- NIR organic dyes based on phenazine-cyanine for photoacoustic imaging-guided photothermal therapy
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As non-invasive diagnosis and therapy methods, photoacoustic (PA) imaging and photothermal therapy (PTT) have attracted extensive attention. Herein, two new acceptor-donor-acceptor near-infrared organic phenazine-cyanine dyes PH-1 and PH-2 were reported for photoacoustic imaging-guided photodynamic therapy. In the strong donor phenazine molecule, the electron-withdrawing indole salt unit was introduced for absorption to the near-infrared region. To improve water solubility, the two organic dyes were assembled with human serum albumin (HSA) to form nanoparticles of appropriate sizes, i.e., PH-1@HSA and PH-2@HSA, which showed excellent stability in both weakly acidic and weakly basic environments. Moreover, the results showed that PH-1@HSA and PH-2@HSA nanoparticles can effectively transform luminous energy to thermal energy in vitro and in vivo, and they can be utilized for PA imaging. Importantly, PH-1@HSA can accumulate in mice subcutaneous tumors by enhanced permeability and retention (EPR) and damage cancer tissues effectively.
- Yan, Yongchao,Chen, Jiawen,Yang, Zhijuan,Zhang, Xiao,Liu, Zhuang,Hua, Jianli
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- Highly efficient green organic light emitting diodes with phenanthroimidazole-based thermally activated delayed fluorescence emitters
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Here, a phenanthroimidazole moiety was firstly introduced into the construction of thermally activated delayed fluorescence (TADF) emitters, and two novel TADF emitters consisting of phenanthroimidazole as the acceptor group and phenazine as the donor group, 1-(4-(tert-butyl)phenyl)-2-(4-(10-phenylphenazin-5(10H)-yl)phenyl)-1H-phenanthro[9,10-d]imidazole (PPZTPI) and 1-phenyl-2-(4-(10-phenylphenazin-5(10H)-yl)phenyl)-1H-phenanthro[9,10-d]imidazole (PPZPPI) were designed and synthesized. The highly twisted conformation between phenazine and phenanthroimidazole in the molecules results in effective spatial separation of the HOMO and LUMO and small singlet-triplet splittings. Both compounds possess obvious TADF features. Their crystallographic properties, electronic structures, thermal stabilities, photophysical properties, and energy levels are studied systematically. Organic light-emitting diodes (OLEDs) using these two green TADF emitters demonstrate high external quantum efficiencies of 21.06% for PPZPPI and 20.52% for PPZTPI, respectively, which is comparable to most of the previously reported TADF OLEDs.
- Huang, Zhi,Xiang, Songpo,Zhang, Qing,Lv, Xialei,Ye, Shaofeng,Guo, Runda,Wang, Lei
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- Singlet and Triplet Contributions to the Excited-State Activities of Dihydrophenazine, Phenoxazine, and Phenothiazine Organocatalysts Used in Atom Transfer Radical Polymerization
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The photochemical dynamics of three classes of organic photoredox catalysts employed in organocatalyzed atom-transfer radical polymerization (O-ATRP) are studied using time-resolved optical transient absorption and fluorescence spectroscopy. The nine catalysts selected for study are examples of N-aryl and core-substituted dihydrophenazine, phenoxazine and phenothiazine compounds with varying propensities for control of polymerization outcomes. Excited singlet-state lifetimes extracted from the spectroscopic measurements are reported in N,N-dimethylformamide (DMF), dichloromethane (DCM), and toluene. Ultrafast (200 fs to 3 ps) electronic relaxation of the photocatalysts after photoexcitation at near-UV wavelengths (318-390 nm) populates the first singlet excited state (S1). The S1-state lifetimes range from 130 ps to 40 ns with a considerable dependence on the photocatalyst structure and the solvent. The competition between ground electronic state recovery and intersystem crossing controls triplet state populations and is a minor pathway in the dihydrophenazine derivatives but is of greater importance for phenoxazine and phenothiazine catalysts. A comparison of our results with previously reported O-ATRP performances of the various photoredox catalysts shows that high triplet-state quantum yields are not a prerequisite for controlling polymer dispersity. For example, the photocatalyst 5,10-bis(4-cyanophenyl)-5,10-dihydrophenazine, shown previously to exert good polymerization control, possesses the shortest S1-state lifetime (135 ps in DMF and 180 ps in N,N-dimethylacetamide) among the nine examples reported here and a negligible triplet-state quantum yield. The results call for a re-evaluation of the excited-state properties of most significance in governing the photocatalytic behavior of organic photoredox catalysts in O-ATRP reactions.
