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.
Ruthenium catalyzed remote C4-selective C-H functionalisation of carbazoles: Via σ-activation
Leitch, Jamie A.,Heron, Callum J.,McKnight, Janette,Kociok-K?hn, Gabriele,Bhonoah, Yunas,Frost, Christopher G.
, p. 13039 - 13042 (2017)
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.
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%.
Thermally cross-linkable thermally activated delayed fluorescent materials for efficient blue solution-processed organic light-emitting diodes
Sun, Kaiyong,Xie, Xiafei,Liu, Yao,Jiang, Wei,Ban, Xinxin,Huang, Bin,Sun, Yueming
, p. 8973 - 8979 (2016)
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.
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.
Simultaneous discrimination of diameter, handedness, and metallicity of single-walled carbon nanotubes with chiral diporphyrin nanocalipers
Liu, Gang,Wang, Feng,Chaunchaiyakul, Songpol,Saito, Yukie,Bauri, Ajoy K.,Kimura, Takahide,Kuwahara, Yuji,Komatsu, Naoki
, p. 4805 - 4814 (2013)
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.
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).
Carbazole-based D-π-A molecules: Determining the photophysical properties and comparing ICT effects of π-spacer and acceptor groups
Altinolcek, Nuray,Battal, Ahmet,Vardalli, Cemre Nur,Tavasli, Mustafa,Yu, Holly A.,Peveler, William J.,Skabara, Peter J.
, (2021)
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.
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.
