- Phthalimide organic light-emitting material with aggregation-induced emission and linear force stimulation-light-emitting color change response and application thereof
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The invention belongs to the technical field of organic light-emitting materials, and particularly discloses a class of phthalimide organic light-emitting materials with aggregation-induced emission and linear force stimulation-light-emitting color change
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Paragraph 0035-0037; 0040-0041
(2021/07/01)
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- Method for synthesizing carbazole derivative
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The invention aims to provide a method for synthesizing a carbazole derivative. The method is characterized in that palladium chloride is used as a catalyst, 2, 2' - dibromobiphenyl is used as an electrophilic reagent, primary amine is taken as a nucleophile, and the carbazole derivative is directly cross-coupled under the conditions of toluene as a solvent and an air atmosphere. The method has the advantages of high yield, high selectivity, simplicity and convenience in operation and the like.
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Paragraph 0013; 0048-0049
(2021/10/05)
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- Carbazole-perylenebisimide electron donor/acceptor dyads showing efficient spin orbit charge transfer intersystem crossing (SOCT-ISC) and photo-driven intermolecular electron transfer
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Perylenebisimide-carbazole (PBI-Cz) dyads were prepared to study charge-recombination (CR) induced intersystem crossing (ISC) in electron donor/acceptor dyads. The distance and the mutual orientation of the perylenebisimide (PBI) and carbazole (Cz) moieties were varied to study their effect on photophysical properties. Steady state and time-resolved optical spectroscopies show that electronic coupling between the electron donor and acceptor is negligible at the ground state. The fluorescence of the PBI moiety is strongly quenched in the dyads, and a larger separation between the donor and the acceptor results in less fluorescence quenching. The Gibbs free energy changes of the electron transfer and the energy level of the charge transfer state were studied using the electrochemical and optical spectra data. The singlet oxygen quantum yields (ΦΔ) are up to 72% for dyads with the shortest separation between the donor and the acceptor. Nanosecond transient absorption spectra confirmed the formation of the PBI-localized long lived triplet state (the lifetime is up to 190 μs). Notably non-orthogonal dyads show efficient spin orbit charge transfer (SOCT-ISC), which is different from the previously proposed orthogonal molecular structure for SOCT-ISC. Time-resolved electron paramagnetic resonance (TREPR) spectroscopy shows that all three dyads give the same electron spin polarization of eae/aea, and thus the radical pair ISC (RP ISC) mechanism is excluded, which is different from the previously reported PBI-phenothiazine analogues. Efficient and reversible transformation of dyads to their radical anion was observed in the presence of sacrificial electron donor triethanolamine in an inert atmosphere with photo-irradiation.
- Barbon, Antonio,Mahmood, Zafar,Rehmat, Noreen,Toffoletti, Antonio,Zhang, Xue,Zhao, Jianzhang
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supporting information
p. 4701 - 4712
(2020/04/22)
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- Hole transport material based on anilino carbazole and application thereof
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The invention discloses a hole transport material based on anilino carbazole. The hole transport material is a compound with a structure shown as a structural general formula (I). The compound can beused as the hole transport material, applied to a perovs
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Paragraph 0041; 0044-0045
(2020/08/18)
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- Preparation of various morphological films at nanoscale by phase separation method
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A film consisting of nanopore and nanopillar structures was produced from a binary immiscible polymer solution of poly(amic acid) (PAA) and polyimide (PI), which can be used as a potential light extraction layer or flexible substrate in organic light-emit
- Gal, Yeong-Soon,Kim, Yong Hyun,Lim, Kwon Taek,Phan, Quoc Thang,Tu, Thi Kieu Trang
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p. 127 - 134
(2020/10/02)
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- Fluorescent carbazole-containing dyes: Synthesis and supramolecular assembly by self-complementary donor-acceptor π-stacking and dipolar interactions
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Six carbazole-based dyes were synthesized by fluorescence turn on amino-ene click reactions. Two high quality single-crystals of new dyes were prepared, and their X-ray diffraction structure analyses reveal the formation of antiparallel stacking superstructures driven by self-complementary dipole-dipole and π-stacking interactions between carbazole donors and acceptors. The optical behaviors and donor-acceptor interactions of these dyes were investigated by ultraviolet–visible absorption, fluorescence emission spectroscopy, and electrochemical cyclic voltammetry. Blue fluorescence appears and increases as dye-based supramolecular polymer grows, as revealed by dynamic light scattering, fluorescence, 1H NMR and 2D NMR spectroscopy.
