- Vascular barrier protective effects of 3-N- or 3-O-cinnamoyl carbazole derivatives
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In this Letter, we investigated the barrier protective effects of 3-N-(MeO)n-cinnamoyl carbazoles (BS 1; n = 1, BS 2; n = 2, BS 3; n = 3) and 3-O-(MeO)3-cinnamoyl carbazole (BS 4) against high-mobility group box 1 (HMGB1)-mediated vascular disruptive responses in human umbilical vein endothelial cells (HUVECs) and in mice for the first time. Data showed that BS 2, BS 3, and BS 4, but not BS 1, inhibited HMGB1-mediated vascular disruptive responses and transendothelial migration of human neutrophils to HUVECs. BS 2, BS3, and BS 4 also suppressed HMGB1-induced hyperpermeability and leukocyte migration in mice. Interestingly, the barrier protective effects of BS 3 and BS 4 were better than those of BS 2. These results suggest that the number of methoxy groups substituted on the cinnamamide or cinnamate moiety of the 9H-3-carbazole derivative is an important pharmacophore for the barrier protective effects of these compounds.
- Ku, Sae-Kwang,Lee, Jee-Hyun,Yuseok,Lee, Wonhwa,Song, Gyu-Yong,Bae, Jong-Sup
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- Ruthenium catalyzed remote C4-selective C-H functionalisation of carbazoles: Via σ-activation
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We report the C4-selective C-H alkylation of carbazole derivatives furnished with a pyrimidine directing group at N9. This was realized using ruthenium catalyzed σ-activation methodology, whereby C-H activation at C1 enables the interaction of this ruthenacycle, at the para position to the metal center, with tertiary alkyl radicals.
- Leitch, Jamie A.,Heron, Callum J.,McKnight, Janette,Kociok-K?hn, Gabriele,Bhonoah, Yunas,Frost, Christopher G.
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- Multichromophore Molecular Design for Thermally Activated Delayed-Fluorescence Emitters with Near-Unity Photoluminescence Quantum Yields
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Three multichromophore thermally activated delayed fluorescence (TADF) molecules, p-di2CzPN, m-di2CzPN, and 1,3,5-tri2CzPN, were synthesized and characterized. These molecules were designed by connecting the TADF moiety 4,5-di(9H-carbazol-9-yl)phthalonitrile (2CzPN) to different positions of a central benzene ring scaffold. Three highly soluble emitters all exhibited near-quantitative photoluminescence quantum yields (φPL) in toluene. High φPLs were also achieved in doped films, 59 and 70% for p-di2CzPN and m-di2CzPN in 10 wt % DPEPO doped film, respectively, and 54% for 1,3,5-tri2CzPN in 20 wt % doped CBP films. The rate constant of reverse intersystem crossing (kRISC) for p-di2CzPN and m-di2CzPN in DPEPO films reached 1.1 × 105 and 0.7 × 105 s-1, respectively, and kRISC for 1,3,5-tri2CzPN in the CBP film reached 1.7 × 105 s-1. A solution-processed organic light-emitting diode based on 1,3,5-tri2CzPN exhibited a sky-blue emission with CIE coordinates of (0.22, 0.44) and achieved a maximum external quantum efficiency of 7.1%.
- Chen, Dongyang,Kusakabe, Yu,Ren, Yongxia,Sun, Dianming,Rajamalli, Pachaiyappan,Wada, Yoshimasa,Suzuki, Katsuaki,Kaji, Hironori,Zysman-Colman, Eli
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- Thermally cross-linkable thermally activated delayed fluorescent materials for efficient blue solution-processed organic light-emitting diodes
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Solution-processed organic light-emitting diodes (OLEDs) have attracted great attention due to their simple fabrication process and easy scalability of the solution process. In this work, a thermally cross-linkable thermally activated delayed fluorescent (TADF) molecule DV-MOC-DPS was designed and synthesized. Moreover, a thermally cross-linkable host material DV-CDBP with high triplet energy was also synthesized. With the incorporation of two cross-linkable vinylbenzyl ether groups, both these materials with excellent thermal stabilities can be fully cross-linked after heating at 180 °C. In addition, the cross-linked films with the different mass ratios of DV-CDBP and DV-MOC-DPS (1:0.06, 1:0.09 and 1:0.12) were investigated. The cross-linked films are quite smooth with the root-mean-square (RMS) roughness in the range from 0.622 nm to 0.725 nm. Simultaneously, the cross-linked film with a mass ratio of 1:0.09 exhibits the highest photoluminescence quantum yield of 0.71. By employing the cross-linked films as emitting layers, an efficient blue solution-processed OLED with a maximum external quantum efficiency of 2.0% was achieved. The molecular design reported here provides a novel route toward highly efficient solution-processed OLEDs.
- Sun, Kaiyong,Xie, Xiafei,Liu, Yao,Jiang, Wei,Ban, Xinxin,Huang, Bin,Sun, Yueming
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- Vinyl-type polynorbornene with 9,9′-(1,1′-biphenyl)-4,4′- diylbis-9H-carbazole side groups as a host material for highly efficient green phosphorescent organic light-emitting diodes
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The soluble polynorbornene (P1) bearing 9,9′-(1,1′-biphenyl)-4, 4′-diylbis-9H-carbazole (CBP) side groups was investigated as a host material for green emitters in phosphorescent OLED devices. The vinyl addition polymerization of norbornene monomers using Pd(ii) catalyst efficiently produces P1 in combination with 1-octene chain transfer agent. P1 exhibits high thermal stability with high decomposition (Td5 > 451°C) and glass transition temperatures (Tg > 361°C). The HOMO (ca. -5.5 eV) and LUMO (ca. -2.1 eV) levels with the triplet energy of ca. 2.60 eV suggest that P1 is suitable for a host material for green emitters. The solution-processed devices based on the emissive layers containing P1 host doped with various concentration of fac-Ir(ppy)3 (1-6 wt%) display stable green emission of fac-Ir(ppy)3 with high device performances. The external quantum efficiency and power efficiency reach 7.2% and 11 lm/W, respectively, at the optimum doping concentration of fac-Ir(ppy)3 (2 wt%). The device performances are found to be slightly lower than those of PhOLED with molecular CBP host but higher than those of a PVK-based device. It is shown that in conjunction with the good processability of polynorbornene backbones, the high levels of the effective hole and electron mobilities of P1 (ca. 10-3 and 10-5 cm2/Vs, respectively) as well as large triplet energy inherited from CBP side groups are mainly responsible for the high performance of the phosphorescent OLEDs with solution-processed P1 host:emitter layers.
- Park, Jun Ha,Yun, Changhun,Koh, Tae-Wook,Do, Youngkyu,Yoo, Seunghyup,Lee, Min Hyung
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- Comparison of Carbazole and Fluorene Donating Effects on the Two-Photon Absorption and Nitric Oxide Photorelease Capabilities of a Ruthenium–Nitrosyl Complex
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A ruthenium–nitrosyl derivative of formula [RuII(CzT)(bipy)(NO)](PF6)3 [CzT = 4′-(N-ethylcarbazol-3-yl)-2,2′:6′,2′′-terpyridine, bipy = 2,2′-bipyridine] has been synthesized and fully characterized, and compared with the previously reported [RuII(FT)(bipy)(NO)](PF6)3 complex [FT = 4′-(9,9-dihexyl-9H-fluoren-2-yl)-2,2′:6′,2′′-terpyridine]. Additionally, the X-ray crystal structure of [RuII(CzT)(bipy)(NO2)](PF6), the precursor of [RuII(CzT)(bipy)(NO)](PF6)3, is reported. The presence of a tertiary amine in the carbazole unit leads to redshifted charge-transfer transitions towards the electron-withdrawing Ru–NO fragment and hence enhanced two-photon absorption (TPA) properties. In contrast, the quantum yield of the NO· photorelease process is lower for the carbazole-containing complex. The issue of optimization of the TPA versus NO·-release capabilities is addressed.