- Bhattacherjee, Aditi,Sneha, Mahima,Lewis-Borrell, Luke,Amoruso, Giordano,Oliver, Thomas A.A.,Tyler, Jasper,Clark, Ian P.,Orr-Ewing, Andrew J.
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- Formation of 5,10-dihydrophenazine from phenazine by Pseudomonas cepacia IFO 15124 at low oxygen tensions
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5,10-Dihydrophenazine (H2Phen) was formed from phenazine (Phen) by Pseudomonas cepacia IFO 15124 in growing cultures at low oxygen tensions. Effects of culture conditions on microbial reduction of Phen with this strain were investigated. Under optimized conditions, the transformation of Phen to H2Phen by this strain gave the molar conversion yield of 30%. However, H2Phen was not detected in the culture medium when the strain was incubated with Phen with sufficient aeration.
- Kawashima, Hideki,Ogawa, Satoshi
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- Cross-linking Effects on Performance Metrics of Phenazine-Based Polymer Cathodes
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Developing cathodes that can support high charge–discharge rates would improve the power density of lithium-ion batteries. Herein, the development of high-power cathodes without sacrificing energy density is reported. N,N′-diphenylphenazine was identified as a promising charge-storage center by electrochemical studies due to its reversible, fast electron transfer at high potentials. By incorporating the phenazine redox units in a cross-linked network, a high-capacity (223 mA h g?1), high-voltage (3.45 V vs. Li/Li+) cathode material was achieved. Optimized cross-linked materials are able to deliver reversible capacities as high as 220 mA h g?1 at 120 C with minimal degradation over 1000 cycles. The work presented herein highlights the fast ionic transport and rate capabilities of amorphous organic materials and demonstrates their potential as materials with high energy and power density for next-generation electrical energy-storage technologies.
- Gannett, Cara N.,Peterson, Brian M.,Shen, Luxi,Seok, Jeesoo,Fors, Brett P.,Abru?a, Héctor D.
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- A robust phenazine-containing organic polymer as catalyst for amine oxidative coupling reactions
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Here we present the design and synthesis of a new robust microporous organic polymer (TPBP) decorated with phenazine groups which endowed reversibly redox-active properties. The obtained TPBP possesses relatively high surface area (359 m2/g) and good thermal stability. TPBP exhibits excellent catalytic capability for the oxidative homocoupling of amines with high activity and selectivity toward target products. Besides, this metal-free catalyst demonstrated excellent recyclability after 6 cycles under the investigated conditions. By means of EPR and UV-vis spectroscopy, a plausible mechanism of the amine oxidative coupling reaction was deduced via a single electron transfer from TPBP radical cations to amine substrates.
- Guo, Zhiyong,Lin, Junyu,Zhan, Hongbing
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- Dihydrophenazine linked porous organic polymers for high capacitance and energy density pseudocapacitive electrodes and devices
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Redox porous organic polymers are promising pseudocapacitive materials. However, their specific capacitance still needs further elevation. Herein, we report a novel dihydrophenazine derived porous organic polymer, GT-POP-1. The GT-POP-1 based electrode and asymmetric device show high specific capacitance and energy density metrics of 97.1 mF cm?2and 7.3 μW h cm?2
- Zhang, Huanhuan,Tang, Xiaohui,Gu, Cheng
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- Controlled emission colors and singlet-triplet energy gaps of dihydrophenazine-based thermally activated delayed fluorescence emitters
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We have developed thermally activated delayed fluorescence (TADF) emitters containing 5,10-dihydrophenazine as an electron donor and various electron-acceptor units. The TADF emitters exhibit wide ranges of emission colors from green to orange, singlet-triplet energy gaps ΔEST of ~0-0.19 eV, and delayed fluorescence lifetimes τd of 0.1-50 μs. An organic light-emitting diode containing one of the TADF emitters exhibits a maximum external quantum efficiency (EQE) of 12%, which is higher than those obtained with conventional fluorescent emitters. Time-resolved photoluminescence measurements of the compounds in a host matrix reveal that TADF makes a large contribution to the EQE of the devices. Our findings provide guidelines for modulating ΔEST and τd of TADF emitters.
