- Modular and Selective Arylation of Aryl Germanes (C?GeEt3) over C?Bpin, C?SiR3 and Halogens Enabled by Light-Activated Gold Catalysis
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Selective C (Formula presented.) –C (Formula presented.) couplings are powerful strategies for the rapid and programmable construction of bi- or multiaryls. To this end, the next frontier of synthetic modularity will likely arise from harnessing the coupling space that is orthogonal to the powerful Pd-catalyzed coupling regime. This report details the realization of this concept and presents the fully selective arylation of aryl germanes (which are inert under Pd0/PdII catalysis) in the presence of the valuable functionalities C?BPin, C?SiMe3, C?I, C?Br, C?Cl, which in turn offer versatile opportunities for diversification. The protocol makes use of visible light activation combined with gold catalysis, which facilitates the selective coupling of C?Ge with aryl diazonium salts. Contrary to previous light-/gold-catalyzed couplings of Ar–N2+, which were specialized in Ar–N2+ scope, we present conditions to efficiently couple electron-rich, electron-poor, heterocyclic and sterically hindered aryl diazonium salts. Our computational data suggest that while electron-poor Ar–N2+ salts are readily activated by gold under blue-light irradiation, there is a competing dissociative deactivation pathway for excited electron-rich Ar–N2+, which requires an alternative photo-redox approach to enable productive couplings.
- Dahiya, Amit,Fricke, Christoph,Funes-Ardoiz, Ignacio,Gevondian, Avetik G.,Schoenebeck, Franziska,Sherborne, Grant J.
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Read Online
- Energy Gap between the Poly-p-phenylene Bridge and Donor Groups Controls the Hole Delocalization in Donor-Bridge-Donor Wires
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Poly-p-phenylene wires are critically important as charge-transfer materials in photovoltaics. A comparative analysis of a series of poly-p-phenylene (RPPn) wires, capped with isoalkyl (iAPPn), alkoxy (ROPPn), and dialkylamino (R2NPPn) groups, shows unexpected evolution of oxidation potentials, i.e., decrease (-260 mV) for iAPPn, while increase for ROPPn (+100 mV) and R2NPPn (+350 mV) with increasing number of p-phenylenes. Moreover, redox/optical properties and DFT calculations of R2NPPn/R2NPPn+? further show that the symmetric bell-shaped hole distribution distorts and shifts toward one end of the molecule with only 4 p-phenylenes in R2NPPn+?, while shifting of the hole occurs with 6 and 8 p-phenylenes in ROPPn+? and iAPPn+?, respectively. Availability of accurate experimental data on highly electron-rich dialkylamino-capped R2NPPn together with ROPPn and iAPPn allowed us to demonstrate, using our recently developed Marcus-based multistate model (MSM), that an increase of oxidation potentials in R2NPPn arises due to an interplay between the electronic coupling (Hab) and energy difference between the end-capped groups and bridging phenylenes (Δ?). A comparison of the three series of RPPn with varied Δ? further demonstrates that decrease/increase/no change in oxidation energies of RPPn can be predicted based on the energy gap Δ? and coupling Hab, i.e., decrease if Δ? ab (i.e., iAPPn), increase if Δ? > Hab (i.e., R2NPPn), and minimal change if Δ? ≈ Hab (i.e., ROPPn). MSM also reproduces the switching of the nature of electronic transition in higher homologues of R2NPPn+? (n ≥ 4). These findings will aid in the development of improved models for charge-transfer dynamics in donor-bridge-acceptor systems.
