshifumi,Nakashima, Takuya,Kawai, Tsuyoshi
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supporting information
p. 2542 - 2547
(2014/10/15)
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- Gold-catalyzed oxidative coupling of arylsilanes and arenes: Origin of selectivity and improved precatalyst
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The mechanism of gold-catalyzed coupling of arenes with aryltrimethylsilanes has been investigated, employing an improved precatalyst (thtAuBr3) to facilitate kinetic analysis. In combination with linear free-energy relationships, kinetic isotope effects, and stoichiometric experiments, the data support a mechanism involving an Au(I)/Au(III) redox cycle in which sequential electrophilic aromatic substitution of the arylsilane and the arene by Au(III) precedes product-forming reductive elimination and subsequent cycle-closing reoxidation of the metal. Despite the fundamental mechanistic similarities between the two auration events, high selectivity is observed for heterocoupling (C-Si then C-H auration) over homocoupling of either the arylsilane or the arene (C-Si then C-Si, or C-H then C-H auration); this chemoselectivity originates from differences in the product-determining elementary steps of each electrophilic substitution. The turnover-limiting step of the reaction involves associative substitution en route to an arene π-complex. The ramifications of this insight for implementation of the methodology are discussed.
- Ball, Liam T.,Lloyd-Jones, Guy C.,Russell, Christopher A.
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supporting information
p. 254 - 264
(2014/01/23)
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- AROMATIC AMINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT ELEMENT
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Provided are a long-lifetime organic electroluminescence device which can be fabricated in an improved yield owing to suppressed crystallization of molecules, and an aromatic amine derivative that realizes the device, i.e. , a novel aromatic amine derivative having a specific structure. Specifically provided are an organic electroluminescence device, including an organic thin film layer formed of one or more layers including at least a light emitting layer, the organic thin film layer being interposed between a cathode and an anode, and an aromatic amine derivative for at least one layer of the organic thin film layer, in particular, a hole transporting layer, the derivative having at least one such structure that a substituent in which two or more specific heterocycles are linked to each other, in particular, a substituent in which two or more specific heterocycles are linked through an aryl group is bonded to an amine through an aryl group.
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Page/Page column 27-28; 37
(2012/01/11)
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- NOVEL COMPOUND AND ORGANIC ELECTRONIC DEVICE USING SAME
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The present invention relates to a novel compound and an organic light emitting device using the compound, and the compound according to the present invention may largely improve a life span, efficiency, electrochemical stability and thermal stability of the organic light emitting device.
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Page/Page column 43
(2011/08/03)
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- AROMATIC AMINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
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Provided are an organic electroluminescent device including an aromatic amine derivative formed of a specific structure having a thiophene structure and an organic thin film layer interposed between a cathode and an anode and formed of one layer or a plurality of layers including at least a light emitting layer, in which at least one layer of the organic thin film contains the aromatic amine derivative alone or as a component of a mixture, the organic electroluminescent device in which molecules hardly crystallize, and which decreases a driving voltage, can be produced with improved yields upon the production of the organic electroluminescent device, and has a long lifetime, and an aromatic amine derivative realizing the organic electroluminescent device.
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Page/Page column 46
(2010/05/13)
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- The irreversible thermo-bleaching function of a photochromic diarylethene having trimethylsilyl groups
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A new function of a photochromic diarylethene, having trimethylsilyl groups at the reactive positions, has been developed. Upon alternating ultraviolet and visible light irradiation, the diarylethene showed photoreversible photochromism in a polymer film, as well as in solution. The colored state changed to colorless immediately upon heating at 100 °C. The colorless state, which is different from the open-ring isomer, was stable under both ultraviolet and visible light irradiation. Such photochromic materials could potentially be used in applications as secret display materials. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2009.
- Kobatake, Seiya,Imagawa, Hiroyuki,Nakatani, Hidenori,Nakashima, Seiichiro
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scheme or table
p. 1362 - 1367
(2009/09/24)
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- Organic compounds for electroluminescence and organic electroluminescent devices using the same
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Disclosed is a novel group of compounds having a general structure of anthracene body substituted with at least one thiophenyl group, which can be further substituted with various substituent groups. These new compounds are generally compatible with organic electroluminescence. Also disclosed are organic electroluminescent devices and method of making the same. The organic electroluminescent devices include at least one of the compounds in various layers thereof. Organic electroluminescent devices employing the new compounds in their light-emitting layers show outstanding stability.
