1592-95-6Relevant articles and documents
Vascular barrier protective effects of 3-N- or 3-O-cinnamoyl carbazole derivatives
Ku, Sae-Kwang,Lee, Jee-Hyun,Yuseok,Lee, Wonhwa,Song, Gyu-Yong,Bae, Jong-Sup
, p. 4304 - 4307 (2015)
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.
Multichromophore Molecular Design for Thermally Activated Delayed-Fluorescence Emitters with Near-Unity Photoluminescence Quantum Yields
Chen, Dongyang,Kusakabe, Yu,Ren, Yongxia,Sun, Dianming,Rajamalli, Pachaiyappan,Wada, Yoshimasa,Suzuki, Katsuaki,Kaji, Hironori,Zysman-Colman, Eli
, p. 11531 - 11544 (2021)
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%.
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
Park, Jun Ha,Yun, Changhun,Koh, Tae-Wook,Do, Youngkyu,Yoo, Seunghyup,Lee, Min Hyung
, p. 5422 - 5429 (2011)
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.
Comparison of Carbazole and Fluorene Donating Effects on the Two-Photon Absorption and Nitric Oxide Photorelease Capabilities of a Ruthenium–Nitrosyl Complex
Enriquez-Cabrera, Alejandro,Lacroix, Pascal G.,Sasaki, Isabelle,Mallet-Ladeira, Sonia,Farfán, Norberto,Barba-Barba, Rodrigo M.,Ramos-Ortiz, Gabriel,Malfant, Isabelle
, p. 531 - 543 (2018)
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.
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
Zhou, Jun,Yu, Xiaoguang,Jin, Xueliang,Tang, Guipeng,Zhang, Wei,Hu, Jiaomei,Zhong, Chaofan
, p. 14 - 21 (2014)
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).
An Upgraded “Two-in-One” Strategy toward Highly Crystalline Covalent Organic Frameworks
Chen, Dan,Chen, Weiben,Xing, Guolong,Zhang, Ting,Chen, Long
, p. 8377 - 8381 (2020)
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.
Carbazole-based two-photon fluorescent probe for selective imaging of mitochondrial hydrogen peroxide in living cells and tissues
Zhang, Kai,Wu, Wei,Li, Yinhui,Sun, Mingtai,Yu, Huan,Wong, Man Shing
, p. 115298 - 115302 (2016)
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.
Nine-ring angular fused biscarbazoloanthracene displaying a solid state based excimer emission suitable for OLED application
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.
, p. 5795 - 5805 (2016)
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.
Fluorescent pyrene-centered starburst oligocarbazoles with excellent thermal and electrochemical stabilities
Ren, Ming-Guang,Guo, Hui-Jun,Qi, Fei,Song, Qin-Hua
, p. 6913 - 6916 (2011)
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.
Bipolar iridium dendrimers containing carbazolyl dendron and 1,2,4-triazole unit for solution-processed saturated red electrophosphorescence
Liang, Bo,Hu, Sujun,Liu, Yanping,Fan, Zhiqiang,Wang, Xueye,Zhu, Weiguo,Wu, Hongbin,Cao, Yong
, p. 41 - 51 (2013)
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.
Determination and reduction of translocator protein (TSPO) ligand rs6971 discrimination
Sokias, Renee,Werry, Eryn L.,Chua, Sook W.,Reekie, Tristan A.,Munoz, Lenka,Wong, Erick C. N.,Ittner, Lars M.,Kassiou, Michael
, p. 202 - 210 (2017)
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.
Functionalization of biphenylcarbazole (CBP) with siloxane-hybrid chains for solvent-free liquid materials
Correia, Gabriel,Heinrich, Beno?t,Méry, Stéphane,Mager, Lo?c,Polychronopoulou, Kyriaki,Ribierre, Jean-Charles,Shaya, Janah
, (2021/12/29)
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.
Preparation method of 3 - bromo - N - phenyl carbazole
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Paragraph 0024; 0030-0031; 0039; 0045-0046, (2021/10/11)
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.