- Enriquez-Cabrera, Alejandro,Lacroix, Pascal G.,Sasaki, Isabelle,Mallet-Ladeira, Sonia,Farfán, Norberto,Barba-Barba, Rodrigo M.,Ramos-Ortiz, Gabriel,Malfant, Isabelle
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- Simultaneous discrimination of diameter, handedness, and metallicity of single-walled carbon nanotubes with chiral diporphyrin nanocalipers
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We have been developing the methodology to discriminate the handedness and diameter of single-walled carbon nanotubes (SWNTs) through molecular recognition using chiral diporphyrin nanotweezers. Although relatively small diameters of SWNTs (1.0 nm. In this context, we designed chiral diporphyrin with a much larger cavity, namely, "nanocalipers". The feature of the newly designed host molecule is: (1) long spacer with more than 1.4 nm consisting of three aromatic moieties; (2) nearly parallel orientation of the two porphyrins; (3) restricted conformation by biaryl linkages of the porphyrin-carbazole and carbazole-anthracene; (4) strong interaction of two porphyrins and anthracene with the surface of a SWNT through π-π stacking; and (5) stereogenic centers at the periphery of porphyrins discriminating helicity of SWNTs. As expected, we obtained optically active SWNTs with >1.0 nm in diameter and, unexpectedly, enriched metallic SWNTs over semiconducting ones. The optically active metallic SWNTs are identified for the first time, in addition to the optically active semiconducting SWNTs with such large diameters. The nanocalipers are found to recognize the diameter, handedness, and metallicity of SWNTs simultaneously.
- Liu, Gang,Wang, Feng,Chaunchaiyakul, Songpol,Saito, Yukie,Bauri, Ajoy K.,Kimura, Takahide,Kuwahara, Yuji,Komatsu, Naoki
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- Novel carbazole-based main chain polymeric metal complexes containing complexes of phenanthroline with Zn(II) or Cd(II): Synthesis, characterization and photovoltaic application in DSSCs
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In this work, four main chain polymeric complexes(P1-P4), with fluorene or phenylethyl linked with carbazole as electron donor, phenanthroline metal complexes as a electron withdrawing unit, were synthesized through simple synthetic procedures and with low cost. They were characterized by FT-IR, Elemental analysis, GPC. The UV-vis absorption spectroscopy, photoluminescence spectroscopy, cyclic voltammetry are also determined and studied. Dye-sensitized solar cells (DSSCs) based on P1-P4 as the dye sensitizers exhibit some conversion efficiencies. It was found that the incorporation of 2,7-divinyl-9,9-dioctylfluorene unit instead of 1,4-divinyl-2-methoxyl-5- octyloxybenzene unit results in a negative shift of the lowest unoccupied molecular orbital(LUMO) levels for P3 and P4, in comparison to P1and P2, which induces a remarkable enhancement of the electron injection driving force from the excited polymer sensitizers to the TiO2 semiconductor. Moreover, when the coordinated ion of the polymer complexes changed from zinc ion to cadmium ion, a bathochromically shifted maximum absorption band can be realized, which consequently results in an increased light harvesting efficiency and photogenerated current. All of these dyes performed as sensitizers for the DSSCs test under AM 1.5 similar experimental conditions, and a maximum solar-to-electric power-conversion efficiency (PCE) is up to 1.15% (J sc = 2.71 mA cm-2, Voc = 0.649 eV, FF = 0.653).
- Zhou, Jun,Yu, Xiaoguang,Jin, Xueliang,Tang, Guipeng,Zhang, Wei,Hu, Jiaomei,Zhong, Chaofan
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- Carbazole-based D-π-A molecules: Determining the photophysical properties and comparing ICT effects of π-spacer and acceptor groups
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4-(9′-Hexylcarbazol-3′-yl)benzaldehyde (Cz-Ph-CHO: 4) and 4-(9′-hexylcarbazol-3′-yl)benzylidenemalononitrile (Cz-Ph-CN: 5) were synthesised with the structure of D-π-A, where carbazole, phenylene and formyl/dicyanovinyl groups act as electron donor (D), pi-spacer (π) and electron acceptor (A) units, respectively. The thermal, electrochemical, optical and intramolecular charge transfer (ICT) properties of compounds 4 and 5 were investigated. Compounds 4 and 5, in particular their ICT behaviour, were also compared with the closely related structure, 2-(9′-hexylcarbazol-3′-yl)-5-pyridinecarbaldehyde (Cz-Py-CHO: 7). For the purpose of tuning chemical structure to obtain targeted properties, electrochemical data and absorption and emission measurements suggest that the dicyanovinyl unit in compound 5 is a better acceptor than formyl in compound 4, and that pyridine in compound 7 is a better π-spacer than benzene in compound 4, in exerting ICT characteristics such as fluorosolvatochromism and Stokes shifts.
- Altinolcek, Nuray,Battal, Ahmet,Vardalli, Cemre Nur,Tavasli, Mustafa,Yu, Holly A.,Peveler, William J.,Skabara, Peter J.
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- An Upgraded “Two-in-One” Strategy toward Highly Crystalline Covalent Organic Frameworks
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A highly crystalline bicarbazole-based covalent organic framework (BCzP-COF) was synthesized via an upgraded “two-in-one” strategy by the self-polycondensation of A2B2 monomer with two neopentyl acetal and two amine groups. Such a strategy is propitious to afford higher crystallinity, larger special surface areas and better morphology than that of using unprotected monomer with free aldehydes and amines. Additionally, the off-white powder of BCzP-COF could serve as acidichromism sensor with a significant color change. Intriguingly, the conductivity of the protonated BCzP-COF can improve by six orders of magnitude compared to that of the pristine samples. This work has the potential to lead to bicarbazole-functional materials for chemosensors and electronic devices.
- Chen, Dan,Chen, Weiben,Xing, Guolong,Zhang, Ting,Chen, Long
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- Structure-activity relationship of bromoeudistomin D, a powerful Ca2+ releaser in skeletal muscle sarcoplasmic reticulum
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Bromoeudistomin D and 9-methyl-7-bromoeudistomin D which have a β-carboline skeleton are powerful Ca2+ releasers from skeletal muscle sarcoplasmic reticulum exhibiting caffeine-like properties. We examined the effects of bromoeudistomin D analogues on Ca2+-induced Ca2+ release from skeletal muscle sarcoplasmic reticulum. Among bromoeudistomin D analogues, the Ca2+-releasing activities of carboline derivatives were higher than those of carbazole derivatives, suggesting that a carboline skeleton is significantly important for the manifestation of Ca2+-releasing activity and Ca2+ sensitivity of Ca2+-induced Ca2+ release. On the contrary, the analogues which have a carbazole skeleton and bromine at C-6 inhibit both Ca2+- and caffeine-induced Ca2+ release. 9-Methyl-substitution of the analogue elevated its Ca2+-releasing activity. Moreover, there is a close correlation between the enhancement of [3H]ryanodine binding to sarcoplasmic reticulum by the analogues and the activation of Ca2+ release by them. Bromoeudistomin D analogues may provide valuable information about the structure-function relationship of the ryanodine receptor/Ca2+ release channels in skeletal muscle sarcoplasmic reticulum.
