- Ir-catalyzed borylation of C-H bonds in N-containing heterocycles: Regioselectivity in the synthesis of heteroaryl boronate esters
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(Chemical Equation Presented) Blocking the way: Substitution at the 2-position in pyridines and other N-heterocycles blocks N-coordination to an Ir center. This steric hindrance provides a substrate-design criterion that allows the Ir-catalyzed borylation
- Mkhalid, Ibraheem A. I.,Coventry, David N.,Albesa-Jove, David,Batsanov, Andrei S.,Howard, Judith A. K.,Perutz, Robin N.,Marder, Todd B.
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- Silicon-containing substituted metal complex
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The invention discloses a silicon-containing substituted metal complex. The novel silicon-containing substituted metal complex has a general formula of M (La) m (Lb) n (Lc) q, and the ligand La is a ligand with silicon group substitution and can be used as a luminescent material in an electroluminescent device. The novel metal complexes have the advantages of remarkably improving the quantum efficiency of the material, effectively controlling the light-emitting wavelength and the light-emitting color and reducing the driving voltage, and can provide better device performance. The invention also discloses an electroluminescent device and a compound formulation.
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Paragraph 0188-0191; 0211; 0215-0217; 0224; 0228-0230
(2021/07/10)
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- Cyclo-aryl iridium compound and organic electroluminescence device using the compound
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The present invention discloses a cyclo-aryl iridium compound and a phosphorescent organic electroluminescence (organic EL) device using the cyclo-aryl iridium compound as a light-emitting dopant of the light-emitting layer. The organic EL device has good
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Paragraph 0056; 0066; 0067; 0068
(2018/04/03)
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- para-Selective C?H Borylation of (Hetero)Arenes by Cooperative Iridium/Aluminum Catalysis
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para-Selective C?H borylation of benzamides and pyridines has been achieved by cooperative iridium/aluminum catalysis. A combination of iridium catalysts commonly employed for arene C?H borylation and bulky aluminum-based Lewis acid catalysts provides an unprecedented strategy for controlling the regioselectivity of C?H borylation to give variously substituted (hetero)arylboronates, which are versatile synthetic intermediates for complex multi-substituted aromatic compounds.
- Yang, Lichen,Semba, Kazuhiko,Nakao, Yoshiaki
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supporting information
p. 4853 - 4857
(2017/04/11)
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- METAL COMPLEX AND ORGANIC LIGHT-EMITTING DEVICE
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A metal complex of formula (I): M(L1)x(L2)y (I) wherein: M is a second or third row transition metal; L1 in each occurrence is independently a light-emitting ligand; L2 is an auxiliary ligand; x is at least 1; y
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- Modular synthesis of simple cycloruthenated complexes with state-of-the-art performance in p-type DSCs
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A modular approach based on Suzuki-Miyaura cross coupling and Miyaura borylation has been used to prepare two cyclometallated [Ru(N N)2(C N)]+ complexes which possess either a carboxylic or phosphonic acid group attached via a phenylene spacer to the 4-position of the pyridine ring in the C N ligand. The key intermediate in the synthetic pathway is [Ru(bpy)2(1)]+ where bpy = 2,2′-bipyridine and H1 is 4-chloro-2-phenylpyridine. The crystal structure of [Ru(bpy)2(1)][PF6] is presented. Reaction of [Ru(bpy)2(1)][PF6] with 4-carboxyphenylboronic acid leads to [Ru(bpy)2(H6)][PF6], while the phosphonic acid analogue is isolated as the zwitterion [Ru(bpy)2(H5)]. The cyclometallated complexes have been characterized by mass spectrometry, multinuclear NMR spectroscopy, absorption spectroscopy and electrochemistry. [Ru(bpy)2(5)] adsorbs onto NiO FTO/NiO electrodes (confirmed by solid-state absorption spectroscopy) and its performance in p-type dye-sensitized solar cells (DSCs) has been compared to that of the standard dye P1; two-screen printed layers of NiO give better DSC performances than one layer. Duplicate DSCs containing [Ru(bpy)2(H5)] achieve short-circuit current densities (JSC) of 3.38 and 3.34 mA cm-2 and photoconversion efficiencies (η) of 0.116 and 0.109%, respectively, compared to values of JSC = 1.84 and 1.96 mA cm-2 and η = 0.057 and 0.051% for P1. Despite its simple dye structure, the performance of [Ru(bpy)2(H5)] parallels the best-performing cyclometallated ruthenium(ii) dye in p-type DSCs reported previously (He et al., J. Phys. Chem. C, 2014, 118, 16518) and confirms the effectiveness of a phosphonic acid anchor in the dye and the attachment of the anchoring unit to the pyridine (rather than phenyl) ring of the cyclometallating ligand.