- Li, Fen,Li, Xiaohui,Wang, Ying,Zhang, Xin
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-
- Novel triphenylamine polyamides bearing carbazole and aniline substituents for multi-colored electrochromic applications
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A novel carbazolyl-derived diamine containing triphenylamine, 4,4′-bis[(4-aminophenyl)amino]-4″-carbazolyltriphenylamine (VI), was prepared via the reduction of 4,4′-bis[(4-nitrophenyl)amino]-4″-carbazolyltriphenylamine. A series of novel polyamides (PAs,
- Liu, Yu,Liu, Tingjun,Pang, Lifei,Guo, Jinyu,Wang, Jiuyang,Qi, Duo,Li, Wenze,Shen, Kunzhi
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- Protonation-induced dual fluorescence of a blue fluorescent material with twisted A-π-D-π-A configuration
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In this work, we introduced a blue fluorescent material with twisted A-π-D-π-A configuration, namely CzPA-F-PD. This compound exhibits remarkable dual fluorescence properties triggered by trifluoroacetic acid (TFA), resulting in blue and red emission peak
- Guo, Zhen,Liu, Xing,Liu, Zemei,Sun, Jing,Wang, Hua,Wang, Long,Xie, Guohua,Xu, Huixia,Yang, Jingjing,Zhao, Bo
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p. 2442 - 2450
(2020/03/04)
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- Triphenylamine/carbazole-modified ruthenium(ii) Schiff base compounds: Synthesis, biological activity and organelle targeting
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Four triphenylamine/carbazole-modified half-sandwich ruthenium(ii) compounds [(η6-p-cymene)Ru(N/O^N)Cl]0/+ with Schiff base chelating ligands (N/O^N) are synthesized and characterized. The introduction of Schiff base units effectively increases the antitumor activity of these compounds (IC50: 1.70 ± 0.56-17.75 ± 3.10 μM), which, meanwhile, can inhibit the metastasis of tumor cells effectively. These compounds follow an energy-dependent cellular uptake mechanism, mainly accumulate in lysosomes to destroy their integrity, and then eventually promote apoptosis. In addition, these compounds can induce an increase of intracellular reactive oxygen species (ROS) levels and provide an antitumor mechanism of oxidation, which is confirmed by the decrease of mitochondrial membrane potential (MMP) and the catalytic oxidation of the coenzyme nicotinamide-adenine dinucleotide (NADH). All these indicate that these ruthenium(ii) compounds are expected to be dual-functional antitumor agents: anti-metastasis and lysosomal damage.
- Chen, Shujiao,Ge, Xingxing,Huang, Jie,Liu, Tong,Liu, Xicheng,Liu, Zhe,Shao, Yue,Tian, Laijin,Wang, Qinghui,Yao, Meimei,Yuan, Xiang-Ai
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supporting information
p. 8774 - 8784
(2020/07/10)
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- Purpurine derivative electrochromic material and preparation method thereof
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The invention discloses a purpurine derivative electrochromic material and a preparation method thereof. The preparation method comprises the steps that 4,4'-dipyridine is adopted as a raw material and undergoes a Menschutkin reaction with 1-chloro-2,4-di
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-
Paragraph 0008; 0104; 0110-0112; 0128; 0134-0136
(2019/10/01)
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- Organic dyes containing nonsubstituted aryl amino moieties and azobenzene units for dye-sensitized solar cells
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A series of novel sensitizers were successfully synthesized utilizing azobenzene as a π-linkage unit for the D–π–A structure. A slight red shift on the absorption spectra and λonset of the sensitizers could be observed when the thienyl group was introduced to the acceptor moiety (A). In addition, replacing the donor moiety (D) from carbazole to diarylamino could lead to a negative shift (approximately 0.3 V) in the first oxidation potential. DFT calculation was also carried out and the trend of calculated HOMO–LUMO gaps was consistent to the experimental data obtained from the CV results (DT1 DT2 DT3 DT4). These sensitizers were then employed in dye-sensitized solar cells to investigate their photovoltaic performances. Highest power conversion efficiency (PCE) of 0.84% was achieved for DT1-based DSSC according to its most bathochromic absorption spectrum.
- Toan, Nguyen Duc,Chiu, Kuo Yuan,Tran, Thai Thi Ha,Yang, Te-Fang,Su, Yuhlong Oliver
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p. 1172 - 1177
(2019/08/01)
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- Base-promoted SNAR reactions of fluoro- And chloroarenes as a route to N-aryl indoles and carbazoles
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KOH/DMSO-promoted C-N bond formation via nucleophilic aromatic substitution (SNAr) between chloroarenes or fluoroarenes with indoles and carbazole under transition metal-free conditions affording the corresponding N-arylated indoles and carbazoles has been developed.