- Lee, Jiyoung,Shizu, Katsuyuki,Tanaka, Hiroyuki,Nakanotani, Hajime,Yasuda, Takuma,Kaji, Hironori,Adachi, Chihaya
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- Dihydrophenazine-based double-anchoring dye for dye-sensitized solar cells
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A novel dihydrophenazine-based organic di-anchoring dye DK-11 was synthesized by utilizing a simple synthetic protocol. The dye was characterized by optical and electrochemical studies and used as a sensitizer for dye-sensitized solar cell. The proposed butterfly structure was supported by IR experiments which ensured the binding of both carboxylic acid units on the semiconductor surface. Using the dye DK-11, the device generated an efficiency of 5.07% with JSC, VOC, and FF values of 10.65 mA/cm2, 0.67 V, and 0.71, respectively.
- Kumar, Dhirendra,Chen, Yu-Lin,Tsai, Chih-Hung,Wong, Ken-Tsung
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- Post-Synthetic Modification of Metal-Organic Frameworks Bearing Phenazine Radical Cations for aza-Diels-Alder Reactions
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Metal-organic frameworks (MOFs) consisting of organic radicals are of great interest because they have exhibited unique and intriguing optical, electronic, magnetic, and chemo-catalytic properties, and thus have demonstrated great potential applications in optical, electronic, and magnetic devices, and as catalysts. However, the preparation of MOFs bearing stable organic radicals is very challenging because most organic radicals are highly reactive and difficult to incorporate into the framework of MOFs. Herein we reported a post-synthetic modification strategy to prepare a novel MOF containing phenazine radical cations, which was used as heterogeneous catalyst for aza-Diels-Alder reaction. The zinc-based metal-organic framework Zn2(PHZ)2(dabco) (N) was successfully synthesized from 5,10-di(4-benzoic acid)-5,10-dihydrophenazine (PHZ), triethylene diamine (dabco) with Zn(NO3)2 ? 6H2O by solvothermal method. The as-synthesized MOF N was partially oxidized by AgSbF6 to form MOF R containing ~10% phenazine radical cation species. The resultant MOF R was found to keep the original crystal type of N and very persistent under ambient conditions. Consequently, MOF R was successfully employed in radical cation-catalyzed aza-Diels-Alder reactions with various imine substrates at room temperature with high reaction conversion. Moreover, heterogeneous catalyst MOF R was reusable up to five times without much loss of catalytic activity, demonstrating its excellent stability and recyclability. Therefore, the post-synthetic modification developed in this work is expected to become a versatile strategy to prepare radical-based MOFs for the application of heterogeneous catalysts in organic synthesis.
- Jiang, Wei-Ling,Huang, Bin,Wu, Meng-Xiang,Zhu, Ye-Kai,Zhao, Xiao-Li,Shi, Xueliang,Yang, Hai-Bo
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supporting information
p. 3985 - 3992
(2021/11/01)
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- Concerted Multiproton-Multielectron Transfer for the Reduction of O2to H2O with a Polyoxovanadate Cluster
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The concerted transfer of protons and electrons enables the activation of small-molecule substrates by bypassing energetically costly intermediates. Here, we present the synthesis and characterization of several hydrogenated forms of an organofunctionalized vanadium oxide assembly, [V6O13(TRIOLNO2)2]2-, and their ability to facilitate the concerted transfer of protons and electrons to O2. Electrochemical analysis reveals that the fully reduced cluster is capable of mediating 2e-/2H+ transfer reactions from surface hydroxide ligands, with an average bond dissociation free energy (BDFE) of 61.6 kcal/mol. Complementary stoichiometric experiments with hydrogen-atom-accepting reagents of established bond strengths confirm that the electrochemically established BDFE predicts the 2H+/2e- transfer reactivity of the assembly. Finally, the reactivity of the reduced polyoxovanadate toward O2 reduction is summarized; our results indicate a stepwise reduction of the substrate, proceeding through H2O2 en route to the formation of H2O. Kinetic isotope effect experiments confirm the participation of hydrogen transfer in the rate-determining step of both the reduction of O2 and H2O2. This work constitutes the first example of hydrogen atom transfer for small-molecule activation with reduced polyoxometalates, where both electron and proton originate from the cluster.
- Brennessel, William W.,Fertig, Alex A.,Matson, Ellen M.,McKone, James R.
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p. 15756 - 15768
(2021/10/02)
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- PHENAZINE COPOLYMERS AND USES THEREOF
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Provided are phenazine copolymers and methods of making and using phenazine copolymers. The phenazine copolymers may be made from one or more phenazine precursors and one or more co-monomer precursors, one or more phenazine precursors and one or more cross-linking precursors, or one or more phenazine precursors and both one or more cross-linking precursors and one or more co-monomer precursors. The phenazine copolymers may be used in/on cathodes. The cathodes may be used in a variety of devices, such as, for example, batteries or supercapacitors.