- Wang, Denan,Talipov, Marat R.,Ivanov, Maxim V.,Rathore, Rajendra
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Read Online
- Palladium-Catalyzed Enantioselective C(sp3)-H Arylation of 2-Propyl Azaaryls Enabled by an Amino Acid Ligand
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A palladium(II)-catalyzed enantioselective arylation of unbiased secondary C(sp3)-H bonds was developed. The enantioselectivity was controlled by the combination of a pyridyl or isoquinolinyl directing group and an amino acid, N-Boc-2-pentyl proline. A variety of 2-propyl azaaryls and biaryl iodides were employed to provide arylated products in moderate to good yields (up to 82%) with high enantioselectivities (up to 93:7 er). This reaction is a rare example of an amino-acid-enabled enantioselective acyclic methylene C(sp3)-H arylation. Furthermore, the reaction proceeded with high enantioselectivity even on a gram scale, and the product was transformed to a 5,6,7,8-tetrahydroisoquinoline bioactive molecule. Kinetic isotope effect (KIE) experiments indicated that C-H activation is the rate-determining step for the enantioselective C(sp3)-H arylation.
- Antilla, Jon C.,Jing, Hua-Qing,Kuninobu, Yoichiro,Li, Hong-Liang,Yang, Deng-Feng
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p. 1286 - 1291
(2022/02/25)
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- Palladium-Catalyzed Secondary C(sp3)?H Arylation of 2-Alkylpyridines
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A pyridyl group-assisted palladium-catalyzed secondary C(sp3)?H arylation protocol was developed. A substituent at the 3-position of the pyridyl group is proved to be important for promoting C?H arylation and controlling the regioselectivity. Aryl iodides can be used as coupling partners. The reaction proceeded in good to excellent yields with good functional group tolerance, even on the gram-scale. The preliminary asymmetric reaction was investigated using an L-proline derivative as a chiral ligand. (Figure presented.).
- Li, Hong-Liang,Kuninobu, Yoichiro
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p. 2637 - 2641
(2020/06/02)
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- Compound, organic electroluminescent element material, organic electroluminescent element, and electronic device
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A compound represented by general formula (A-0) or (B-0) is useful as an organic EL element material whereby it is possible to realize an organic EL element having long service life and high luminous efficiency even when driven at low voltage. (In the formulas, R1-R4, n1, m2, k3, k4, L0-L2, Ar1, and Ar2 are as defined in the specification.)
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Paragraph 0214; 0215; 0216; 0217
(2016/10/08)
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- AROMATIC AMINE DERIVATIVE, AND ORGANIC ELECTROLUMINESCENCE ELEMENT USING THE SAME
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Of a specific structure novel aromatic amine derivatives, and at least a light-emitting layer between a cathode and an anode including 1 layer or an organic thin film composed of one layer interposed in an organic electroluminescent element, said organic thin film least 1 layer, hole transport layer in particular said aromatic amine derivatives by itself or as a component of a mixture by, whether or not result in crystallization of molecules, organic electroluminescent device corresponding to a predetermined liquid crystal and, tube having a long lifetime in organic electroluminescent device with high.
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Paragraph 0312-0313
(2016/10/17)
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- AROMATIC AMINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENCE ELEMENT USING SAME
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An aromatic amine derivative represented by formula (1): wherein L1, L2, Ar1, Ar2, R1, R2, a, b, and Q are as defined in the specification. An organic electroluminescence device having at least one organic thin film layer which includes the aromatic amine derivative has high emission efficiency and long lifetime.
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Paragraph 0179; 0180; 0181
(2014/08/19)
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- AROMATIC AMINE DERIVATIVE, AND ORGANIC ELECTROLUMINESCENT ELEMENT COMPRISING SAME
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An aromatic amine derivative represented by the following formula (1), wherein at least one of Ar1 to Ar3 is represented by the following formula (2), wherein X1 to X3 are independently a nitrogen atom or CR2, provided that two of X1 to X3 are a nitrogen atom and X1 and X3 are not simultaneously a nitrogen atom.
