- Synthesis, Structure and Magnetic Property of a Cobalt(II) Metal-Organic Framework
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The three-dimensional (3D) porous cobalt(II) metal-organic framework (MOF), [Co3(L)2(DMA)2(MeOH)2·4(DMA)·6(MeOH)]n (1) [L = fully deprotonated 2,7-bis(4-benzoic acid)-N-(4-benzoic acid) carbazole, DMA = N,N-dimethylacetamide], was synthesized by hydrothermal reaction. Based on X-ray single-crystal diffraction, structural analysis indicates that complex 1 crystallizes in the monoclinic C2/c space group. Complex 1 possesses a 3,6-connected three-dimensional (3D) topological structure with a point symbol of {42·6}2{44·62·87·102} when a trinuclear CoII cluster was regarded as 6-connected node and the organic ligands could be regarded as 3-connected linkers between the 6-connected nodes. The framework structure exhibits a one-dimension (1D) channel with an accessible void of 4223.0 ?3, amounting to 42.8 % of the total unit-cell volume (9862.0 ?3). Moreover, the magnetic properties of complex 1 were studied.
- Chen, Dong-Hui,Sheng, Tian-Lu,Zhu, Xiao-Quan,Lin, Ling,Wen, Yue-Hong,Hu, Sheng-Min,Fu, Rui-Biao,Wu, Xin-Tao
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- Thieno[3,4-b]pyrazine-based low bandgap photovoltaic copolymers: Turning the properties by different aza-heteroaromatic donors
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A new series of low-bandgap copolymers based on electron-accepting thieno[3,4-b]pyrazine (TPZ) and different electron-donating aza-heteroaromatic units, such as carbazole (CZ), dithieno[3,2-b:2′,3′-d]pyrrole (TPR) and dithieno[3,2-b:2′,3′-e]pyridine (TPY), have been synthesized by Suzuki or Stille coupling polymerization. The resulting copolymers were characterized by NMR, elemental analysis, gel permeation chromatography, thermogravimetric analysis, and differential scanning calorimetry. UV-vis absorption and cyclic voltammetry measurements show that TPZ-based copolymer with TPR has the best absorption due to the strongest intramolecular charge transfer effect and smallest bandgap. The basic electronic structure of D-A model compounds of these copolymers were also studied by density functional theory (DFT) calculations. The conclusion of calculation agreed also well with the experimental results. The polymer solar cells (PSCs) based on these copolymers were fabricated with a typical structure of ITO/PEDOT:PSS/copolymer: PC71BM/Ca/Al under the illumination of AM 1.5G, 100 mW cm -2. The performance results showed that TPZ-based copolymer with TPR donor segments showed highest efficiency of 1.55% due to enhanced short-circuit current density. The present results indicate that good electronic, optical, and photovoltaic properties of TPZ-based copolymers can be achieved by just fine-tuning the structures of aza-heteroaromatic donor segments for their application in PSCs.
- Peng, Qiang,Liu, Xiangju,Qin, Yuancheng,Zhou, Dan,Xu, Jun
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- Efficient Synthesis of 2,7-Dibromocarbazoles as Components for Electroactive Materials
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An efficient two-step synthesis of 2,7-dibromocarbazole is reported. Nitration and Friedel-Crafts acylation of 2,7-dibromocarbazole proceed readily at the activated 3 and 6 positions to give new multifunctionalised carbazoles, which are of interest as monomers for new electrically active organic materials.
- Dierschke, Frank,Grimsdale, Andrew C.,Muellen, Klaus
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- Dynamically controllable emission of polymer nanofibers: Electrofluorescence chromism and polarized emission of polycarbazole derivatives
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Electrochemical polymerization of a series of N-alkyl-2,7-di(2-thienyl) carbazoles in acetonitrile was performed to obtain conjugated polymers with fluorescence. Scanning electron and atomic force microscopies revealed that the surface morphology of the polymer films significantly depends on the alkyl chain lengths of the polymers. Particularly, a homopolymer bearing hexyl groups and copolymers with an average alkyl chain length of six carbon atoms show nanofiber morphology. The polymer nanofibers were stacked on a substrate electrode. The fluorescence of the polymer nanofiber film was tunable with application of voltage, with good repeatability. The X-ray diffraction pattern of the fibers showed the structural order. The polymer nanofibers thus prepared showed an electrochemically driven change in polarized photoluminescence.
- Kawabata, Kohsuke,Goto, Hiromasa
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- Conjugated polymers with carbazole, fluorene, and ethylene dioxythiophene in the main chain and a pendant cyano group: Synthesis, photophysical, and electrochemical studies
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Six new conjugated polymers comprising of carbazole, fluorene, and ethylene dioxythiophene (EDOT) moieties along the backbone with a pendant cyano group attached to the ethylene moiety have been designed and synthesized via Sonogashira coupling polymerization reaction. Optical and electrochemical characterizations have shown that the energy band gaps lie within the range of 2.35–2.44 eV. Additionally, the presence of carbazole and EDOT makes these polymers better hole transporting materials, which is reflected from their low oxidation potential peaks (0.55–1.11 V) in cyclic voltammograms. Furthermore, the aggregation enhanced emission (AEE) phenomenon resulted in a 2.6-fold increase in fluorescence intensity in a 90:10 THF/water mixture in comparison to pristine THF. The AEE properties were further verified by DLS (dynamic light scattering) experiment and SEM (scanning electron microscopy) studies. Polymers in solution as well as in polystyrene matrix emit in the green region (quantum yield in solution state Φf =41–43%) with CIE values (0.25–0.36, 0.52–0.57). Excellent thermal stability is observed for the new polymers.