- Brunner, Felix,Marinakis, Nathalie,Wobill, Cedric,Willgert, Markus,Ertl, Cathrin D.,Kosmalski, Tatjana,Neuburger, Markus,Bozic-Weber, Biljana,Glatzel, Thilo,Constable, Edwin C.,Housecroft, Catherine E.
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p. 9823 - 9833
(2016/11/02)
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- PHOSPHORESCENT MATERIALS
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Novel organic compounds containing a twisted aryl group are provided. In particular, the compounds provided contain a 2-phenylpyridine ligand having a twisted aryl group on the pyridine portion of the ligand. The compounds may be used in organic light emitting devices, particularly as emitting dopants. Devices comprising the compounds containing twisted aryl may demonstrate improved color, efficiency, stability and manufacturing. Additionally, methods are provided for making homoleptic Ir (III) compounds which may contain a twisted aryl.
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Paragraph 0166
(2015/11/16)
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- BASE METAL CATALYZED BORYLATION OF ARENES AND AROMMATIC HETEROCYCLES
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In one aspect, cobalt complexes are described herein. In some embodiments, such cobalt complexes employ bis(phosphine) or bis(imine) ligand and are operable as catalysts for borylation of arenes and aromatic heterocycles.
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Page/Page column 34
(2015/06/25)
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- Cobalt-catalyzed C-H borylation
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A family of pincer-ligated cobalt complexes has been synthesized and are active for the catalytic C-H borylation of heterocycles and arenes. The cobalt catalysts operate with high activity and under mild conditions and do not require excess borane reagents. Up to 5000 turnovers for methyl furan-2-carboxylate have been observed at ambient temperature with 0.02 mol % catalyst loadings. A catalytic cycle that relies on a cobalt(I)-(III) redox couple is proposed.
- Obligacion, Jennifer V.,Semproni, Scott P.,Chirik, Paul J.
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supporting information
p. 4133 - 4136
(2014/04/03)
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- Iridium-catalyzed C-H borylation of pyridines
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The iridium-catalysed C-H borylation is a valuable and attractive method for the preparation of aryl and heteroaryl boronates. However, application of this methodology for the preparation of pyridyl and related azinyl boronates can be challenged by low reactivity and propensity for rapid protodeborylation, particularly for a boronate ester ortho to the azinyl nitrogen. Competition experiments have revealed that the low reactivity is due to inhibition of the active catalyst through coordination of the azinyl nitrogen lone pair at the vacant site on the iridium. This effect can be overcome through the incorporation of a substituent at C-2. Moreover, when this is sufficiently electron-withdrawing protodeborylation is sufficiently slowed to permit isolation and purification of the C-6 boronate ester. Following functionalization, reduction of the directing C-2 substituent provides the product arising from formal ortho borylation of an unhindered pyridine ring. This journal is the Partner Organisations 2014.
- Sadler, Scott A.,Tajuddin, Hazmi,Mkhalid, Ibraheem A. I.,Batsanov, Andrei S.,Albesa-Jove, David,Cheung, Man Sing,Maxwell, Aoife C.,Shukla, Lena,Roberts, Bryan,Blakemore, David C.,Lin, Zhenyang,Marder, Todd B.,Steel, Patrick G.
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supporting information
p. 7318 - 7327
(2014/11/07)
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