- Takahashi, Yukiko,Furukawa, Ken-Ichi,Ishibashi, Masami,Kozutsumi, Daisuke,Ishiyama, Haruaki,Kobayashi, Jun'ichi,Ohizumi, Yasushi
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- Carbazole-based two-photon fluorescent probe for selective imaging of mitochondrial hydrogen peroxide in living cells and tissues
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This paper reported a two-photon fluorescent probe for mitochondrial H2O2 detection and imaging based on the incorporation of a sensing boronate ester and an organelle-targeting triphenylphosphonium moiety onto the carbazole fluorophore. The probe exhibits a fast “turn on” response, good selectivity toward H2O2 and high specificity for mitochondria.
- Zhang, Kai,Wu, Wei,Li, Yinhui,Sun, Mingtai,Yu, Huan,Wong, Man Shing
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p. 115298 - 115302
(2016)
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- Light-Emitting Electrochemical Cells and Solution-Processed Organic Light-Emitting Diodes Using Small Molecule Organic Thermally Activated Delayed Fluorescence Emitters
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Two novel charged organic thermally activated delayed fluorescence (TADF) emitters, 1 and 2, have been synthesized. Their TADF behavior is well-supported by the multiexponential decay of their emission (nanosecond and microsecond components) and the oxygen dependence of the photoluminescence quantum yields. Spin-coated electroluminescent devices have been fabricated to make light-emitting electrochemical cells (LEECs) and organic light-emitting diodes (OLEDs). The first example of a non-doped charged small organic molecule LEEC is reported and exhibited an external quantum efficiency (EQE) of 0.39% using 2. With a multilayer architecture, a solution-processed OLED device using neat 2 as the emitting layer gave an EQE of 5.1%, the highest reported to date for a nondoped solution-processed small molecule organic TADF OLED. These promising results open up a new area in light-emitting materials for the development of low-cost TADF LEECs.
- Wong, Michael Y.,Hedley, Gordon J.,Xie, Guohua,K?lln, Lisa S.,Samuel, Ifor D. W.,Pertegás, Antonio,Bolink, Henk J.,Zysman-Colman, Eli
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- Nine-ring angular fused biscarbazoloanthracene displaying a solid state based excimer emission suitable for OLED application
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A new biscarbazoloanthracene consisting of nine fused aromatic rings, including two pyrrole units, has been obtained in a straightforward and convergent synthesis. Computational chemistry and conformational analysis revealed that the semiconductor's molecule is not planar, the two carbazole moieties being helical twisted from the plane of the anthracene unit. Photophysical and electrochemical measurements showed that this angular fused heteroacene has a low lying HOMO energy level with a wide band gap despite its extended π-conjugated molecular framework. Based on its relatively low-lying HOMO level, the semiconductor promises a high environmental stability in comparison to other related linear fused acenes and heteroacenes. The biscarbazoloanthracene has been applied as the light emitting layer in a white light emitting diode (WOLED). It is proposed that the white OLED feature is due to dual light emission properties from the active semiconductor layer being based on both the molecular luminescence of the small molecule and a discrete excimer emission made possible by suitable aggregates in the solid state. Noteworthy, this is the first reported example of such a behavior observed in a small molecule heteroacene rather than an oligomer or a polymer.
- Baryshnikov, Gleb V.,Gawrys, Pawel,Ivaniuk, Khrystyna,Witulski, Bernhard,Whitby, Richard J.,Al-Muhammad, Ayham,Minaev, Boris,Cherpak, Vladyslav,Stakhira, Pavlo,Volyniuk, Dmytro,Wiosna-Salyga, Gabriela,Luszczynska, Beata,Lazauskas, Algirdas,Tamulevicius, Sigitas,Grazulevicius, Juozas V.
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- Effects of donors of bodipy dyes on the performance of dye-sensitized solar cells
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A new series of donor-acceptor-π-linker-acceptor (D–A–π–A) featured organic dyes containing Bodipy derivative as the auxiliary acceptor, furan unit as the π conjugated spacer, and 2-cyanoacrylic acid as the anchor group were synthesized and applied in dye-sensitized solar cells (DSSCs). The incorporated electron-withdrawing unit of Bodipy enhances light harvesting by decreasing the molecular energy gap and red-shifting absorption spectra. For comparison, three different arylamine chromophores namely 3-methoxy-9H-carbazole (CBZ-B), triphenylamine (TPA-B) and phenoxazine (POZ-B) were separately appended onto the 6-position of Bodipy unit to study the effect of the electron donating groups on device performance. The UV–vis absorption spectra, electrochemical properties, density functional theory calculation, photovoltaic properties and electrochemical impedance measurements of DSSCs with these three dyes were systematically investigated. The Bodipy dyes have broad absorption spectra covering the range of 250–700?nm with the highest molar extinction coefficient up to >55?000?M?1?cm?1. The molecular energy level tuning can be conveniently accomplished by alternating the donor moiety. The DSSCs based on TPA-B showed the best photovoltaic performance: a maximum monochromatic incident photon-to-current conversion efficiency (IPCE) of 70%, a short-circuit photocurrent density (Jsc) of 13.95?mA?cm?2, an open-circuit photovoltage (Voc) of 557?mV, and a fill factor (ff) of 0.61, corresponding to an overall conversion efficiency of 4.76% under standard global AM 1.5G solar light conditions. Our research demonstrates that Bodipy based D–A–π–A molecular architecture is a highly promising class for the improvement of the performance of DSSCs in the future.
- Mao, Mao,Li, Qing-Song,Zhang, Xiao-Lin,Wu, Guo-Hua,Dai, Chun-Guang,Ding, Yong,Dai, Song-Yuan,Song, Qin-Hua
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- Fluorescent pyrene-centered starburst oligocarbazoles with excellent thermal and electrochemical stabilities
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A series of pyrene-centered starburst oligocarbazoles (1-3) have been synthesized and well characterized. Based on photophysical, thermal and electrochemical studies in solutions and as thin films, all starburst molecules reveal a sky blue emission with a high efficiency (ΦF = 0.99 - 0.81) and excellent thermal and electrochemical stabilities. As OLED materials, these superior properties are helpful to enhance device stability and lifetime.
- Ren, Ming-Guang,Guo, Hui-Jun,Qi, Fei,Song, Qin-Hua
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- Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties
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Two novel carbazole-based compounds 7a and 7b were synthesised as potential candidates for application in organic electronics. The materials were fully characterised by NMR spectroscopy, mass spectrometry, FTIR, thermogravimetric analysis, differential scanning calorimetry, cyclic voltammetry, and absorption and emission spectroscopy. Compounds 7a and 7b, both of which were amorphous solids, were stable up to 291 °C and 307 °C, respectively. Compounds 7a and 7b show three distinctive absorption bands: high and mid energy bands due to locally excited (LE) transitions and low energy bands due to intramolecular charge transfer (ICT) transitions. In dichloromethane solutions compounds 7a and 7b gave emission maxima at 561 nm and 482 nm with quantum efficiencies of 5.4% and 97.4% ± 10%, respectively. At positive potential, compounds 7a and 7b gave two different oxidation peaks, respectively: quasi-reversible at 0.55 V and 0.71 V, and reversible at 0.84 V and 0.99 V. At negative potentials, compounds 7a and 7b only exhibited an irreversible reduction peak at -1.86 V and -1.93 V, respectively.