- Anand, Vivek,Ramachandran, Elumalai,Dhamodharan, Raghavachari
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- Syntheses, structures and luminescence properties of five coordination polymers based on designed 2,7-bis(4-benzoic acid)-: N -(4-benzoic acid) carbazole
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Herein we report five porous luminescent coordination polymers (CPs), namely, [Zn3(L27)2(DMA)6(H2O)4]n (TCZ-001), [Zn3(L27)2(DMA)6(CH3CH2OH)2]n (TCZ-002), [Zn3(L27)2(DMA)6(CH3OH)]n (TCZ-003), [Cd3(L27)2(DMA)6(H2O)2]n (TCZ-004), and [Cd9(L27)6DMA13(4,4′-BPY)2(OH)2(H2O)13.5]n (TCZ-005) [H3L27 = 2,7-bis(4-benzoic acid)-N-(4-benzoic acid) carbazole, DMA = N,N-dimethylacetamide, 4,4′-BPY = 4,4′-bipyridine, TCZ = "T"-shape carbazole-based polymers, L27 = fully deprotonated H3L273- ligand]. All of the five CPs were assembled from a novel luminescent carbazole-based ligand. X-ray crystallography showed that TCZ-001 is a 3-connected one-dimensional (1D) chain structure with a {42·6} topology. TCZ-002 possesses a 3,6-connected three-dimensional (3D) framework with a point symbol of {42·6}2{44·62·87·102}. TCZ-003 displays a 3,6-connected two-dimensional 2D network with a Schl?fli symbol of {411·64}·{43}2, which is a new topology. TCZ-004 features a 3,6-connected 2D net with a {43}2·{46·66·83} topology. In TCZ-005, the structure can be classified into two groups: one of the two groups is a 3-connected 1D chain structure with a {42·6} topology, similar to TCZ-001; the other one possesses a 3,3,3,4-connected network with a Schl?fli symbol of {42·63·8}{42·6}3. The structure of TCZ-005 could be described as an SP 1-periodic net (4,4)(0,2) in the 1D-2D.ttd database. TCZ-001, TCZ-003 and TCZ-004 show a remarkable response to the Ni2+ concentration in DMA, H2O or EtOH. Some of Zn2+ ions were replaced by Ni2+ ions and the rate of the transmetalation depended on the concentration of Ni2+ ions. Also, changing part of the metal node would transform the colour of emitted light. Additionally, the colour of the luminescence displays a linear correlation with the Ni2+ concentration range from 0.005 to 0.35 M (mol L-1). Besides selective sensing of Ni2+, TCZ-004 can also be utilized to detect Eu3+ in DMA solution. Thus, several potential sensory probe materials for Ni2+ and Eu3+ detection in DMA solution have been obtained.
- Chen, Dong-Hui,Lin, Ling,Sheng, Tian-Lu,Wen, Yue-Hong,Hu, Sheng-Min,Fu, Rui-Biao,Zhuo, Chao,Li, Hao-Ran,Wu, Xin-Tao
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- Simple synthesis and molecular engineering of low-cost and star-shaped carbazole-based hole transporting materials for highly efficient perovskite solar cells
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Perovskite solar cells (PrSCs) have emerged as a very promising technology in the field of photovoltaics by demonstrating power conversion efficiencies (PCEs) soaring from 3.9% to above 22% within the past eight years. To date, perovskite solar cells mainly depend on spiro-OMeTAD to perform a key role as a hole transporting material (HTM). However, the complicated multi-step synthetic procedures and high-cost purification process for spiro-OMeTAD limited its potential for commercial application. Herein, three new carbazole-based HTMs with a starburst structure, coded as SGT-405(3,6), SGT-410(3,6) and SGT-411(3,6) via tuning the substitution position from the (2,7) to the (3,6) position of the carbazole moiety, have been successfully synthesized via three-step synthesis from commercially available reagents and investigated for highly efficient perovskite solar cells. By adopting this strategy, among them, molecularly engineered carbazole derivative SGT-405(3,6) exhibits significantly increased Tg (192.7 °C), improved film forming ability, reduced hole reorganization energy and enhanced hole mobility compared to its parent molecule SGT-405(2,7) and spiro-OMeTAD. Owing to the promising properties of SGT-405(3,6), meso-porous type PrSCs employing SGT-405(3,6) showed a remarkable PCE of 18.87%, which is better than that of the photovoltaic device employing spiro-OMeTAD (17.71%). To the best of our knowledge, the achieved PCE (18.87%) is the highest value reported for devices with the structure of FTO/compact TiO2/meso-porous TiO2/CH3NH3PbI3-xClx/HTM/Au employing small-molecular HTMs. Meanwhile, owing to the simple synthesis of SGT-405(3,6), compared with SGT-405(2,7) previously developed by our group, synthesis cost was much lowered, resulting in low cost compared to the spiro-OMeTAD and SGT-405(3,6), by approximately three times. Furthermore, the long-term device stability of PrSCs was enhanced for SGT-405(3,6) to some extent compared to those of other HTMs studied here due to the good uniform capping layer of SGT-405(3,6) on top of the perovskite layer and the prevention of moisture penetration into the perovskite layer. Therefore, SGT-405(3,6) is a promising low-cost and efficient non-spiro type HTM with potential to replace expensive spiro-OMeTAD for PrSCs.
- Lu, Chunyuan,Choi, In Taek,Kim, Jeongho,Kim, Hwan Kyu
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- Two-photon fluorescent probe for detecting cell membranal liquid-ordered phase by an aggregate fluorescence method
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The cell membranal liquid-ordered (Lo) phase can control the structure and function of cell membranes. In this study, we have engineered a novel two-photon (TP) fluorescent probe, TP-HVC18, which remarkably displayed two different fluorescence emission profiles in the aggregate and solution states in distinct polar environments. In accordance with its aggregate fluorescence, TP-HVC18 also can emit a red fluorescence signal in Lo phase vesicles. Taking advantage of this unique feature, we have demonstrated that the new TP probe TP-HVC18 is suitable for imaging membranal Lo phase by an aggregate fluorescence method. Furthermore, the robust probe also exhibited uncontinuous red fluorescence distribution in the cell membranal Lo phase. Based on this intriguing character, we also successfully showed that the novel probe can be employed to exhibit uncontinuous distribution of cell membranal Lo phase by a 3D imaging technique. We expect that this aggregation-based fluorescent platform may be extended for the development of a wide variety of TP fluorescent probes for detecting several biological species.