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Paragraph 0109
(2013/05/22)
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- ELECTROACTIVE MATERIALS
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A compound having Formula I, Formula II, or Formula III: Ar1 may independently be phenylene, substituted phenylene, naphthylene, or substituted naphthylene. Ar2 is the same or different at each occurrence and is an aryl group. M is the same or different at each occurrence and is a conjugated moiety. T1 and T2 are independently the same or different at each occurrence and are conjugated moieties which are connected in a non-planar configuration; a and e are the same or different at each occurrence and are an integer from 1 to 6; b, c, and d are mole fractions such that b+c+d=1.0, with the proviso that c is not zero, and at least one of b and d is not zero, and when b is zero, M has at least two triarylamine units; and n is an integer greater than 1.
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Page/Page column 47
(2012/03/27)
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- AROMATIC AMINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT ELEMENT USING SAME
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There are provided an aromatic monoamine derivative having a fluorene structure-containing organic group and an aromatic hydrocarbon group-containing organic group, and an organic electroluminescent element containing an organic thin film layer composed of a single layer or plural layers while including at least a light emitting layer, the organic thin film layer being between a cathode and an anode, wherein at least one layer of the organic thin film layer, particularly a hole transport layer, contains the aromatic amine derivative alone or as a component of a mixture. An organic electroluminescent element which maintains high luminous efficiency even if exposed to a high temperature environment, and has a low driving voltage and a long emission lifetime, and an aromatic amine derivative capable of realizing the organic electroluminescent element are provided.
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Page/Page column 31
(2012/02/15)
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- AROMATIC AMINE DERIVATIVES AND ORGANIC ELECTROLUMINESCENT ELEMENTS USING SAME
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Provided are an organic EL device material capable of reducing the driving voltage of an organic EL device and increasing the lifetime of the device as compared with a conventional organic EL device material, specifically an aromatic amine derivative represented by N(Ara)(Arb)(Arc), and an organic EL device using the material. [Ara is represented by the formula (II). (In the formula (II): La represents a single bond or an arylene group; R1 to R4 each represent an alkyl group, an aryl group, or the like, and R3's or R4's, or R3 and R4 may be bonded to each other to form a ring; and o represents 0 to 3 and p represents 0 to 4.) Arb is represented by the formula (III). (in the formula (III), X represents NRa, O, or S, and Ra and R5 to R7 each represent an alkyl group, an aryl group, or the like, and R5's, R6's, or R7's adjacent to each other, or R5 and R6 may be bonded to each other to form a ring; n represents 2 to 4 when X represents NRa, and represents 0 to 4 when X represents O or S; and q represents 0 to 3, r and s each independently represent 0 to 4.) Arc represents an aryl group, or is represented by the formula (III).]
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Page/Page column 118-119
(2012/07/03)
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- AROMATIC AMINE DERIVATIVE, AND ORGANIC ELECTROLUMINESCENT ELEMENT
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Provided are: an aromatic amine derivative including a substituent A and a substituent B each represented by the formula (1) or (2) and having an arylene group bound to a carbazole structure, in which the substituent A and the substituent B include groups different from each other in the position at which the arylene group is bonded to the carbazole structure, and the substituent A and the substituent B are bonded to the same nitrogen atom or different nitrogen atoms in the molecule; an organic electroluminescent 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 a anode, in which at least one layer of the organic thin-film layer contains the aromatic amine derivative, and the molecules are rarely crystallized, the yield upon production of the organic electroluminescent device is improved, the driving voltage for the organic electroluminescent device is low, and the lifetime of the organic electroluminescent device is long; and an aromatic amine derivative which can realize the organic electroluminescent device. (In the formulae, each substituent is as described in claim 1.)
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Page/Page column 62
(2012/08/14)
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- AROMATIC AMINE DERIVATIVE, AND ORGANIC ELECTROLUMINESCENT ELEMENT COMPRISING SAME
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Provided are: an aromatic amine derivative having a terminal substituent selected from a dibenzofuran, a dibenzothiophene, a substituted carbazole, and a substituted fluorene bound to the central skeleton having a specific structure through a nitrogen atom; 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, in which at least one layer of the organic thin-film layer contains the aromatic amine derivative alone or as a component of a mixture, the organic electroluminescence device having a long lifetime and high luminous efficiency; and an aromatic amine derivative for realizing the device.