- Altinolcek, Nuray,Battal, Ahmet,Peveler, William J.,Skabara, Peter J.,Tavasli, Mustafa,Yu, Holly A.
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- Bipolar iridium dendrimers containing carbazolyl dendron and 1,2,4-triazole unit for solution-processed saturated red electrophosphorescence
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Two solution-processable, carbazole-based iridium dendrimers (Ir-1 and Ir-2) were synthesized and characterized. The presence of carbazolyl substituent on the cyclometallated ligand resulted in improved solubility, good control over intermolecular interactions, and improved hole transport properties. The triazole ancillary ligand led to improved electron transport properties. When the dendrimers were employed as host-free light-emitting layers in the OLEDs, the devices exhibited a low turn-on voltage of 5.4 V. The maximal external quantum efficiencies and luminous efficiency of the devices obtained from Ir-1 and Ir-2 were 5.1% and 3.3 cd A-1 and 7.9% and 4.4 cd A-1, respectively, both with saturated red emission (CIE coordinates, 0.663, 0.332). The devices have a structure of indium tin oxide/poly(3,4- ethylenedioxythiophene)/dendrimer/1,3,5-tris(N-phenylbenzimiazole-2-yl)benzene/ cesium fluoride/aluminum. Given ease of synthesis and good device performance, these iridium dendrimers can be used to fully exploit the potential of low-cost OLEDs, leading to more applications in high-efficiency OLEDs.
- Liang, Bo,Hu, Sujun,Liu, Yanping,Fan, Zhiqiang,Wang, Xueye,Zhu, Weiguo,Wu, Hongbin,Cao, Yong
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- A new class of solid state ionic conductors for application in all solid state dye sensitized solar cells
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Solid state ionic conductors based on a carbazole-imidazolium cation structure were synthesized for application in solid state dye sensitized solar cells. Solid state electrolytes using designed solid state ionic conductors and iodine provide dual channels for hole/triiodide transportation, giving rise to a good conversion efficiency of 2.85%. The Royal Society of Chemistry.
- Midya, Anupam,Xie, Zhibin,Yang, Jia-Xiang,Chen, Zhi-Kuan,Blackwood, Daniel J.,Wang, John,Adams, Stefan,Loh, Kian Ping
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- Determination and reduction of translocator protein (TSPO) ligand rs6971 discrimination
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The 18 kDa translocator protein (TSPO) is a target for development of diagnostic imaging agents for glioblastoma and neuroinflammation. Clinical translation of TSPO imaging agents has been hindered by the presence of a polymorphism, rs6971, which causes a non-conservative substitution of alanine for threonine at amino acid residue 147 (TSPO A147T). Disclosed brain-permeant second-generation TSPO ligands bind TSPO A147T with reduced affinity compared to the wild type protein (TSPO WT). Efforts to develop a TSPO ligand that binds TSPO WT and TSPO A147T with similarly high affinity have been hampered by a lack of knowledge about how ligand structure differentially influences interaction with the two forms of TSPO. To gain insight, we have established human embryonic kidney cell lines stably over-expressing human TSPO WT and TSPO A147T, and tested how modifications of a novel N-alkylated carbazole scaffold influence affinity to both TSPO isoforms. Most of the new analogues developed in this study showed high affinity to TSPO WT and a 5-6-fold lower affinity to TSPO A147T. Addition of electron-withdrawing substituents yielded analogues with highest affinity for TSPO A147T without decreasing affinity for TSPO WT. This knowledge can be used to inform further development of non-discriminating TSPO ligands for use as diagnostic markers for glioblastoma and neuroinflammation irrespective of rs6971.
- Sokias, Renee,Werry, Eryn L.,Chua, Sook W.,Reekie, Tristan A.,Munoz, Lenka,Wong, Erick C. N.,Ittner, Lars M.,Kassiou, Michael
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- Block and Random Living, Ring-Opening Metathesis Copolymerization of Functionally Differentiated Carbazole-Containing Norbornene Monomers
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The synthesis of novel diblock polymers containing both a potential charge transport and a non-linear optic block has been accomplished. The synthesis exploits the living, ring-opening metathesis block copolymerization of two norbornene type monomers, one of which contains an unsubstituted N-carbazolyl ring while the other has a bromo substituent at the 3-position of the carbazole ring. Conversion of the bromo functionality to a 2,2-dicyanovinyl group introduces the non-linear optic property. The first monomer was prepared by the previously reported efficient cation radical Diels-Alder cycloaddition of N-trans-1-propenylcarbazole to 1,3-cyclopentadiene, while the second was obtained by N-bromosuccinimide bromination of the first monomer. For purposes of comparison, the corresponding random copolymer was also synthesized.
- Roh, Yeonsuk,Bauld, Nathan L.
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- Functionalization of biphenylcarbazole (CBP) with siloxane-hybrid chains for solvent-free liquid materials
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We report herein the synthesis of siloxane-functionalized CBP molecules (4,4′-bis(carbazole)-1,1′-biphenyl) for liquid optoelectronic applications. The room-temperature liquid state is obtained through a convenient functionalization of the molecules with heptamethyltrisiloxane chains via hydrosilylation of alkenyl spacers. The synthesis comprises screening of metal-catalyzed methodologies to introduce alkenyl linkers into carbazoles (Stille and Suzuki Miyaura cross-couplings), incorporate the alkenylcarbazoles to dihalobiphenyls (Ullmann coupling), and finally introduce the siloxane chains. The used conditions allowed the synthesis of the target compounds, despite the high reactivity of the alkenyl moieties bound to π-conjugated systems toward undesired side reactions such as polymerization, isomerization, and hydrogenation. The features of these solvent-free liquid CBP derivatives make them potentially interesting for fluidic optoelectronic applications.
- Correia, Gabriel,Heinrich, Beno?t,Méry, Stéphane,Mager, Lo?c,Polychronopoulou, Kyriaki,Ribierre, Jean-Charles,Shaya, Janah
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- Preparation method of 3 - bromo - N - phenyl carbazole
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The invention relates to a preparation method of 3 -bromo - N -phenyl carbazole, and belongs to the technical field of organic chemistry. To the invention, diphenylamine serves as a starting raw material, and 2 -bromophenylaniline is obtained through bromination reaction. Then, intramolecular cyclization is carried out to obtain carbazole. Then, 3 - bromocarbazole is obtained by bromination reaction. Finally, a substituted 3 - bromo - N -phenyl carbazole is obtained. By controlling the concentration and reaction environment of the reactants, the selectivity of the reaction site is effectively improved, the used raw materials are simple and easy to obtain, the preparation period is relatively short, and the reaction process is simple and easy to control.