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Paragraph 0099; 0137
(2020/10/20)
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- Phenazine Radical Cations as Efficient Homogeneous and Heterogeneous Catalysts for the Cross-Dehydrogenative Aza-Henry Reaction
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The redox activity of molecular phenazine catalysts has been previously exploited for aerobic oxidative amine homo- and cross-coupling reactions. In this contribution, we have extended the reaction scope of this novel type of organocatalyst and used them in the cross-dehydrogenative aza-Henry coupling of isoquinolines with nitromethane under aerobic conditions. Additionally, we have designed and prepared a novel porous organic polymer by cross-linking of tetrakis(4-bromophenyl)silane and dihydrophenazine through Pd-catalyzed Buchwald-Hartwig cross-coupling. This new type of heterogeneous catalyst, apart from being robust and easily reusable, also showed outstanding catalytic activities and improved selectivity compared to its molecular counterpart. A plausible reaction mechanism was proposed based on spectroscopic and kinetic measurements.
- Unglaube, Felix,Hünem?rder, Paul,Guo, Xuewen,Chen, Zixu,Wang, Dengxu,Mejía, Esteban
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- Aromatic compound and organoelectroluminescent device comprising the compound
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The present invention relates to a novel aromatic compound and an organic electroluminescent device comprising the same. The present invention relates to an organic electroluminescent device including an aromatic compound. (by machine translation)
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Paragraph 0159-0165
(2019/12/10)
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- Phenanthro imidazole structure has the thermal delay fluorescent material and its preparation method and application (by machine translation)
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The invention belongs to the photoelectric material applied science and technology field, in particular to an imidazole structure west of the thermotropic delay fluorescent material, its application and electroluminescent device. This kind of material is rich in electron and hole of phenanthro imidazole structure and phenazino structure through the aromatic group is bridged and formed, is a satisfied at the same time radiation transition constant kr bigger and single triplet energy gap Δ EST Of small delay fluorescent material. Intensive donor - receptor group combined effectively avoids the electronic device with the hole carrier density imbalance caused by the triplet state of the - charge reaction energy loss, thereby improving the device [...] problem. In addition, the Philippines and imidazole structure and phenazino structure can effectively increase the orbital overlap at the same time increase the rigidity of the molecule, thereby inhibiting the non-radiation transition, effectively improve the light emitting efficiency of the device, is a kind of fine light-emitting layer and the guest material leaves the photosphere material, and the luminescent layer body material. (by machine translation)
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Paragraph 0085-0086; 0088
(2019/10/17)
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- A Dual-Ion Organic Symmetric Battery Constructed from Phenazine-Based Artificial Bipolar Molecules
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Symmetric batteries received an increasing research interest in the past few years because of their simplified fabrication process and reduced manufacturing cost. In this study, we propose the first dual-ion organic symmetric cell based on a molecular anion of 4,4′-(phenazine-5,10-diyl)dibenzoate. The alkali salt of 4,4′-(phenazine-5,10-diyl)dibenzoate allows a facile transport of cations and large anions, and remains stable in both oxidized and reduced states. The large potential difference between phenazine and benzoate results in a high cell voltage of 2.5 V and an energy density of 127 Wh kg?1 at a current rate of 1 C. The introduction of bipolar organic materials may further consolidate the development of symmetric batteries that are fabricated from abundant elements and environmentally friendly materials.
- Dai, Gaole,He, Yan,Niu, Zhihui,He, Ping,Zhang, Changkun,Zhao, Yu,Zhang, Xiaohong,Zhou, Haoshen
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supporting information
p. 9902 - 9906
(2019/05/10)
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- Birch-Type Photoreduction of Arenes and Heteroarenes by Sensitized Electron Transfer
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The direct reduction of arenes and heteroarenes by visible-light irradiation remains challenging, as the energy of a single photon is not sufficient for breaking aromatic stabilization. Shown herein is that the energy accumulation of two visible-light photons allows the dearomatization of arenes and heteroarenes. Mechanistic investigations confirm that the combination of energy-transfer and electron-transfer processes generates an arene radical anion, which is subsequently trapped by hydrogen-atom transfer and finally protonated to form the dearomatized product. The photoreduction converts planar aromatic feedstock compounds into molecular skeletons that are of use in organic synthesis.