- Liu, Yong,Meng, Fangfang,Nie, Jing,Niu, Jie,Yu, Xiaoqiang,Lin, Weiying
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- Fluorescence behavior of a unique two-photon fluorescent probe in aggregate and solution states and highly sensitive detection of RNA in water solution and living systems
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It is found that 2,7-substituted carbazole derivative HVC-6 possesses distinct luminescence features in both aggregate and solution states. In view of this, probe HVC-6 realizes highly sensitive detection of RNA in pure water systems by an aggregation-disaggregation method for the first time.
- Liu, Yong,Meng, Fangfang,He, Longwei,Yu, Xiaoqiang,Lin, Weiying
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- Synthesis of hyperbranched polythiophenes containing tetrachloroperylene bisimide as bridging moiety for polymer solar cells
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The goal of this research is to synthesize the hyperbranched polythiophene derivatives (P1 and P4) containing tetrachloroperylene bisimide as bridging moiety for investigation of thermal, electrochemical, and opto-electrical properties of these derivatives. The polymers (P2 and P3) containing soft alkyl spacer as bridging moiety and linear poly(3-hexylthiophene) (P3HT) were also synthesized for comparison in this study. Polymers with high regioregularity were synthesized via the Universal Grignard metathesis polymerization. The GPC results showed that molecular weights of hyperbranched polythiophenes are higher than that of P3HT. The TGA experiments revealed a first-stage weight loss at about 300 °C for all polymers; besides, polymers containing rigid tetrachloroperylene bisimide groups possess less weight loss than P3HT after heating, indicative of enhanced thermal stabilities. The UV-vis absorption maxima of hyperbranched polymers are similar to that of P3HT in film state, while their absorption shoulder bands are stronger than that of P3HT, indicating stronger interchain interaction and shorter distance between backbones by the introduction of bridge architecture. Moreover, an attenuation of fluorescent intensity was found for those hyperbranched polymers, implying reduced recombination of excitons to emit light and more opportunity for carriers to migrate to both electrodes. Electrochemical analysis showed that introducing hyperbranched structure resulted in decreasing both LUMO and HOMO levels of polymers. All polymers were used for fabrication of polymer solar cells with the configuration of ITO/PEDOT/polymer:PC60BM (1:2 w/w)/LiF/Al to evaluate their performance. The power conversion efficiency (PCE) of the P3HT:PC60BM-based device is 0.54%, while devices based on hyperbranched polymers showed PCE values in the range of 0.45-0.84%. The morphological study of polymer:PC60BM blend films was performed by AFM for interpretation of efficiency trend of devices.
- Yang, Sheng-Hsiung,Lin, Tz-Shiuan,Huang, Yu-Zhang,Li, Husan-De,Chao, Yu-Chiang
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- Syntheses, structures, luminescence and magnetic properties of seven isomorphous metal-organic frameworks based on 2,7-bis(4-benzoic acid)-: N -(4-benzoic acid)carbazole
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We report herein seven novel lanthanide metal-organic frameworks (Ln-MOFs), [M(L27)(DMA)(H2O)·XH2O]n (TCZ-M), (M = Nd, Sm, Eu, Gd, Tb, Dy, Ho), (X = 2 or 3) (H3L27 = 2,7-bis(4-benzoic acid)-N-(4-benzoic acid)carbazole, DMA = N,N-dimethylacetamide, TCZ = "T"-shape carbazole-based MOFs, L27 = fully deprotonated H3L273- ligand). X-ray crystallography showed that all the TCZ-M (M = Nd, Sm, Eu, Gd, Tb, Dy, Ho) are isomorphous and possess a 3,6-connected three-dimensional (3D) framework with a point symbol of {4·62}2{42·610·83}. The photoluminescence measurement indicates that TCZ-Eu shows reddish-orange emission bands and TCZ-Sm shows both visible and near-infrared (NIR) emission bands. Magnetic susceptibility measurements show deviations from the Curie law mainly owing to the split of the ground term due to the ligand field and spin-orbit coupling in TCZ-Eu and TCZ-Sm. The magnetic properties of TCZ-M (M = Nd, Gd, Tb, Dy, Ho) are also investigated, and the results indicate a ferromagnetic interaction between the Tb3+ magnetic centers in TCZ-Tb and the antiferromagnetic interactions in TCZ-M (M = Nd, Gd, Dy, Ho).
- Chen, Dong-Hui,Lin, Ling,Sheng, Tian-Lu,Wen, Yue-Hong,Zhu, Xiao-Quan,Zhang, Lin-Tao,Hu, Sheng-Min,Fu, Rui-Biao,Wu, Xin-Tao
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- Novel conjugated alternating copolymer based on 2,7-carbazole and 2,1,3-benzoselenadiazole
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A novel conjugated alternating copolymer (PCzDBSe) based on N-9'-heptadecanyl-2,7-carbazole and 5,5-(4',7'-di-2-thienyl-2',1',3'-benzoselenadiazole) was synthesized by Suzuki polycondensation. The polymer reveals excellent thermal stabilities with the decomposition temperature (5% weight loss) of 390°C and the glass-transition temperature of 140°C. The absorption peaks of the polymer are located at 412 and 626nm, respectively, while the absorption onset is extended to 716nm, which is 56nm red-shifted as compared with its analogue, poly[N-9'-heptadecanyl-2,7-carbazole-alt-5,5-(4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)] (PCDTBT). The HOMO and LUMO levels of the polymer were estimated to be -5.28 and -3.55eV, respectively, with an optical bandgap of 1.73eV. The hole mobility of PCzDBSe as deduced from a solution-processed organic field effect transistor (OFET) was found to be 3.9×10-4cm2V-1s-1. Polymer solar cells (PSCs) based on the blends of PCzDBSe and [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) with a weight ratio of 1:4 were fabricated. Under AM 1.5 (AM, air mass), 100mWcm-2 illumination, the devices were found to have an open-circuit (Voc) of 0.75V, a short-circuit current density (Jsc) of 7.23mAcm-2, a fill factor (FF) of 45% and a power conversion efficiency (PCE) of 2.58%. The primary results indicate that 5,5-(4',7'-di-2-thienyl-2',1',3'-benzoselenadiazole) is a promising unit for low bandgap polymer for polymer solar cells.