- Iqbal, Muhammad Asif,Mehmood, Hina,Lv, Jiaying,Hua, Ruimao
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- Dynamic Diels-Alder reactions of maleimide-furan amphiphiles and their fluorescence ON/OFF behaviours
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The occurrence of dynamic covalent reactions only requires relatively low activation energy, which allows both the forward and reverse reactions to proceed under mild conditions. Here, we report the design and synthesis of amphiphilic maleimide-furan adducts, where hydrophobic maleimide-based and hydrophilic furan-based moieties were connected by reversible dynamic covalent bonds. The Diels-Alder addition reactions of maleimide-furan adducts are simple, efficient, clean, and reversible without catalysts and side reactions, and occur under mild conditions. Single crystal X-ray diffraction revealed that the length of the dynamic covalent bonds is 1.56 ?, which is longer and weaker than for normal covalent bonds. The cleavage and reformation process of the dynamic covalent bonds was monitored by 1H NMR and fluorescence spectroscopy. 1H NMR spectroscopy revealed that the furan moieties of these new maleimide-furan amphiphiles can be exchanged in mixing systems due to dynamic Diels-Alder reactions; thus, two new maleimide-furan compounds can be transformed into each other. The maleimide-furan amphiphiles displayed reversible fluorescence ON/OFF behaviours and interesting H-bonding driven supramolecular assembly.
- Li, Fen,Li, Xiaohui,Zhang, Xin
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p. 7871 - 7877
(2018/11/21)
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- Triphenylamine based reactive coloro/fluorimetric chemosensors: Structural isomerism and solvent dependent sensitivity and selectivity
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Triphenyl amine based chemosensors, (2-(((2-(9H-carbazol-9-yl)phenyl)imino)methyl)-5-(diphenylamino)phenol (ortho-CPDP) and 2-(((4-(9H–carbazol-9-yl)phenyl)imino)methyl)-5-(diphenylamino)phenol (para-CPDP), showed solvent and isomerism dependent selective
- Kundu, Anu,Anthony, Savarimuthu Philip
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p. 342 - 348
(2017/08/22)
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- Carbazole stable isotope sulfhydryl compound labeling reagent as well as synthesis method and application thereof
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The invention belongs to the technical field of organic small molecule stable isotope labeling, and provides a carbazole stable isotope sulfhydryl compound labeling reagent as well as a synthesis method and application thereof. The stable isotope labeling
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- Efficient and straightforward click synthesis of structurally related dendritic triazoles
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A simple, rapid and efficient copper-catalyzed 1,3-dipolar cycloaddition reaction is described for the synthesis of a novel family of twelve triazolic dendrimers structurally related. The products were the result of the click reaction of three cores and four different azides in tetrahydrofuran applying a homogeneous copper catalysis. The reaction intermediates and products were obtained in very good to excellent yields using straightforward and simple work-up procedures. This new family of compounds contain electroactive moieties such as carbazole and triphenylamine which may turn them into excellent candidates for the development of optoelectronic organic materials.
- Mangione,Spanevello,Anzardi
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p. 47681 - 47688
(2017/10/23)
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- Copper-coordination polymer-controlled Cu@N-rGO and CuO@C nanoparticle formation: Reusable green catalyst for A3-coupling and nitroarene-reduction reactions
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The intriguing structural properties of coordination polymers (COPs), together with the huge variety of metal ions and organic linkers to choose from, make COPs potential precursors for fabricating carbon-encapsulated metal and metal oxide nanoparticles (NPs). Herein, we have studied the role of the COP structural assembly, prepared through making subtle changes to the ligand structure, on the formation of NPs in a carbon matrix. Cu-COPs (Cu-COP-1-Cu-COP-7), generated using different amino acid-based reduced Schiff base phenolic chelating ligands, exhibited crystalline structures with differing structural organization in the solid state. Interestingly, the calcination of Cu-COP-1 and Cu-COP-5 at 330 °C produced pure CuNPs, whereas Cu-COP-2, Cu-COP-3, Cu-COP-4 and Cu-COP-7 gave CuONPs encapsulated by carbon matrix. The calcination of Cu-COP-6 produced both CuNPs and CuONPs together in the carbon matrix. The formation of CuNPs and CuONPs in the carbon matrices was unambiguously confirmed by PXRD and XPS studies. The sizes and morphologies of the Cu/CuONPs were analyzed using HR-TEM and FE-SEM. BET studies revealed higher surface areas with small pores for the CuNPs encapsulated by carbon and lower surface areas with higher porosity for the CuONP-carbon matrix. Raman spectra revealed the formation of a nitrogen-doped reduced graphene oxide (N-rGO) carbon matrix in CuNPs-1. The N-rGO coverage and high surface area with small pores provided CuNPs-1 with good stability in strong acid (10 M H2SO4). Importantly, the fabricated N-rGO-encapsulated CuNPs-1 and carbon-covered CuONPs-4 nanocomposites were used as green catalysts in solvent-free neat A3-coupling and nitroarene-reduction reactions, respectively. The products were confirmed using 1H-NMR spectra. The recovered CuNPs-1 and CuONPs-4 catalysts, after the completion of the reactions, also showed similar catalytic activity at up to five cycles, without significant loss of catalytic activity. Thus, the present studies demonstrate the influence of Cu-COP structural assembly on the formation of Cu/CuONPs as well as the carbon matrix, and open the possibility of fabricating functional nanomaterials from the vast number of available COPs with intriguing structural motifs.