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Page/Page column 87
(2012/12/13)
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- ELECTROACTIVE MATERIALS
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A compound having Formula I, Formula II, or Formula III: Ar1 may independently be phenylene, substituted phenylene, naphthylene, or substituted naphthylene. Ar2 is the same or different at each occurrence and is an aryl group. M is the same or different at each occurrence and is a conjugated moiety. T1 and T2 are independently the same or different at each occurrence and are conjugated moieties which are connected in a non-planar configuration; a and e are the same or different at each occurrence and are an integer from 1 to 6; b, c, and d are mole fractions such that b+c+d=1.0, with the proviso that c is not zero, and at least one of b and d is not zero, and when b is zero, M has at least two triarylamine units; and n is an integer greater than 1.
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- AROMATIC AMINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
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An aromatic amine derivative having a specific structure. An organic electroluminescence device which is composed of one or more organic thin film layers sandwiched between a cathode and an anode, wherein at least one of the organic thin film layers especially a hole transporting layer, contains the aromatic amine derivative. The aromatic amine derivative has at least one substituted or unsubstituted dibenzofuran skeleton and at least one substituted or unsubstituted terphenylene skeleton. Because the molecules in the aromatic amine derivative hardly crystallize, organic electroluminescence devices improving their production yield and having prolonged lifetime are provided.
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Page/Page column 48
(2011/04/18)
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- AROMATIC AMINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
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Disclosed is a long-life organic EL device having high luminous efficiency even after storage at high temperatures. Also disclosed is an aromatic amine derivative which enables to realize such an organic EL device. The aromatic amine derivative is represented by the following general formula (1). (In the formula (1), Ar1 is represented by the general formula (2) below, and Ar2 is represented by the general formula (3) below.)
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Page/Page column 47
(2011/08/07)
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- AROMATIC AMINE DERIVATIVE, AND ORGANIC ELECTROLUMINESCENT ELEMENT
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Provided are an organic electroluminescence device that not only provides high efficiency but also has a long lifetime, and an aromatic amine derivative that realizes the device. The organic electroluminescence device includes an aromatic amine derivative, including at least one substituent A having dibenzofuran and at least one substituent B selected from groups each having dibenzofuran or carbazole, in a molecule thereof, in which the substituent A and the substituent B include groups different from each other, and the substituent A and the substituent B are bonded to the same nitrogen atom, or different nitrogen atoms, in the molecule. The molecules of the aromatic amine derivative hardly crystallize, which improves a yield in the production of the organic electroluminescence device. In the 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, the aromatic amine derivative is contained in at least one layer, particularly a hole transport layer, in the organic thin film layer.
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Page/Page column 71; 90
(2011/10/04)
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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 25; 37
(2012/01/11)
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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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- Asymmetric arylamine compounds and processes for making the same
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Novel asymmetric arylamine compounds useful as hole transport molecules (HTMs) incorporated into imaging members, such as layered photoreceptor devices, and improved chemical processes for making the same. The arylamine compounds increase the charge mobil
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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 50
(2008/12/04)
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- Aromatic amine derivative and organic electroluminescence device using same
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An aromatic amine compound having a specific structure, the following organic electroluminescence device and the noble aromatic amine compounds enable for realizing the device are provided. The device, which comprises at least one organic thin film layer comprising a light emitting layer sandwiched between a pair of electrode consisting of an anode and a cathode, wherein at least one of the organic thin film layers comprises the aromatic amine derivative singly or as its mixture component, exhibits various luminescent hue and has high heat resistance, a long lifetime, high luminance and high current efficiency. In particular, the device exhibits low decay of luminance based on driving it.