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Paragraph 0024; 0030-0031; 0039; 0045-0046
(2021/10/11)
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- Predictable site-selective functionalization: Promoter group assistedpara-halogenation ofN-substituted(hetero)aromatics under metal-free condition
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Herein, regioselectivepara-C-H halogenation ofN-pyrimidyl (hetero)aromatics through SEAr (electrophilic aromatic substitution) type reaction is disclosed. SEAr type reaction has been utilized for the C5-bromination of indolines (para-selective) withN-bromosuccinimide under metal and additive-free conditions in good to excellent yields. The developed methodology is also applicable for iodination and challenging chlorination. The pyrimidyl group is identified as a reactivity tuner that also controls the regioselectivity. The present method is also applicable for selective halogenation of aniline, pyridine, indole, oxindole, pyrazole, tetrahydroquinoline, isoquinoline, and carbazole. DFT studies such as Fukui nucleophilicity and natural charge maps also support the observedp-selectivity. Post-functionalization of the title compound into the corresponding arylated, olefinated, and dihalogenated products is achieved in a one-pot, two-step fashion. Late-stage C-H bromination was also executed on drug/natural molecules (harmine, etoricoxib, clonidine, and chlorzoxazone) to demonstrate the applicability of the developed protocol.
- Gupta, Shiv Shankar,Manisha,Kumar, Rakesh,Dhiman, Ankit Kumar,Sharma, Upendra
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p. 9675 - 9687
(2021/12/01)
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- Aromatic compound and organoelectroluminescent device comprising the compound
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The present invention relates to an aromatic compound and an organic electroluminescent device including the same. The aromatic compound is represented by chemical formula 1, and the organic electroluminescent device is excellent in driving voltage, luminous efficiency and lifetime characteristics.
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Paragraph 0486-0491
(2021/08/31)
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- Halogenated method of aromatic compound
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The invention belongs to the field of organic synthesis, and particularly relates to synthesis of aromatic halogens, in particular to arylamine. The invention discloses a synthesis method of a corresponding ortho-halogenated product from aromatic compounds such as carbazole and phenol. The method comprises the following steps: adding a metal sulfonate salt catalyst, aromatic amine, carbazole, phenol and other hydrogen - heteroatom-containing aromatic compound reaction substrates, a halogenation reagent and a reaction solvent at a specific reaction temperature. After the drying agent is dried, the yield of the reaction product and the nuclear magnetic characterization determining structure are determined by column chromatography. The reaction product yield is determined by gas chromatography. By adopting the method, under the cheap metal salt catalyst, a plurality of ortho-substituted brominated and chloro products can be obtained with moderate to excellent yield.
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Paragraph 0189-0194; 0230-0232; 0238
(2021/11/10)
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- Convenient One-Pot Synthesis of 9 H -Carbazoles by Microwave Irradiation Employing a Green Palladium-Based Nanocatalyst
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An efficient palladium-catalyzed tandem reaction for the one-pot synthesis of 9 H -carbazoles under microwave irradiation is developed. This approach involves a sequential Buchwald-Hartwig amination and a direct arylation from affordable and inexpensive anilines and 1,2-dihaloarenes. For the development of this purpose, a novel and magnetically recoverable palladium nanocatalyst supported on a green biochar under ligand-free conditions is used. Compared to other existing palladium-based protocols, the present synthetic methodology shows a drastic reduction in reaction times and excellent compatibility with different functional groups allowing to obtain a small library of 9 H -carbazoles in high yields and with good regioselectivity. This procedure represents the first example in the direct synthesis of carbazoles using a heterogeneous palladium nanocatalyst from commercial precursors. To examine the application of this protocol, a direct and scalable synthesis of the bioactive carbazole alkaloid clausenalene from commercially available starting materials is described.
- Steingruber, H. Sebastián,Mendioroz, Pamela,Volpe, María A.,Gerbino, Darío C.
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p. 4048 - 4058
(2021/08/03)
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
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Discloses a novel compound capable of improving the luminous efficiency, stability and lifetime of an element, and an organic electronic element, or an electronic device using the same. (by machine translation)
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Paragraph 0147; 0154-0159
(2020/06/13)
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- Heterocyclic com pounds and organic light-emitting diode including the same
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The present invention relates to a novel heterocyclic compound and an organic electroluminescent device comprising the same. The heterocyclic compound is represented by the following Chemical Formula 1, and the organic electroluminescent device including the heterocyclic compound has excellent driving voltage, luminous efficiency, and lifespan properties. Chemical Formula 1. (by machine translation)
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Paragraph 0494; 0512-0517
(2021/01/19)
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- Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to Assisted-Tandem Catalysis to Construct N-Containing Fused Heteroarenes
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An aerobic dehydrogenation of nitrogen-containing heterocycles catalyzed by Grubbs catalyst is developed. The reaction is applicable to various nitrogen-containing heterocycles. The exceptionally high functional group compatibility of this method was confirmed by the oxidation of an unprotected dihydroindolactam V to indolactam V. Furthermore, by taking advantage of the oxygen-mediated structural change of the Grubbs catalyst, we integrated ring-closing metathesis and subsequent aerobic dehydrogenation to develop the novel assisted-tandem catalysis using molecular oxygen as a chemical trigger. The utility of the assisted-tandem catalysis was demonstrated by the concise synthesis of N-containing fused heteroarenes including a natural antibiotic, pyocyanine.
- Kawauchi, Daichi,Noda, Kenta,Komatsu, Yoshiyuki,Yoshida, Kei,Ueda, Hirofumi,Tokuyama, Hidetoshi
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supporting information
p. 15793 - 15798
(2020/10/12)
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- Combined KOH/BEt3Catalyst for Selective Deaminative Hydroboration of Aromatic Carboxamides for Construction of Luminophores
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The selective catalytic C-N bond cleavage of amides into value-added amine products is a desirable but challenging transformation. Molecules containing iminodibenzyl motifs are prevalent in pharmaceutical molecules and functional materials. Here we established a combined KOH/BEt3 catalyst for deaminative hydroboration of acyl-iminodibenzyl derivatives, including nonheterocyclic carboxamides, to the corresponding amines. This novel transition-metal-free methodology was also applied to the construction of Clomipramine and luminophores.
- Li, Jinshan,Wang, Jiali,Yang, Jianguo,Yao, Wubing,Zhong, Aiguo
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p. 8086 - 8090
(2020/11/03)
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- 9-Aryl-3-aminocarbazole as an Environment- and Stimuli-Sensitive Fluorogen and Applications in Lipid Droplet Imaging
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Environment-sensitive luminophoric molecules have played an important role in the fields of smart materials, sensing, and bioimaging. In this study, it was demonstrated that depending on the substituents, 9-aryl-3-aminocarbazoles can display aggregation-induced emission and solvatofluorochromism, and the operating mechanism was clarified. The application of these compounds to lipid droplet imaging and fluorescent probes for cysteamine was demonstrated.
- Matsubara, Ryosuke,Kaiba, Tomoaki,Nakata, Akito,Yabuta, Tatsushi,Hayashi, Masahiko,Tsubaki, Motonari,Uchino, Takashi,Chatani, Eri
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p. 5535 - 5547
(2019/05/10)
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- Cu-mediated selective bromination of aniline derivatives and preliminary mechanism study
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A simple and efficient bromination of aniline, aniline derivatives, and analogs have been developed. Forty three examples were given and the highest yield reached was 98%. Different substrates including substituted aniline, pyridin-amine, N-substituted aniline, N,N-disubstituted aniline, N-phenyl-amide, N-phenyl-sulfonamide, and nitrogen-containing heterocycles were all reactive and selectively generated desired bromo-products. The method can be applied to synthesize drug intermediate and quinoxaline derivatives.