- Chatterjee, Anamitra,K?nig, Burkhard
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supporting information
p. 14289 - 14294
(2019/08/30)
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- Hydrogen on Cobalt Phosphide
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Cobalt phosphide (CoP) is one of the most promising earth-abundant replacements for noble metal catalysts for the hydrogen evolution reaction (HER). Critical to HER is the binding of H atoms. While theoretical studies have computed preferred sites and energetics of hydrogen bound to transition metal phosphide surfaces, direct experimental studies are scarce. Herein, we describe measurements of stoichiometry and thermochemistry for hydrogen bound to CoP. We studied both mesoscale CoP particles, exhibiting phosphide surfaces after an acidic pretreatment, and colloidal CoP nanoparticles. Treatment with H2 introduced large amounts of reactive hydrogen to CoP, ca. 0.2 H per CoP unit, and on the order of one H per Co or P surface atom. This was quantified using alkyne hydrogenation and H-atom transfer reactions with phenoxy radicals. Reactive H atoms were even present on the as-prepared materials. On the basis of the reactivity of CoP with various molecular hydrogen donating and accepting reagents, the distribution of binding free energies for H atoms on CoP was estimated to be roughly 51-66 kcal mol-1 (δG°H 0 to -0.7 eV vs H2). Operando X-ray absorption spectroscopy gave preliminary indications about the structure of hydrogenated CoP, showing a slight lattice expansion and no significant change of the effective nuclear charge of Co under H2-flow. These results provide a new picture of catalytically active CoP, with a substantial amount of reactive H atoms. This is likely of fundamental relevance for its catalytic and electrocatalytic properties. Additionally, the approach developed here provides a roadmap to examine hydrogen on other materials.
- Delley, Murielle F.,Wu, Zishan,Mundy, M. Elizabeth,Ung, David,Cossairt, Brandi M.,Wang, Hailiang,Mayer, James M.
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supporting information
p. 15390 - 15402
(2019/11/02)
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- Hydrogenation of N-Heteroarenes Using Rhodium Precatalysts: Reductive Elimination Leads to Formation of Multimetallic Clusters
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A rhodium-catalyzed method for the hydrogenation of N-heteroarenes is described. A diverse array of unsubstituted N-heteroarenes including pyridine, pyrrole, and pyrazine, traditionally challenging substrates for hydrogenation, were successfully hydrogenated using the organometallic precatalysts, [(η5-C5Me5)Rh(N-C)H] (N-C = 2-phenylpyridinyl (ppy) or benzo[h]quinolinyl (bq)). In addition, the hydrogenation of polyaromatic N-heteroarenes exhibited uncommon chemoselectivity. Studies into catalyst activation revealed that photochemical or thermal activation of [(η5-C5Me5)Rh(bq)H] induced C(sp2)-H reductive elimination and generated the bimetallic complex, [(η5-C5Me5)Rh(μ2,η2-bq)Rh(η5-C5Me5)H]. In the presence of H2, both of the [(η5-C5Me5)Rh(N-C)H] precursors and [(η5-C5Me5)Rh(μ2,η2-bq)Rh(η5-C5Me5)H] converted to a pentametallic rhodium hydride cluster, [(η5-C5Me5)4Rh5H7], the structure of which was established by NMR spectroscopy, X-ray diffraction, and neutron diffraction. Kinetic studies on pyridine hydrogenation were conducted with each of the isolated rhodium complexes to identify catalytically relevant species. The data are most consistent with hydrogenation catalysis prompted by an unobserved multimetallic cluster with formation of [(η5-C5Me5)4Rh5H7] serving as a deactivation pathway.
- Kim, Sangmin,Loose, Florian,Bezdek, Máté J.,Wang, Xiaoping,Chirik, Paul J.
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p. 17900 - 17908
(2019/11/19)
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- Aerobic Oxidative Homo- and Cross-Coupling of Amines Catalyzed by Phenazine Radical Cations
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Phenazine radical cations (PhRCs) were used for the first time as efficient metal-free catalysts for the oxidative homo- and cross-coupling of a variety of different amines. A series of functional PhRCs were prepared, characterized with X-ray diffraction, and their radical character was investigated with DFT calculations. They were tested as catalysts under neat conditions with low oxygen pressure to prepare homo- and cross-coupled aliphatic and aromatic imines in high yields. Although all synthesized phenazines were catalytically active, the highest reaction rates and the best selectivity were achieved using the 5,10-dihydro-5,10-dimethylphenazine radical cation. By means of fluorescence, UV-vis and EPR spectroscopy, a mechanism of the oxidative amine coupling, catalyzed by PhRCs, is proposed.