- Zhao, Wei,Cai, Wanzhu,Xu, Ruixia,Yang, Wei,Gong, Xiong,Wu, Hongbin,Cao, Yong
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- Red organic electroluminescent material and preparation method thereof
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The invention belongs to the technical field of photoelectric display devices, and particularly relates to a red organic electroluminescent material and a preparation method thereof. The invention provides the red light organic electroluminescent material, the structure of which is represented by formula (I): wherein R is a hydrogen atom, a linear chain or branched chain alkyl group with a carbonatom number of 1-20, x is 0-1, and the polymerization degree n is 3-800. The invention also provides a preparation method of the red light organic electroluminescent material. The preparation method comprises that 2', 7 '-dibromo-1, 2, 7, 8-tetraoctyl-9'-spiro-bis[fluorene], 2, 2'-(1', 2 ', 7', 8 '-tetraoctyl-9, 9'-spiro-bis [fluorene]-2, 7-diyl)bis(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborane) and3, 10-dibromo-14-(3-(5-phenyl-1, 3, 4-oxadiazole-2-yl) phenyl)-14H-bis (S, S-dioxo-dibenzothiophene)pyrrole undergo a Suzuki coupling reaction to produce a polymer shown as a formula (I). The red light organic electroluminescent material and the preparation method thereof provided by the invention solve the technical problem of poor electroluminescent performance of the existing red-light polymer.
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Paragraph 0020-0022
(2020/09/16)
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- Multi-photon properties in various condensed phases of dendritic chromophores derived from carbazole and indenoquioxaline units: Synthesis and characterization
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We have used functionalized carbazoles and indenoquonoxalines as the main building units and enthynyl groups as the π-linkages to construct two novel dendritic fluorophores and studied their degenerate multi-photon absorption properties in both the solution phase and the neat-film state within femtosecond and nanosecond regions. In our experiments, these model compounds are found to manifest strong and widely dispersed two-photon absorption as well as effective power-limiting properties against ultra-short laser pulses in the near-IR region. In addition, both chromophores exhibit medium to strong three-photon-induced fluorescence, indicating such scaffold may serve as a reference structural motif for the development of three-photon materials.
- Lin, Tzu-Chau,Chien, Wei,Dai, Shu-Wen,Lin, Hao-Wu,Liu, Yueh-Ching
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p. 140 - 150
(2019/05/01)
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- Double-(S, S - dioxo - dibenzo thiophene) and high output compound and its preparation method and application
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The invention discloses a bi(S,S-dioxo-dibenzothiophene) five-membered ring compound and a preparation method and application thereof. The existence of bi-sulfuryl in the bi(S,S-dioxo-dibenzothiophene) five-membered ring compound is more beneficial for improving the electron affinity of molecules. Alkyl chains are introduced on a five-membered ring, so that the solubility of monomers in an organic solvent can be obviously improved. The plane conjugacy of the compound is better, and is beneficial for the transmission of a current carrier. Higher D-A mutual effect existing in the molecules of the compound endows higher fluorescence of the material. The bi(S,S-dioxo-dibenzothiophene) five-membered ring compound is synthesized and obtained through common organic chemistry reactions such as substitution reactions, Suzuki coupling and ring-closure reactions and oxidation reactions. The compound has good solubility in the organic solvent, and is suitable for solution processing. The compound has wide application prospects in the fields of organic luminescence display, organic photovoltaic cells and organic field-effect tubes.
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Paragraph 0081-0083; 0085
(2019/06/26)
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- KIT FOR DETECTING ctDNA AND EXPRESSION OF DRUG-RESISTANT GENES RELATED TO APPLICABILITY OF TUMOR CHEMOTHERAPEUTIC DRUGS
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A kit for determining ctDNA concentration and a method for determining ctDNA concentration is disclosed, wherein the method comprising dissolving extracted ctDNA in Tris-HCl buffer with pH>7.0 and adding into the buffer 2,7-bis(1-methyl-4-vinylpyridine)-9-ethylcarbazole iodised salt as a molecular probe, calculating the concentration of ctDNA in the solution by measuring the Fluorescence intensity of the solution. It has extremely high sensitivity in the determination of 0 μg/ml?50 μg/ml ctDNA solution.
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Paragraph 0025
(2019/10/23)
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- Compound containing carbazole unit and use thereof
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The invention discloses a compound containing a carbazole unit and a use thereof. The carbazole compound has a structure represented by formula (I): (img file='re-DDA0001591266690000011.TIF' wi='1229'he='1359'/), in the formula (I), R1 is a C1-C12 hydrocarbon group or a C1-C12 alkoxy group or a C4-C20 heterocyclic group, wherein a hetero-atom in the heterocyclic group is N or S or O; R2 is a C1-C12 hydrocarbon group; and R3 and R4 are the same or different aromatic hydrocarbon groups or heterocyclic aromatic hydrocarbon groups. The carbazole compound disclosed by the invention can be used asa hole transport material in perovskite solar cells, organic small molecule solar cells, electroluminescent devices and other photoelectric devices.