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Page/Page column 77
(2009/02/11)
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- Brominated thiophenes as precursors in the preparation of brominated and arylated anthraquinones
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Brominated anthraquinones can be synthesized directly from bromothiophenes when these are reacted with 1,4-naphthoquinones in the presence of meta-chloroperoxybenzoic acid. The bromoanthraquinones are versatile building blocks in the preparation of arylated anthraquinones and of extended π-systems with interspersed anthraquinone units.
- Thiemann, Thies,Tanaka, Yasuko,Iniesta, Jesus
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experimental part
p. 1013 - 1031
(2009/10/10)
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- ORGANIC METAL COMPLEXES DERIVATIVE AND ORGANIC LIGHT EMITTING DEVICES USING THE SAME
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The present invention relates to a novel organic metal complex derivative and to an organic light emitting device comprising the same.
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Page/Page column 30-31
(2009/01/24)
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- AROMATIC AMINE DERIVATIVES AND ORGANIC ELECTROLUMINESCENT DEVICE USING SAME
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The present invention provides a novel aromatic amine derivative having a specific structure and an organic electroluminescence device in which an organic thin film layer comprising a single layer or plural layers including at least a light emitting layer is interposed between a cathode and an anode, wherein at least one layer in the above organic thin film layer, particularly a hole injecting layer contains the aromatic amine derivative described above in the form of a single component or a mixed component. Use of the aromatic amine derivative described above materialize an organic electroluminescence device which reduces an operating voltage and makes molecules less liable to be crystallized and which enhances a yield in producing the organic EL device and has a long lifetime.
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Page/Page column 51
(2008/12/04)
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- General facile synthesis of 2,5-diarylheteropentalenes
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Palladium-catalyzed cross-coupling reactions of various heteropentalene derivatives were systematically studied. A general three-step synthesis of 2,5-diarylheteropentalenes involving two Suzuki or Negishi couplings and a regiospecific bromination was developed. Nonsymmetrical 2,5-diaryl-furans, thiophenes, pyrroles, 1,3-thiazoles, 1,3-oxazoles, 1,3,4-thiadiazoles, and 1,3,4-oxadiazoles were prepared in 31-67% isolated yield (three steps).
- Vachal, Petr,Toth, Leslie M.
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p. 7157 - 7161
(2007/10/03)
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- NEW ORGANIC COMPOUNDS FOR ELECTROLUMINESCENCE AND ORGANIC ELECTROLUMINESCENT DEVICES USING THE SAME
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Disclosed is a novel group of compounds having a general structure of anthracene body substituted with at least one thiophenyl group, which can be further substituted with various substituent groups. These new compounds are generally compatible with organic electroluminescence. Also disclosed are organic electroluminescent devices and method of making the same. The organic electroluminescent devices include at least one of the compounds in various layers thereof. Organic electroluminescent devices employing the new compounds in their light-emitting layers show outstanding stability.
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Page/Page column 73
(2010/02/07)
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- Molecular compound, luminous material using the same, and luminous element
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Provided is a new molecular compound excellent in luminous property, which has a molecular structure wherein a thiophene ring and a benzene (or naphthalene) ring are directly bonded to each other, as a molecular compound making it possible to control its
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- Synthesis of thiophene/phenylene co-oligomers. I. Phenyl-capped oligothiophenes
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We report the synthesis of phenyl-capped oligothiophenes via improved synthetic schemes. These schemes are based on the Grignard coupling reaction and enable us to obtain the target compounds at high yields. The resulting materials have been fully charact
- Hotta,Lee,Tamaki
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- The preparations and some properties of mixed aryl-thienyl oligomers and polymers
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The syntheses by transition metal coupling reactions of a large number of oligomers constructed from benzene and thiophene rings are described. The first use of arylcadmium chlorides for such coupling reactions is reported. The routes chosen allow for rational variation in the modes of linkage, the substitution and the proportions of the two units. The benzene and thiophene rings are always joined in a known order and may bear a wide variety of regularly spaced functional groups. Additionally the shape of the oligomers may be varied at will. In all cases p-type doping with iodine or ferric chloride leads to large enhancements in conductivity.
- Pelter, Andrew,Jenkins, Ieuan,Jones, D. Elfyn
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p. 10357 - 10400
(2007/10/03)
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