- Bri?ar, Rok,Unglaube, Felix,Hollmann, Dirk,Jiao, Haijun,Mejía, Esteban
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p. 13481 - 13490
(2018/11/02)
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- COMPOSITIONS AND METHODS OF PROMOTING ORGANIC PHOTOCATALYSIS
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The invention provides novel compounds and methods that are useful in promoting reactions that proceed through an oxidative quenching pathway. In certain embodiments, the reactions comprise atom transfer radical polymerization.
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Paragraph 0117
(2018/09/12)
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- Ultrafast Observation of a Photoredox Reaction Mechanism: Photoinitiation in Organocatalyzed Atom-Transfer Radical Polymerization
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Photoredox catalysis has driven a revolution in the field of organic chemistry, but direct mechanistic insights into reactions of genuine synthetic utility remain relatively scarce. Herein we report ultrafast time-resolved spectroscopic observation of a bimolecular organocatalyzed photoredox reaction, from catalyst photoexcitation through to photoinduced electron transfer (PET) and intermediate formation, using transient vibrational and electronic absorption spectroscopy with sub-picosecond time resolution. Specifically, the photochemical dynamics of initiation in organocatalyzed atom-transfer radical polymerization (O-ATRP) are elucidated for two complementary photoredox organocatalysts (N,N-diaryl-5,10-dihydrophenazines). Following photoexcitation, a dissociative bimolecular electron transfer is observed from the first excited singlet state of both photocatalysts to methyl 2-bromopropionate in dichloromethane, toluene, and dimethylformamide. The photocatalyst excited donor state, ground state, and radical cation are tracked in real time alongside the debrominated radical fragment. Our work challenges previously proposed mechanisms of initiation in O-ATRP and indicates that PET from short-lived excited singlet states can exert control of polymer molecular weight and dispersity by suppressing the steady-state concentration of the reactive debrominated radical. More broadly, we aim to demonstrate the potential of ultrafast absorption spectroscopy to observe directly transient, open-shell intermediates in mechanistic studies of photoredox catalysis.
- Koyama, Daisuke,Dale, Harvey J. A.,Orr-Ewing, Andrew J.
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supporting information
p. 1285 - 1293
(2018/02/09)
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- Photoelectric functional material based on phosphine sulfur/oxygen modifying phenazine
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The invention discloses a photoelectric functional material based on phosphine sulfur/oxygen modifying phenazine. In the material, R1 and R2 are alkyl chains or aryl groups and derivatives thereof, and X1 and X2 are sulphur atoms or oxygen atoms. The alkyl chains are any one of methyl, ethyl, isopropyl, tertiary butyl, n-butyl, cyclohexane or hexamethylene. The aryl groups and derivatives thereofare any one of phenyl group, 4-methyl phenyl, 3,5-dimethyl phenyl, 2,4,6-trimethyl phenyl, 4-methoxyl phenyl, 4-isopropoxy phenyl, 4-methoxyl-3,5-dimethyl phenyl, naphthaline-1-yl or furan-2-yl. The method has the advantages that the synthesis steps are simple, the raw materials are low toxic, cheap and easy to get, the synthesis method has the good compatibility on functional groups, and the atomic economy is high, and the obtained product has the wide potential application value in the photoelectric material field, and is hopeful to be applied to the field of photoelectric materials.
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Paragraph 0039-0042
(2018/12/02)
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- A containing phenazino functional siloxane and its synthetic method
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The invention discloses a functional siloxane containing phenazine and a synthetic method thereof. The synthetic method comprises the following steps: (1) synthetizing 5,10-dihydrophenazine by taking phenazine and sodium hydrosulfite as raw materials; (2) synthetizing 5,10-dihydrophenazine-5-carbamyl chloride by taking 5,10-dihydrophenazine and triphosgene as raw materials; (3) reacting the carbamyl chloride compound with 3-aminopropyltriethoxysilane to obtain a functional siloxane compound containing phenazine, which is proved to be the functional siloxane containing phenazine by infrared spectroscopy and H-NMR determination. The compound structurally contains a plurality of functional groups, namely siloxane, amide, carbamido, phenazine and the like, and has potential application value in the aspects such as drug sustained release, a molecular imprinting identification material, a rare-earth luminescent material, white carbon black modification and the like. According to the synthetic method disclosed by the invention, the production efficiency is high, the synthetic path is short and the preparation technology is simple.