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Paragraph 0029; 0030; 0031
(2018/04/28)
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- Two Anthracene-Based Copolymers as the Hole-Transporting Materials for High-Performance Inverted (p-i-n) Perovskite Solar Cells
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Two anthracene-based copolymers, the thiophene-bridged carbazole-anthracene copolymer (abbreviated as PCBZANT) and the thiophene-bridged triphenylamine-anthracene copolymer (abbreviated as PTPAANT), have been developed as the hole-transporting materials (HTMs) for the inverted perovskite solar cells. They were thermally stable with decomposition temperatures of 435 and 420 °C. The High Occupied Molecular Orbitals (HOMO) of -5.15 and -5.24 eV of two copolymers facilitated the hole carriers transfer from the perovskite layer (CH3NH3PbI3, HOMO: -5.4 eV) in contrast to poly(3,4-ethylenedioxythiophene):polystyrenesulfonate (PEDOT:PSS, HOMO: -4.9 eV). The solar cell with PCBZANT (abbreviated as the PCBZANT device) showed the highest power conversion efficiency (PCE) of 15.50%, while the cell with PTPAANT (abbreviated as the PTPAANT device) showed the highest PCE of 14.52%, with increases of 36.2% and 27.6%, respectively, relative to the PEDOT:PSS device. The thorough analysis disclosed that the high performance was mainly ascribed to the enhanced open-circuit voltage (VOC) and short-circuit current density (JSC), being contributed from the efficient hole-carrier extraction, the high hole mobility of two copolymers, and the high-quality perovskite film with large crystal size and less defect. With strong absorption in the range of 350-500 nm, the polymers decreased the destruction of UV-radiation on the perovskite layer as UV-filters and improved the stability of the inverted cells.
- Tong, Tong,Tan, Chao,Keller, Tina,Li, Bobo,Zheng, Chaoyue,Scherf, Ullrich,Gao, Deqing,Huang, Wei
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p. 7407 - 7416
(2018/09/27)
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- Removal of triphenylphosphine oxide by precipitation with zinc chloride in polar solvents
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While the use of triphenylphosphine as a reductant is common in organic synthesis, the resulting triphenylphosphine oxide (TPPO) waste can be difficult to separate from the reaction product. While a number of strategies to precipitate TPPO are available, none have been reported to work in more polar solvents. We report here that mixing ZnCl2 with TPPO precipitates a TPPO?Zn complex in high yield in several common polar organic solvents. The solvent compatibility of this procedure and the reliability of the precipitation in the presence of polar functional groups were examined to show the utility and limitations of this method.
- Batesky, Donald C.,Goldfogel, Matthew J.,Weix, Daniel J.
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p. 9931 - 9936
(2018/05/29)
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- Double-S, S - dioxo - dibenzo thiophene and five-membered ring monomer and its preparation method and polymer
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The invention discloses a bis S,S-dioxo-dibenzothiophene five-membered ring monomer, a preparation method thereof and a polymer. Due to a bis sulfonyl group in the bis S,S-dioxo-dibenzothiophene five-membered ring, the electron affinity of molecules can be improved more easily. By introducing an alkyl chain to the five-membered ring, the solubility of the monomer in organic solvent can be significantly improved, and meanwhile the steric hindrance influence on polymerization reaction from the position of the alkyl chain can be avoided. Due to a large conjugate plane, the cavitation and electron transmission performance of the polymer can be improved. Through Suzuki or Stille or Yamamotor polymerization reaction of the bis S,S-dioxo-dibenzothiophene five-membered ring monomer, a homopolymer or copolymer can be obtained. The polymer of the series has good solubility in organic solvent and is suitable for solution processing. The bis S,S-dioxo-dibenzothiophene five-membered ring monomer has broad application prospects in the fields of organic light-emitting display, organic photovoltaic cells and organic field effect transistors.
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Paragraph 0100; 0102; 0104
(2018/01/11)
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- Carbazole-based π-conjugated polyazomethines: Effects of catenation and comonomer insertion on optoelectronic features
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A series of carbazole-based polyazomethines have been synthesized under micro-wave irradiation and without transition-metal based catalyst. The impact of both the catenation brought by the carbazole subunits and the insertion of a co-monomer, i.e. 3,4 ethylene dioxythiophene (EDOT), on the optical and electrochemical properties have been studied. Among the different polyazomethines synthesized, the best in terms of optical and electrochemical properties has been found to be the one with the azomethine function linked in positions 2,7 of carbazole subunits. Upon the insertion of the EDOT comonomer, an increase of the molecular weight and a red-shift in the absorption spectra has been observed, corresponding to a diminution of the electronic gap.
- Garbay,Muccioli,Pavlopoulou,Hanifa,Hadziioannou,Brochon,Cloutet
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p. 274 - 284
(2017/05/31)
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- Probe for clearly distinguishing cell membrane-lipid raft microdomain from non-lipid-raft microdomain by using two fluorescence colors and simultaneously imaging microdomains and application of probe
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The invention discloses a single fluorescent probe for clearly distinguishing a cell membrane-lipid raft microdomain from a non-lipid-raft microdomain by using two fluorescence colors in a real-time in-situ manner and simultaneously imaging the microdomains. The fluorescent probe is a compound with a structure shown as a formula (I), wherein R1 expresses 2-ethoxyethyl, aminoalkyl, hydroxyalkyl or alkyl; R2 and R3 express alkyl. The invention also discloses application of the fluorescent probe in marking the lipid raft microdomain and the non-lipid-raft microdomain on a cell membrane of a living cell by using red and green fluorescence colors in the real-time in-situ manner. The probe can mark the lipid raft microdomain by using red fluorescence, and marks the non-lipid-raft microdomain by using green fluorescence at the same time, thereby realizing simultaneous imaging of the two microdomains. Compared with a current commonly-used similar probe laurdan, the probe disclosed by the invention has the characteristics that spectrum difference of two microdomains is greater, so that clear distinguishing and simultaneous imaging of the two microdomains are realized; besides, the internal problems is improved, so the probe is simpler and more convenient to operate during application and is broad in commercial application prospect.