- Zhao, Hong-Yi,Yang, Xue-Yan,Lei, Hao,Xin, Minhang,Zhang, San-Qi
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supporting information
p. 1406 - 1415
(2019/05/01)
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- Modulating absorption and charge transfer in bodipy-carbazole donor-acceptor dyads through molecular design
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Three bodipy-based (BDP = 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) donor-acceptor dyads were designed and synthesized, and their ground-state and photophysical properties were systematically characterized. The electronic coupling between the BDP chromophore and an electron-donating carbazole (Carb) moiety was tuned by attachment via the meso and the beta positions on the BDP core, and through the use of various chemical linkers (phenyl and alkynyl) to afford mesoBDP-Carb, mesoBDP-phen-Carb, and betaBDP-alk-Carb. meso-Substituted dyads were found to retain ground-state absorption features of the unsubstituted BDP. However, variation of the linkage between the donor and acceptor moieties modulated the photophysical behavior of excited-state deactivation by controlling the rate of photoinduced internal charge transfer (ICT). The beta-substituted dyad dramatically tuned (red shifted) the absorption spectrum, while retaining desired features of the BDP, specifically stability and high extinction coefficients, however the ICT kinetics were accelerated compared to the meso-substituted dyads. Density functional theory (DFT) and time-dependent DFT (TDDFT) were carried out on the six potential dyads formed between BDP and Carb (attachment using the beta and meso positions for all three connections: direct, phenyl and alkynyl) to support the experimental observations. DFT and TDDFT showed molecular orbital density spread across the HOMO level only when attachment occurred through the beta position of BDP. In the meso-substituted BDP-Carb dyads, the molecular orbitals resembled those of the unsubstituted BDP. This work reveals several possible synthetic paradigms to tune photophysical properties with directed synthetic modifications and provides a mechanistic understanding of the ground- and excited- state behavior in these small-molecule donor-acceptor dyads.
- Strahan, John,Popere, Bhooshan C.,Khomein, Piyachai,Pointer, Craig A.,Martin, Shea M.,Oldacre, Amanda N.,Thayumanavan,Young, Elizabeth R.
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supporting information
p. 8488 - 8501
(2019/06/18)
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- Hydride-catalyzed selectively reductive cleavage of unactivated tertiary amides using hydrosilane
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The first hydride-catalyzed reductive cleavage of various unactivated tertiary amides, including the biologically active aryl-phenazine carboxamides and the challenging non-heterocyclic carbonyl functions, using low-cost hydrosilane as a reducing reagent has been developed. The novel catalyst system exhibits high efficiency and exclusive selectivity, providing the desired amines in useful to excellent yields under mild conditions. Overall, this transition metal-free process may offer a versatile alternative to currently employed expensive reducing reagents, high-pressure hydrogen or metal systems for the selective reductive cleavage of amides.
- Yao, Wubing,Li, Rongrong,Yang, Jianguo,Hao, Feiyue
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p. 3874 - 3878
(2019/08/07)
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- Asymmetric oxidative coupling of hydroxycarbazoles: Facile synthesis of (+)-bi-2-hydroxy-3-methylcarbazole
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Asymmetric oxidative coupling reactions of hydroxycarbazoles have been established using a chiral dinuclear vanadium complex. To demonstrate the utility of vanadium-catalyzed reactions, we have used them to synthesize (+)-bi-2-hydroxy-3-carbazole in three steps from cyclohexanone and commercially available aniline derivatives.
- Sako, Makoto,Sugizaki, Akimasa,Takizawa, Shinobu
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supporting information
p. 2751 - 2753
(2018/03/05)
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- Atom-Economic Electron Donors for Photobiocatalytic Halogenations
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In vitro cofactor supply and regeneration have been a major obstacle for biocatalytic processes, in particular on a large scale. Peroxidases often suffer from inactivation by their oxidative co-factor. Combining photocatalysis and biocatalysis offers an innovative solution to this problem, but lacks atom economy due to the sacrificial electron donors needed. Herein, we show that redox-active buffers or even water alone can serve as efficient, biocompatible electron sources, when combined with photocatalysis. Mechanistic investigations revealed first insights into the possibilities and limitations of this approach and allowed adjusting the reaction conditions to the specific needs of biocatalytic transformations. Proof-of-concept for the applicability of this photobiocatalytic reaction setup was given by enzymatic halogenations.
- Seel, Catharina Julia,Králík, Antonín,Hacker, Melanie,Frank, Annika,K?nig, Burkhard,Gulder, Tanja
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p. 3960 - 3963
(2018/09/25)
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- Visible-light-promoted intramolecular C-H amination in aqueous solution: Synthesis of carbazoles
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An effective and operationally simple protocol is reported for the synthesis of versatile carbazoles. With water as a co-solvent, visible-light rather than various metals is used to facilitate the conversion of readily available 2-azidobiphenyls under mild conditions. Various functionalized bioactive natural alkaloids, such as glycoborine, clausine C, clausine L, clausine H and clauszoline K, were synthesized efficiently with nitrogen as a sole byproduct. The reaction could be performed in water, acidic or alkaline buffer solutions, showing its potential for applications in biochemistry.
- Yang, Lizheng,Zhang, Yipin,Zou, Xiaodong,Lu, Hongjian,Li, Guigen
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supporting information
p. 1362 - 1366
(2018/03/26)
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- Copper(II) catalyzed aromatization of tetrahydrocarbazole: An unprecedented protocol and its utility towards the synthesis of carbazole alkaloids
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An efficient protocol for the aromatization of tetrahydrocarbazole is described by using catalytic copper(II) chloride dihydrate in DMSO. This newly established methodology has utilized towards the synthesis of naturally occurring carbazole alkaloids, namely 3-methylcarbazole, 3-formyl carbazole, glycozoline, glycozolicine and clauszoline-K. In addition, the protocol is generalized for the aromatization of N-substituted tetrahydrocarbazole, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline and 1,2,3,4-tetrahydro β-carboline to give the corresponding heteroaromatic compounds from very good to excellent yield. Moreover, this method has been proven to be tolerant to a broad range of functional groups with excellent yields.
- Dalvi, Bhakti A.,Lokhande, Pradeep D.
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supporting information
p. 2145 - 2149
(2018/05/08)
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- A copolymer containing imidazole salt ion iridium complex and its preparation and use (by machine translation)
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The invention relates to a preparation method and an application of an ion type iridium complex containing imidazolium salt. The iridium complex comprises a cyclometalated ligand and an auxiliary ligand with an active nitrogen-hydrogen structure. The imidazolium salt ion type iridium complex has excellent luminescence property and high color purity, and can realize the regulation from red light to blue-green light by changing counter ions or under the electric field stimulating action. The iridium complex can be applied to sensors and electroluminescence devices.
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Paragraph 0032; 0033; 0034; 0035
(2017/08/26)
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- LIGHT EMITTING ELECTROCHEMICAL CELLS AND COMPOUNDS
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Charged organic thermally activated delayed fluorescence (TADF) species are described. A light-emitting electrochemical cell (LEEC) includes the charged organic thermally activated delayed fluorescence (TADF) species and sufficient counter ions to balance the charge on the charged organic thermally activated delayed fluorescence species, as emitter material. Also disclosed are OLEDSs containing the TADF species.