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Paragraph 0041-0042
(2017/05/04)
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- Efficient Hydrogenation of Nitrogen Heterocycles Catalyzed by Carbon-Metal Covalent Bonds-Stabilized Palladium Nanoparticles: Synergistic Effects of Particle Size and Water
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We reveal here the first hydrogenation of nitrogen heterocycles catalyzed by carbon–metal covalent bonds-stabilized palladium nanoparticles in water under mild conditions. Using a one-phase reduction method, smaller metal–carbon covalent bond-stabilized Pd nanoparticles were prepared with a size distribution of 2.5±0.5 nm, which showed extraordinary synergistic effects with water in the catalytic hydrogenation of nitrogen heterocycles. Water was supposed to accelerate substrate absorption and synergistic activation of molecular hydrogen on the Pd nanoparticles surface. The nanosized Pd catalyst could be easily recovered and reused for 5 runs. (Figure presented.).
- Zhang, Yu,Zhu, Jie,Xia, Yun-Tao,Sun, Xiao-Tao,Wu, Lei
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supporting information
p. 3039 - 3045
(2016/10/09)
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- Modular metal-carbon stabilized palladium nanoparticles for the catalytic hydrogenation of N-heterocycles
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We report here the first modular metal-carbon stabilized palladium nanoparticles based on binaphthyl scaffolds, which can be prepared from palladium salts and substituted binaphthyl diazonium salts in homogeneous system through direct reduction using sodium borohydride. The resulting palladium nanoparticles subjected to the electron density of modular moieties are found to be novel and efficient catalysts for the catalytic hydrogenation of N-heterocycles, affording the corresponding adducts in good to excellent yields under mild conditions.
- Zhang, Yu,Mao, Mao,Ji, Yi-Gang,Zhu, Jie,Wu, Lei
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p. 329 - 332
(2016/01/12)
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- LIGHT-EMITTING MATERIAL FOR ORGANIC ELECTROLUMINESCENT DEVICE, ORGANIC ELECTROLUMINESCENT DEVICE USING SAME, AND MATERIAL FOR ORGANIC ELECTROLUMINESCENT DEVICE
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In the present invention, disclosed are a novel aromatic compound with outstanding light-emitting efficiency and heat stability, a manufacturing method thereof and an organic electronic device including the novel aromatic compound. For this, in the present invention, provided are a ring-formed aromatic compound and a novel aromatic amine derivative denoted by chemical formula 1 for improving performance of the device.COPYRIGHT KIPO 2015
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Paragraph 0161-0163
(2016/10/17)
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- The material for the organic electroluminescence device
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The present invention relates to compounds according to formula (1) and formula (2), said compounds being suitable for use in electronic devices, in particular organic electroluminescent devices.
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Paragraph 0091-0092
(2017/01/02)
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- MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES
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The present invention relates to compounds according to formula (1) and formula (2), said compounds being suitable for use in electronic devices, in particular organic electroluminescent devices.
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- Palladium-Catalyzed Coupling of Sulfonylhydrazones with Heteroaromatic 2-Amino-Halides (Barluenga Reaction): Exploring the Electronics of the Sulfonylhydrazone
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This paper describes a new reactivity of the Pd-catalyzed coupling of 2-amino-3-bromo-aromatic and heteroaromatic compounds with sulfonylhydrazones (Barluenga reaction).The new catalyst system and modulation of the electronic nature of hydrazone that were needed for successful reaction are described herein.
- Tan, Hongyu,Houpis, Ioannis,Liu, Renmao,Wang, Youchu,Chen, Zhilong,Fleming, Matthew J.
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supporting information
p. 1044 - 1048
(2015/09/01)
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- Palladium-catalyzed domino double n-arylations (inter- and intramolecular) of 1,2-diamino(hetero)arenes with o,o-dihalo(hetero)arenes for the synthesis of phenazines and pyridoquinoxalines
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Domino reactions for the synthesis of phenazines have been developed that start from 1,2-diaminoarenes and 1,2-dihaloarenes and proceed through palladium-catalyzed double N-arylations (inter- and intramolecular) followed by an in situ oxidation. A variety of functional groups, which include base-sensitive groups, were well tolerated under the optimized reaction conditions to afford phenazines in good to excellent yields. The protocol was extended to the synthesis of pyridoquinoxalines by employing either o-phenylenediamines and 2,3-dihalopyridines or 1,2-diaminopyridines and 1,2-dihaloarenes. Domino reactions for the synthesis of phenazines have been developed that start from 1,2-diaminoarenes and 1,2-dihaloarenes and proceed through palladium-catalyzed double N-arylations (inter- and intramolecular) followed by an in situ oxidation. The protocol was extended to the synthesis of pyridoquinoxalines. Copyright
- Laha, Joydev K.,Tummalapalli, K.S. Satyanarayana,Gupta, Ankur
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p. 8330 - 8335
(2014/01/06)
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- TRICYCLIC HETEROAROMATIC COMPOUNDS AS ALPHA-SYNUCLEIN LIGANDS
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Derivatives of phenothiazine, phenoxazine, and phenazine compounds and their use as α-synuclein ligands are described. Also described are methods of using these compounds and their radiolabeled analogs for the detection, monitoring, and treatment of synucleinopathies, including Parkinson's disease.