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Paragraph 0028; 0029; 0030
(2017/08/29)
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- A carbazole as nuclear having a butterfly-shaped double-polarity micromolecule the main body material and its preparation method
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The invention discloses a butterfly-shaped bipolar small molecular host material taking carbazole as a core. The structure of the butterfly-shaped bipolar small molecular host material is as follows: electron-donating groups and electron-withdrawing groups are respectively connected to the 2nd, 3rd, 6th and 7th sites of carbazole. The bipolar small molecular host material disclosed by the invention has good electron and hole transporting capability, and can balance carrier transmission, so that more carriers can be effectively compounded in a light-emitting layer and the current efficiency of a device is improved further; meanwhile the butterfly-shaped bipolar small molecular host material also has good solubility, film-forming property and thin film morphological stability. The invention also discloses a preparation method of the bipolar small molecular host material and the preparation method has the advantages of few synthetic steps, easy feasible synthesis and easy purification, thus the preparation method can be put into industrial application favorably.
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Paragraph 0054-0056
(2017/02/28)
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- Condensed compound and organic light emitting diode comprising the same
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Provided are a condensed cyclic compound represented by chemical formula 1 and an organic electroluminescent device comprising the same. In the chemical formula 1, X, and R1 to R10 refer to the detailed description of the present invention. An organic light emitting device having an organic layer comprising the condensed cyclic compound has properties of low driving voltage, high light emitting efficiency and long lifespan.COPYRIGHT KIPO 2016
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Paragraph 0312; 0313; 0315
(2016/12/01)
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- organic semiconductor compound, manufacturing method thereof, and organic electronic device that contains it
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The present invention relates to an organic semiconductor compound, a method for manufacturing the same, and an organic electronic device comprising the same and, more specifically, to an organic semiconductor compound including quinoxaline, a method for manufacturing the same, and an organic electronic device comprising the same. In addition, by having a low band gap by synthesizing and copolymerizing a thiophene derivative containing sulfur (S) with a quinoxaline-based compound, the organic electronic device comprising the same has a higher efficiency with an innovative combination with a fullerene derivative, which is a photoactive layer, with the organic semiconductor compound of the present invention. The organic semiconductor compound of the present invention has high thermal stability and high solubility and the organic electronic device comprising the same has excellent electric characteristics, thereby can be valuably used as a n-type material of the organic electronic device, especially an organic solar cell or an organic thin film transistor.
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Paragraph 0164; 0168-0169
(2016/10/09)
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- POLYCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING THE SAME
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The present disclosure provides compounds, or pharmaceutically acceptable salts thereof, for inhibiting the growth of a microbe; treating a mammal having a microbial infection, malaria, mucositis, an ophthalmic infection, an otic infection, a cancer, or a Mycobacterium infection; killing or inhibiting the growth of a Plasmodium species; inhibiting the growth of a Mycobacterium species; modulating an immune response in a mammal; or antagonizing unfractionated heparin, low molecular weight heparin, or a heparin/low molecular weight heparin derivative.
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Page/Page column 185
(2014/07/07)
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- Supramolecular interactions of high molecular weight poly(2,7-carbazole)s with single-walled carbon nanotubes
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A novel 2,7-carbazole monomer unit was synthesized and used to prepare two poly(2,7-carbazole)s, both of which were obtained in relatively high molecular weight and display excellent solubility in common organic solvents. The polymers were able to effectively disperse carbon nanotube bundles in both THF and toluene using a relatively simple procedure to yield concentrated polymer-carbon nanotube samples that were stable for months. The polymer-coated carbon nanotube samples were characterized by thermogravimetric analysis, atomic force microscopy, absorption spectroscopy, photoluminescence mapping, and Raman spectroscopy. It was found that the polymers used in this study preferentially interact with carbon nanotubes having diameters of 1.15 nm or less. Additionally, it was observed that the carbon nanotubes remained effectively debundled by the polymers after removal of solvent, as was demonstrated by Raman and photoluminescence mapping of solid films of the polymer-carbon nanotube composites.
- Rice, Nicole A.,Adronov, Alex
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p. 3850 - 3860
(2013/07/27)
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- Synthesis and optoelectronic properties of amino-functionalized carbazole-based conjugated polymers
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A series of alcohol soluble amino-functionalized carbazole-based copolymers were synthesized via Suzuki coupling reaction. The pendent amino groups endow them high solubility in polar solvents, as well as efficient electron injection capability from high work-function metals. The relationships between the photophysical and electrochemical properties and the polymer backbone structure were systematically investigated. These alcohol-soluble carbazole-based copolymers were used as cathode interlayers between the high work-function metal Al cathode and P-PPV emissive layer in polymer light-emitting diodes with device structure of ITO/PEDOT:PSS/P-PPV/interlayer/Al. The resulting devices exhibited improved performance due to the better electron injection/transporting ability of the designed copolymers from Al cathode to the light-emitting layer.
- Liu, Shengjian,Zhang, Zhipeng,Chen, Dongcheng,Duan, Chunhui,Lu, Junming,Zhang, Jie,Huang, Fei,Su, Shijian,Chen, Junwu,Cao, Yong
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p. 1119 - 1128
(2013/09/02)
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- Efficient synthesis of N-alkyl-2,7-dihalocarbazoles by simultaneous carbazole ring closure and N-alkylation
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The N-alkyl-2,7-dihalocarbazole as the main product was formed by the reaction of 4,4′-dihalo-2-nitrobiphenyl with aromatic nitro compound and trialkyl phosphite. The presence and crucial role of aromatic nitro compound causes simultaneous carbazole ring closure and N-alkylation unlike the Cadogan ring closure where non-alkylated carbazole is formed as a main product. In addition, the mixture of aromatic nitro compound and trialkyl phosphite was found to be a possible N-alkylating agent for heterocycles, such as carbazole or indole.