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Paragraph 0133; 0134
(2018/01/09)
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- NOVEL ORGANIC COMPOUND, MATERIAL COMPRISING THE SAME FOR ORGANIC ELECTROLUMINESCENCE DEVICES, AND ORGANIC ELECTROLUMINESCENCE DEVICE COMPRISING THE MATERIAL
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The present invention provides a novel organic compound, a material comprising the same for organic electroluminescence devices, and an organic electroluminescence device comprising the material. The organic compound provided in the present invention is useful in organic electroluminescence devices as a hole injection layer material, a hole transport layer material, an electron blocking layer material, and an emission layer material such as green and red phosphorescent host material, and can reduce the drive voltage, and increase the luminous efficiency, luminance, thermal stability, color purity and service life of the devices.
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- NOVEL ORGANIC COMPOUND, MATERIAL COMPRISING THE SAME FOR ORGANIC ELECTROLUMINESCENCE DEVICES, AND ORGANIC ELECTROLUMINESCENCE DEVICE COMPRISING THE MATERIAL
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The present invention provides a novel organic compound of General Formula 1, a material comprising the same for organic electroluminescence devices, and an organic electroluminescence device comprising the material. The organic compound of the present invention is useful in organic electroluminescence devices as a hole injection layer substance, a hole transport layer substance, an electron blocking layer substance, and an emission layer substance such as green and red phosphorescent host substance, and when used in the organic electroluminescence devices, can reduce the drive voltage, and increase the luminous efficiency, luminance, thermal stability, color purity and service life of the devices.
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- Synthesis of novel styryl-: N -isopropyl-9 H -carbazoles for designing trans -conjugated regular silicon hybrid materials
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An efficient synthesis and characterization of several new, conjugated styryl-carbazole compounds functionalized by monovinylsilanes in a stereocontrolled approach is presented. All N-organic derivatives were successfully examined in silylative coupling in the presence of ruthenium-hydride complexes 4 and 5. Furthermore, a novel class of vinylene-arylene linear oligomeric materials with 1,4-bis(dimethylvinylsilyl)naphthalene in the main chain was produced. Both reactions proceed very effectively, stereo- and regioselectively, allowing one to obtain E-isomer derivatives with high isolation yields.
- Majchrzak, Mariusz,Grzelak, Magdalena,Marciniec, Bogdan
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supporting information
p. 9406 - 9415
(2016/10/13)
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- nitrogen-containing polycyclic compound and an organic electroluminescent device including the same
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Disclosed are a nitrogen-containing polycyclic compound and an organic electroluminescent device including the same.
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Paragraph 0288; 0289; 0290
(2016/10/09)
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- Novel 2,1,3-benzothiadiazole derivatives used as selective fluorescent and colorimetric sensors for fluoride ion
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Two novel 2,1,3-benzothiadiazole derivatives, used as colorimetric and fluorescent sensors for fluoride ion were designed, synthesized and characterized. These sensors contained single hydrogen-bond functional groups, which acted as interacting sites for fluoride ion. Both sensors displayed a red color in dimethyl sulfoxide solution. Binding studies revealed that they showed noticeable colorimetric and fluorescent responses only to F- among the eight anions tested (F-, Cl-, Br-, I-, AcO-, H2PO4-, HSO4- and NO3-). 1H NMR titration proved that the interaction between compounds and fluoride ion: hydrogen bond at low fluoride ion concentration, deprotonation at high fluoride ion concentration. Moreover, those compounds showed high sensitivity and selectivity for fluoride ion by inhibiting the excited state intramolecular proton transfer processes, and the detective processes could be followed by direct visual observation.
- Wu, Jiefei,Lai, Guoqiao,Li, Zhifang,Lu, Yunxiang,Leng, Taohua,Shen, Yongjia,Wang, Chengyun
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p. 268 - 276
(2015/10/28)
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- CARBAZOLE-BASED GUMBOS FOR HIGHLY EFFICIENT BLUE OLEDS
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Various examples are provided for carbazole-based GUMBOS (group of uniform materials based on organic salts), and its application in organic light emitting diodes (OLEDs). In one example, a composition includes a solid phase carbazole-based GUMBOS (group of uniform materials based on organic salts) comprising a counterion such as, e.g., trifluoromethanesulfonate ([OTf]), bis-(trifluoromethanesulfonyl)imide ([NTf2]), bis-(pentafluoroethylsulfonyl)imide ([BETI]), tetrafluoroborate (BF4), hexafluorophosphate (PF6), and/or thiocyanate (SCN). The carbazole-based GUMBOS can include carbazoleimidazole-based GUMBOS or 3,6-diBDC carbazolium-based GUMBOS. In another example, a method includes preparing a biphasic solution; separating a layer of DCM from the biphasic solution after stirring; washing the DCM with water to remove byproducts; and evaporating the DCM to form a solid phase carbazoleimidazole-based GUMBOS. Preparing the biphasic solution can include carbazoleimidazolium iodide (CM) dissolved in dichloromethane (DCM) and a dissolved salt including a sodium salt or a lithium salt.
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Paragraph 0100
(2016/08/17)
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- Conjugated aralkynyl carbazole compound
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The invention discloses a conjugated aralkynyl carbazole compound. The conjugated aralkynyl carbazole compound is characterized in that a benzene ring is the center of the compound and a basin-shaped molecule is formed by symmetric substitution of the position 1 and position 4 of the benzene ring with carbazole groups containing aralkynyl groups. The compound is prepared by subjecting halogenated ferrocenium salt to a nucleophilic substitution reaction and then carrying out a photolysis reaction; so the compound is simple to prepare. The conjugated aralkynyl carbazole compound has high fluorescence quantum yield and strong two-photon absorption performance and can be applied to two-photon absorption materials like two-photon fluorescence probe compounds and optical information recording mediums.
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Paragraph 0019
(2017/01/17)
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- FUNCTIONALISED AND SUBSTITUTED CARBAZOLES AS ANTI-CANCER AGENTS
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The present invention relates to anti-tropomyosin compounds, processes for their preparation, and methods for treating or preventing a disease or disorder, such as a proliferative disease (preferably cancer), using compounds of the invention.
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Page/Page column 40; 41
(2016/02/26)
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- One kind has electronic to the receptor structure of vinyl polymer main body material and its preparation and application method (by machine translation)
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The invention belongs to the field of photoelectric functional materials, in particular to a kind of by the electron donor group with the electron acceptor group are respectively functional modification of the PVK vinyl polymer main body material, and based on this polymer a series of optical, electrical, electrochemical performance characterization, we would be applied to the organic light-emitting field, has been succeeded in preparing a series of high-efficiency light-emitting device. Wherein the polymer material of the main body and PTPACzPO PVPPOK as an example, their traditional hole transporting material (polyvinyl carbazole) PVK as the skeleton, through a series of molecular modification, to obtain a more superior to the PVK carrier transmission performance. (by machine translation)
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Paragraph 0065; 0066; 0067
(2017/01/02)
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- For organic electroluminescence device compounds and organic electroluminescent device
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The invention provides a compound used on an organic electroluminescent device and the organic electroluminescent device. The component is of a structure represented by formula (1). An X and a Y are groups which are selectively composed of carbazole which is replaced by independent alkyl or aryl, or not replaced and is represented by free formula (A), (B), (C), (D), or (E), benzpyrole carbazole, triphenylsily, diphenyl phosphine oxide. An RI, an R2 and an R3 are groups which are selectively composed of free hydrogen, alkyl with one to fifteen carbon, aryl with six to fifteen carbon, triphenylsily which is replaced by alkyl or aryl, or not replaced and is represented by formula (D) or (E) replaced and diphenyl phosphine oxide. M and n are independently to be zero or one, wherein a limiting condition is that the sum of m and n is equal to or larger than one. And Ar1 and Ar2 are groups which are selectively composed of phenyl which is replaced by independent alkyl or aryl, or not replaced, tolyl, naphthyl, fluorenyl, anthryl, and phenathryl.