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Paragraph 0217
(2013/12/04)
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- Palladium catalyzed coupling of tosylhydrazones with aryl and heteroaryl halides in the absence of external ligands: Synthesis of substituted olefins
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Palladium catalyzed cross-coupling reaction of hydrazones with aryl halides in the absence of external ligand is reported. The versatility of this coupling reaction is demonstrated in showcasing the selectivity of coupling reaction in the presence of hydr
- Ojha, Devi Prasan,Prabhu, Kandikere Ramaiah
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p. 11027 - 11033
(2013/02/22)
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- 2,2'-biimidazole as an efficient ligand for copper(I)-catalyzed C-N coupling reactions
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An efficient copper(I)-catalyzed system using 2,2'-biimidazole as the ligand was applied to N-arylation of a broad spectrum of nitrogen nucleophiles with aryl halides. The reactions were carried out in relatively mild conditions with good to excellent yields.
- Hu, Zhang,Ye, Wei,Zou, Hongbin,Yu, Yongping
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experimental part
p. 222 - 228
(2010/04/02)
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- Oxidation of 2-alkyl-5,10-dihydrophenazines
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Oxidation of 2-alkyl-5,10-dihydrophenazines afforded 1:1 molecular complexes of the initial compounds with the corresponding 2-alkylphenazines. 2004 MAIK "Nauka/Interperiodica".
- Bidman
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p. 1433 - 1434
(2007/10/03)
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- Novel derivatives and analogues of galanthamin
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New compounds of general formula I 1
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- One pot synthesis of 5,10-dihydrophenazine compounds and 5,10-substituted dihydrophenazines
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Dihydrophenazines and bis(dihydrophenazines) are prepared in high yield under commercially viable reaction conditions by reacting a catechol with a 1,2-diaminoaryl compound, wherein either the catechol or the 1,2-diaminoaryl compound is provided in at least 50% molar stoichiometric excess. The product may be oxidized to the corresponding phenazine, but is preferably derivatized at one or both of the 5,10-positions to form a monosubstituted or disubstituted dihydrophenazine or bis(dihydrophenazine). Most preferably, 5,10-dialkyl-5,10-dihydrophenazines are prepared starting from catechol and 1,2-diaminoaryl compound in a one pot synthesis. The products are useful as dyes, and in particular as chromophores in electrochromic systems.
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- Synthesis of N-Acylated Derivatives of 5,10-Dihydrophenazine
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A family of N-mono- and N,N'-diacylated 5,10-dihydrophenazines (4-26) was prepared by reaction of 5,10-dihydrophenazine (1) or the corresponding 5,10-bis(trimethylsilyl) derivative (3) with acyl chlorides. 5,10-Bis(4-nitrobenzoyl)-5,10-dihydrophenazine (11) was hydrogenated to the new aromatic diamine 21 which is an interesting starting material for polymer syntheses. - Key words: Phenazines, 5,10-dihydro-
- Mikulla, Markus,Muelhaupt, Rolf
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p. 1723 - 1728
(2007/10/02)
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- Preparation and Properties of Electron Donor Acceptor Complexes of the Compounds having Capto-dative Substituents
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In order to examine the "capto-dative" substitution-effect on the electrical conductivity, five compounds which have capto-dative substituents were prepared.Electron withdrawing (capto) group was nitro- or cyano-substituted phenyl and electron donating (dative) one was 5-methyl-5,10-dihydrophenazinyl moiety.The character of intramolecular electron donor acceptor complex of the five compounds were demonstrated by their uv spectra.Electron donor acceptor complexes of them with tetracyanoquinodimethane were prepared and their electrical resistivities were measured.
- Sugimoto, Akira,Kotani, Takeshi,Tsujimoto, Junko,Yoneda, Shigeo
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p. 435 - 438
(2007/10/02)
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- Electron-transfer Reductions by Active Aldehydes catalysed by Thiazolium Salt in the Presence of Triethylamine
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3-Benzylthiazolium salts, in methanol containing triethylamine, catalyse the redox reaction in which aldehydes are oxidized to methyl esters concurrently with the reduction of several organic compounds.
- Inoue, Hiroo,Higashiura, Kunihiko
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p. 549 - 550
(2007/10/02)
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