- Vyprachticky, Drahomír,Kmínek, Ivan,Pokorná, Veronika,Cimrová, Věra
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experimental part
p. 5075 - 5080
(2012/07/28)
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- High-triplet-energy tri-carbazole derivatives as host materials for efficient solution-processed blue phosphorescent devices
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A novel series of solution-processible carbazole-based host materials, 3,6-bis(N-carbazolyl)-N-phenylcarbazole (BCC-36), 3,6-bis(3,6-di-tert-butyl-9- carbazolyl)-N-phenylcarbazole (BTCC-36), 2,7-bis(N-carbazolyl)-N-phenylcarbazole (BCC-27), and 2,7-bis(3,6-di-tert-butyl-9-carbazolyl)-N-phenylcarbazole (BTCC-27), is designed and synthesized. Owing to the highly twisted configuration, these hosts exhibit high triplet energy levels (2.90-3.02 eV) and high glass transition temperatures (147-210°C). They also exhibit appropriate HOMO energy levels (-5.21 - 5.36 eV), resulting in an improved hole-injection property. These novel compounds are employed to fabricate phosphorescent organic lighting-emitting diodes (OLEDs) as the host materials doped with the guests of iridium(iii) bis(4,6-difluorophenylpyridinato)- picolinate (FIrpic) and iridium(iii) bis(4′,6′- difluorophenylpyridinato)tetrakis(1-pyrazolyl)borate (FIr6) by spin coating. The best device performance of FIrpic based blue-emitting devices has a rather low turn-on voltage of 3.9 V, a maximum efficiency of 27.2 cd A-1 (11.8 lm W-1), and a maximum external quantum efficiency of 14.0%. Moreover, the best device performance of FIr6 based deep-blue-emitting devices exhibits a turn-on voltage of 4.9 V, a maximum efficiency of 11.5 cd A -1 (4.9 lm W-1), and a maximum external quantum efficiency 6.8%. The performance data are outstanding for solution-processed blue phosphorescent OLEDs. The Royal Society of Chemistry 2011.
- Jiang, Wei,Duan, Lian,Qiao, Juan,Dong, Guifang,Zhang, Deqiang,Wang, Liduo,Qiu, Yong
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experimental part
p. 4918 - 4926
(2011/10/12)
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- A 2,7-carbazole-based dicationic salt for fluorescence detection of nucleic acids and two-photon fluorescence imaging of RNA in nucleoli and cytoplasm
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A new carbazole-derived dicationic compound, namely 2,7-bis(1-hydroxyethyl- 4-vinylpyridinium iodine)-N-ethylcarbazole (2,7-9E-BHVC), with a large two-photon action absorption cross section in nucleic acids has been obtained. Moreover, it possesses the potential of imaging RNA in nucleoli and cytoplasm in two-photon fluorescence microscopy and exhibits good counterstain compatibility with the commercial fluorescent nucleic dye DAPI.
- Liu, Xin,Sun, Yuming,Zhang, Yuanhong,Miao, Fang,Wang, Guancong,Zhao, Hongshi,Yu, Xiaoqiang,Liu, Hong,Wong, Wai-Yeung
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supporting information; experimental part
p. 3615 - 3618
(2011/06/26)
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- Carbazole-linked porphyrin dimers for organic light emitting diodes: Synthesis and initial photophysical studies
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Carbazole linked porphyrin dimers were synthesized in good yields via stepwise Suzuki coupling reactions using bromoporphyrins and borylated carbazoles as the precursors, the latter of which were synthesized via known procedures from biphenyl derivatives. For comparative purposes porphyrin-carbazole monomers were synthesized. Single layer organic light emitting diodes (OLEDs) were created to demonstrate the optical properties of these materials. Light emission from these carbazole substituted porphyrins showed better results compared to previously examined bromo substituted porphyrins with better electroluminescence and lower turn-on voltages. Dimers exhibited turn-on voltages of 3 V compared to 6 V for monomeric porphyrin-carbazoles.
- Ryan, Aoife,Tuffy, Brian,Horn, Sabine,Blau, Werner J.,Senge, Mathias O.
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scheme or table
p. 8248 - 8254
(2011/11/12)
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- Synthesis and applications of 2,7-carbazole-based conjugated main-chain copolymers containing electron deficient bithiazole units for organic solar cells
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A series of low-band-gap (LBG) donor-accepor conjugated main-chain copolymers (P1-P4) containing planar 2,7-carbazole as electron donors and bithiazole units (4,4′-dihexyl-2,2′-bithiazole and 4,4′-dihexyl-5,5′-di(thiophen-2-yl)-2,2′-bithiazole) as electron acceptors were synthesized and studied for the applications in bulk heterojunction (BHJ) solar cells. The effects of electron deficient bithiazole units on the thermal, optical, electrochemical, and photovoltaic (PV) properties of these LBG copolymers were investigated. Absorption spectra revealed that polymers P1-P4 exhibited broad absorption bands in UV and visible regions from 300 to 600 nm with optical band gaps in the range of 1.93-1.99 eV, which overlapped with the major region of the solar emission spectrum. Moreover, carbazole-based polymers P1-P4 showed low values of the highest occupied molecular orbital (HOMO) levels, which provided good air stability and high open circuit voltages (Voc) in the PV applications. The BHJ PV devices were fabricated using polymers P1-P4 as electron donors and (6,6)-phenyl-C 61-butyric acid methyl ester (PC61BM) or (6,6)-phenyl-C71-butyric acid methyl ester (PC71BM) as electron acceptors in different weight ratios. The PV device bearing an active layer of polymer blend P4:PC71BM (1:1.5 w/w) showed the best power conversion efficiency value of 1.01% with a short circuit current density (Jsc) of 4.83 mA/cm2, a fill factor (FF) of 35%, and Voc = 0.60 V under 100 mW/cm2 of AM 1.5 white-light illumination.
- Patra, Dhananjaya,Sahu, Duryodhan,Padhy, Harihara,Kekuda, Dhananjay,Chu, Chih-Wei,Lin, Hong-Cheu
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experimental part
p. 5479 - 5489
(2011/06/26)
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- A novel approach to diindenocarbazoles via palladium-catalyzed intramolecular arylation
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The diindenocarbazole derivatives are synthesized by the reaction of 2,7-dibromo-9-hexylcarbazole with benzoyl chloride under Friedel-Crafts conditions, followed by Wolff-Kishner-Huang reduction to produce 3,6-dibenzyl-2,7-dibromo-9-hexylcarbazole, which was cyclized to form bis(indeno)-9-hexylcarbazole by palladium-catalyzed double intramolecular arylation. The diindeno-carbazole was further converted into fully alkylated compounds.