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Paragraph 0184-0185
(2016/10/08)
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- HETERO-CYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME
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The present invention provides: a heterocyclic compound capable of greatly improving lifespan, efficiency, electrochemical stability and thermal stability of an organic light emitting device; and an organic light emitting device where the heterocyclic compound is contained in an organic compound layer. In addition, the heterocyclic compound is represented by chemical formula 1.COPYRIGHT KIPO 2016
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Paragraph 0157; 0158; 0159
(2016/10/09)
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- Novel metal-free organic dyes possessing fused heterocyclic structural motifs for efficient molecular photovoltaics
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Reported herein are six novel metal free organic dyes such as PCA1-PCA3 and PCTA1-PCTA3 featuring fused heterocyclic structural motifs such as phenothiazine and alkylcarbazole. Photophysical/electrochemical properties and nanocrystalline TiO2 based dye-sensitized solar cell performance of the same have been investigated. Electronic distribution within the molecules has been determined through a computational approach. The overall power conversion efficiencies of the devices with the utilization of dyes PCA1-PCA3 and PCTA1-PCTA3 as sensitizers ranges between 4.67 and 8.08%. The novel dyes possessing cyanoacrylic acid as electron acceptor, PCA1-PCA3, exhibit higher power conversion efficiency, short-circuit current, open-circuit voltage, and electron lifetime those with thioxothiazolidinylacetic acid, PCTA1-PCTA3, as the same. Of the devices fabricated by employing the new metal-free organic sensitizers, that with the dye PCA2 exerted a power conversion efficiency (PCE, η) of 8.08% with a short circuit current density (JSC) of 16.45 mA cm-2, an open circuit voltage (VOC) of 735 mV and a fill factor (ff) of 0.68; this PCE is the highest amongst the devices fabricated.
- Karuppasamy, Ayyanar,Stalindurai, Kesavan,Peng, Jia-De,Ho, Kuo-Chuan,Ramalingan, Chennan
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p. 30105 - 30116
(2016/11/17)
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
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The present invention provides: a compound; an organic electric element using the same; and an electronic device thereof. The compound is represented by chemical formula 1, and has cross-linking properties by comprising one or more cross-linking forming groups represented by at least one of R^1, R^2, and Ar^1 to Ar^3. According to the present invention, the organic electric element using the compound has high light-emitting efficiency, low driving voltage, and improved lifespan.(110) Substrate(120) Positive electrode(130) Hole injection layer(140) Hole transport layer(141) Buffer layer(150) Light emitting layer(151) Light-emitting assisting layer(160) Electron transport layer(170) Electron injection layer(180) Negative electrodeCOPYRIGHT KIPO 2016
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Paragraph 0206-0211; 0215-0219; 0222; 0223; 0243-0246; 0249
(2016/10/07)
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- Structure-properties relationship of the derivatives of carbazole and 1,8-naphthalimide: Effects of the substitution and the linking topology
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Nine compounds having electron-accepting 1,8-naphthalimide and electron-donating carbazole moieties were synthesized employing palladium-catalyzed C-N and C-C coupling reactions and characterized by the thermal methods, absorption and emission spectrometry, electrochemical and photoelectrical tools. The synthesized compounds possess high thermal stability with the 5% weight loss temperatures being in the range of 351-476 °C. Most of the synthesized compounds are capable of glass formation with glass transition temperatures ranging from 30 to 87 °C. The cyclic voltammetry measurements showed that the solid state ionization potentials values of the carbazole and 1,8-naphthalimide derivatives range from 5.46 eV to 5.76 eV and the electron affinities values range from -3.04 eV to -2.92 eV. Dilute solutions of the 3- and 3,6-naphthalimide-substituted derivatives of carbazole in polar solvents were found to emit in the green region with quantum yields ranging from 0.66 to 0.83, while in the solid state fluorescence quantum yields were found to be in the range of 0.01-0.45. ((E)-9-(((N-(2-ethylhexyl)-1,8-naphthalimide)-4-yl)ethenyl)-9H-carbazole) exhibited efficient fluorescence in the solid state with quantum yield as high as 0.45. The effects of the linking topology of the chromophores and of the incorporated alkyl substituents on the thermal, optical, and photoelectrical properties of the synthesized donor-acceptor compounds are analyzed. The impact of the ground state intramolecular twisting of the carbazole and naphthalimide moieties induced by the substituents resulting in significant variation in the rates of radiative and nonradiative excitation deactivation is revealed.
- Gudeika, Dalius,Grazulevicius, Juozas Vidas,Volyniuk, Dmytro,Butkute, Rita,Juska, Gytis,Miasojedovas, Arunas,Gruodis, Alytis,Jursenas, Saulius
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p. 239 - 252
(2015/03/31)
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
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Provided in the present invention are a novel compound which can improve light emitting efficiency, stability, and life, an organic electronic element using the same, and an electronic device thereof. The organic electronic element is characterized by comprising a first electrode; a second electrode; and an organic substance layer located between the first electrode and the second electrode, wherein the compound is contained in the organic substance layer. The organic electronic element is characterized by having the compound contained in at least one layer among a hole injection layer, a hole transfer layer, an light emitting auxiliary layer, or a light emitting layer of an organic substance layer.(140) Hole transfer layer(141) Buffer layer(150) Light emitting layer(151) Auxiliary light emitting layer(160) Electron transfer layer(170) Electron injection layer(180) Negative electrode(130) Hole injection layer(120) Positive electrode(110) SubstrateCOPYRIGHT KIPO 2015
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Paragraph 0226; 0227; 0228
(2016/10/08)
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
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The present invention provides a novel compound to improve light emission efficiency and stability of an element and to extend lifespan of the element, an organic electronic element using the same, and an electronic device thereof. The compound is represented by chemical formula 1, wherein m is a constant in the range of zero and four, and n is a constant in the range of zero and three.(140) Hole transfer layer(141) Buffer layer(150) Light emitting layer(151) Light-emitting assisting layer(160) Electron transfer layer(170) Electron injection layer(180) Negative electrode(130) Hole injection layer(120) Positive electrode(110) SubstrateCOPYRIGHT KIPO 2015
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- COMPOUND FOR ORGANIC ELECTRIC ELEMENT, ORGANIC ELECTRIC ELEMENT COMPRISING THE SAME AND ELECTRONIC DEVICE THEREOF
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The present invention provides a compound represented by Chemical Formula 1. Moreover, provided is an organic electric element including a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode, wherein the organic material layer includes the compound represented by Chemical Formula 1. When the compound represented by Chemical Formula 1 is included in the organic material layer of the organic electric element, a driving voltage is reduced, and light emitting efficiency, color purity, and lifecycle may be improved.(110) Substrate(120) Positive electrode(130) Hole injecting layer(140) Hole transporting layer(141) Buffer layer(150) Light-emitting layer(151) Light-emitting assisting layer(160) Electron transferring layer(170) Electron injecting layer(180) Negative electrodeCOPYRIGHT KIPO 2015
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