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Page/Page column 14
(2008/06/13)
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- Aromatic amine derivative and organic electroluminescence device employing the same
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A novel aromatic amine derivative having a specific structure and an organic electroluminescence device comprising an organic thin film layer which comprises at least one layer comprising at least a light emitting layer and is disposed between a cathode and an anode, wherein at least one layer in the organic thin film layer comprises the aromatic amine derivative singly or as a component of a mixture. The device can be driven under a decreased voltage and has a long life. The device can be realized by using the derivative.
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Page/Page column 19
(2010/11/27)
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- Biphenyl- and terphenyl-based recyclable organic trivalent iodine reagents
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Biphenyl- and terphenyl-based recyclable trivalent iodine reagents, such as 4-bromo-4′-(diacetoxyiodo)biphenyl, 4,4′-bis(diacetoxyiodo)biphenyl, 1,4-bis[4-(diacetoxyiodo)phenyl]benzene, 4-bromo-4′-[(hydroxy)(tosyloxy)iodo]biphenyl, 4,4′-bis[(hydroxy)(tosyloxy)iodo]biphenyl, were simply prepared and their reactivities for the oxidative rearrangement of ketones to esters, TEMPO-mediated oxidation of alcohols to aldehydes or ketones, oxidative dealkylation of N-alkylsulfonamides to sulfonamides, and α-tosyloxylation of ketones were compared with p-(diacetoxyiodo)toluene and p-[(hydroxy)(tosyloxy)iodo]toluene to show the same reactivities and, moreover, the biphenyl- and terphenyl-based iodoarenes formed were recovered by simple filtration of the reaction mixture in every reaction. Thus, these biphenyl- and terphenyl-based trivalent iodine reagents can be used as the recyclable reagents.
- Moroda, Atsushi,Togo, Hideo
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p. 12408 - 12414
(2007/10/03)
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- Synthesis of photo-crosslinkable hole-transport polymers with tunable oxidation potentials and their use in organic light-emitting diodes
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A series of photo-crosslinkable arylamine-based hole-transport copolymers has been synthesized. The synthetic methodology employed allows for the redox potential of the polymer to be tuned by the incorporation of electron-donating or -withdrawing moieties. Upon exposure to ultraviolet radiation, the polymers become insoluble, as evidenced by UV/Vis absorption spectroscopy, a feature that is useful for the fabrication of multilayer organic light-emitting diodes (OLEDs) by solution processing techniques. OLEDs based on these hole-transport polymers have been fabricated and the performance of the devices has been evaluated. The photo-crosslinking process has been optimized so that it no longer adversely impacts device performance.
- Hreha, Richard D.,Zhang, Ya-Dong,Domercq, Benoit,Larribeau, Nathalie,Haddock, Joshua N.,Kippelen, Bernard,Marder, Seth R.
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p. 1201 - 1212
(2007/10/03)
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- Aryl radicals from hexazadienes and tetrazenes
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Aryl radicals are produced from both ends of the hexazadienes 1 and 2 and from the tetrazene 3, either thermally or photolytically.They attack aromatic compounds in the nucleus, the yield of biaryl being in the range 40-70percent, though it can be made nearly quantitative by using m-dinitrobenzene as additive.The aryl radicals also oxidize 2-propanol to acetone, the reaction products being the halogenobenzene and 1,2-diacetylhydrazine.Photolysis of 1 goes mainly by way of the tetrazene 3, and this may also be a significant pathway in the thermal reaction.Azodiacetylis an intermediate in the thermal reaction of 1 with 2-propanol and may be generally so in all its reactions.Radical induced decomposition is believed to be important in the reactions of 1, 2, and 3, and it is probably responsible for the formation of 1-acetyl-1-arylhydrazines, routinely produced in yields up to 25percent.
- Mackay, Donald,McIntyre, Deane Douglas
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p. 990 - 999
(2007/10/02)
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