- Rong, Lingling,Liu, Qiancai,Tang, Jie,Chi, Zhenguo
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experimental part
p. 977 - 984
(2010/10/02)
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- Synthesis and computational studies of diphenylamine donor-carbazole linker-based donor-acceptor compounds
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The design, synthesis, and electronic spectra of a novel series of organic diphenylamine donor-carbazole linker-based donor-acceptor compounds are reported. The low-lying electronic transitions in these compounds are investigated using a combination of conventional steady-state absorption spectroscopy and tools of computational photochemistry. The electronic transitions were found to depend both on the nature of the acceptor moiety and the presence/absence of a carbazole linker, not affected by the presence of the trifluoromethlyphenyl group in all the reported DA compounds.
- Panthi, Krishna,El-Khoury, Patrick Z.,Tarnovsky, Alexander N.,Kinstle, Thomas H.
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scheme or table
p. 9641 - 9649
(2011/02/22)
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- High hole mobilities in the amorphous films of 2,7-di(9-carbazolyl)-9-(2- ethylhexyl)carbazole
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2,7-Di(9-carbazolyl)-9-(2-ethylhexyl)carbazole was synthesized and investigated as new effective hole-transporting material. The synthesized compound showed high thermal stability with the initial weight loss temperature of 400°C. It forms glass with glass-transition temperature of 88°C. Hole drift mobilities in the amorphous films of the newly synthesized compound exceeded 10-2cm2V-1 s-1 at high electric field, as characterized by the xerographic time of flight technique. Copyright
- Tomkeviciene, Ausra,Grazulevicius, Juozas V.,Jankauskas, Vygintas
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p. 344 - 345
(2008/09/20)
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- Alternating copolymers of N-(2-ethylhexyl)-carbazole derivatives with aniline units: Synthesis and properties
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Alternating copolymers such as P(3,6-EHCZ-alt-Al), P(Bis-EHCZ-alt-Al) and P(2,7-EHCZ-alt-Al), based on blue-emitting carbazole and hole-transporting triarylamine units in the polymer backbone, were successfully synthesized by using palladium-catalyzed polycondensation reaction. P(Bis-EHCZ-alt-Al) exhibited blue shift both in UV-Vis absorption and PL emission, while P(2,7-EHCZ-alt-Al) showed red shift in UV-Vis absorption and blue shift in PL emission, compared to P(3,6-EHCZ-alt-Al). It was observed from the optical and electrochemical characterization that band gap energy (2.91～3.07 eV) and HOMO (-5.25～5.11 eV) levels of the copolymers could be fine-tuned by the carbazole content in the repeating unit and different reaction linkage on the carbazole ring.
- Wang, Hui,Ryu, Jeong-Tak,Han, Yoon Soo,Kim, Dae-Hwan,Choi, Byeong Dae,Park, Lee Soon,Kwon, Younghwan
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p. 85/[365]-94/[374]
(2007/10/03)
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- Triphenylphosphine-mediated reductive cyclization of 2-nitrobiphenyls: A practical and convenient synthesis of carbazoles
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The synthesis of a series of substituted carbazoles from the corresponding 2-nitrobiphenyl derivatives using a novel modification of the Cadogan reaction is described. Cyclization of the 2-nitrobiphenyls was achieved via reductive deoxygenation of the nitro groups using a slight excess of triphenylphosphine in a suitable solvent. We have observed a temperature dependence on the extent of conversion under these conditions, with higher boiling solvents affording higher yields across a range of substrates. The new reaction conditions are very straightforward and convenient to execute, tolerate a broad range of functional groups, and yield carbazole products in the absence of unwanted side products.
- Freeman, Adam W.,Urvoy, Marie,Criswell, Megan E.
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p. 5014 - 5019
(2007/10/03)
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- Materials for injecting or transporting holes and organic electroluminescence devices using the same
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The present invention relates to a novel compound that can significantly improve the lifespan, efficiency and thermal stability of an organic light emitting device, and to an organic electroluminescence device or light emitting device comprising the compound in an organic compound layer is also disclosed.
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- En route to surface-bound electric field-driven molecular motors
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Four caltrop-shaped molecules that might be useful as surface-bound electric field-driven molecular motors have been synthesized. The caltrops are comprised of a pair of electron donor-acceptor arms and a tripod base. The molecular arms are based on a carbazole or oligo(phenylene ethynylene) core with a strong net dipole. The tripod base uses a silicon atom as its core. The legs of the tripod bear sulfur-tipped bonding units, as acetyl-protected benzylic thiols, for bonding to a gold surface. The geometry of the tripod base allows the caltrop to project upward from a metallic surface after self-assembly. Ellipsometric studies show that self-assembled monolayers of the caltrops are formed on Au surfaces with molecular thicknesses consistent with the desired upright-shaft arrangement. As a result, the zwitterionic molecular arms might be controllable when electric fields are applied around the caltrops, thereby constituting field-driven motors.
- Jian, Huahua,Tour, James M.
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p. 5091 - 5103
(2007/10/03)
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- Anti-Pneumocystis carinii pneumonia activity of dicationic carbazoles
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A series of 2,7- and 3,6-bis cationic carbazoles was synthesized and evaluated for activity against a rat model of Pneumocystis carinii pneumonia (PCP). The compounds were also tested for inhibition of topoisomerase II and binding to DNA. Several of the compounds proved to be more potent and less toxic than a standard anti-PCP drug (pentamidine). While no quantitative correlation was seen between anti-PCP activity, topoisomerase inhibition and DNA binding, a minimal level of DNA binding was found to be necessary for antimicrobial activity.
- Patrick,Boykin,Wilson,Tanious,Spychala,Bender,Hall,Dykstra,Ohemeng,Tidwell
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p. 781 - 793
(2007/10/03)
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