- Vinod Kumar, Vadivel,Rajmohan, Rajamani,Vairaprakash, Pothiappan,Mariappan, Mariappan,Anthony, Savarimuthu Philip
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p. 11704 - 11714
(2017/09/18)
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- Carbazole-based aggregation-induced emission (AIE)-active gold(I) complex: Persistent room-temperature phosphorescence, reversible mechanochromism and vapochromism characteristics
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A carbazole-based gold(I) complex 1 has been successfully synthesized. Its structure was characterized by nuclear magnetic resonance spectroscopy, elemental analysis and single crystal X-ray diffractometry. Its aggregation-induced emission behavior was studied by ultraviolet/visible, photoluminescence spectroscopy and scanning electron microscope. Its solid-state mechanochromic and thin-film vapochromic luminescence behaviors were also investigated by photoluminescence spectroscopy. The results demonstrated that luminogen 1 showed obvious aggregation-induced emission property. Furthermore, 1 also exhibited reversible high-contrast mechanochromic and vapochromic luminescence behaviors. More interestingly, 1 can emit persistent room-temperature phosphorescence with a solid-state emission lifetime up to 86.84?ms, which is the highest lifetime value among all the reported gold(I) complexes so far. To the best of our knowledge, the gold(I) complex is the first example of an AIE-active luminogen with persistent room-temperature phosphorescence, reversible mechanochromism and vapochromism characteristics.
- Chen, Zhao,Liu, Gang,Pu, Shouzhi,Liu, Sheng Hua
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p. 409 - 415
(2017/05/10)
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- Organic compound for electronic element, including the organic light emitting device and display device including the organic light emitting element
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Provided are a compound for an organic optoelectric device, an organic light emitting diode comprising same, and a display apparatus comprising the organic light emitting diode, wherein the compound for the organic optoelectric device is represented by chemical formula 1.
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- Novel functional triamine monomer containing carbazole structure and preparation method and application thereof
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The invention discloses a novel functional triamine monomer containing a carbazole structure and a preparation method and application thereof. Starting from carbazole, the novel functional triamine monomer containing carbazole is prepared through a nitration reaction, a Ullmann coupling reaction, a reduction reaction and other reactions; or starting from mono-halogenated carbazole or dihalogenated carbazole, the novel functional triamine monomer containing carbazole is prepared through a Ullmann coupling reaction, a Suzuki reaction, a reduction reaction and other reactions. The novel functional triamine monomer containing carbazole is simple in synthesis method and technology, high in yield and easy to purify, and therefore the novel functional triamine monomer containing carbazole is suitable for industrial production. The novel functional triamine monomer can be used for synthesizing hyperbranched and functional polyamide, polyimide, polyamide imide, polyester imide and other polymers.
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Paragraph 0046; 0047; 0048
(2016/10/09)
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- Synthesis of nitrocarbazole compounds and their electrocatalytic oxidation of alcohol
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Three compounds with nitrocarbazole frameworks were synthesized and their electrochemical reversibility as organic electrocatalysts was studied by cyclic voltammetry. The electrochemical reversibility and oxidation-reduction potential of the compounds were greatly affected by their substituents. The oxidation-reduction potential of the compound with an electron-donating group was negative, while that of the compound with an electron-withdrawing group on the carbazole framework was positive. The electrocatalytic oxidation activities of the nitrocarbazole compounds were investigated through cyclic voltammetry and controlled potential electrolysis at room temperature. The electrocatalysts showed excellent selectivity for p-methoxybenzyl alcohol, converting it to the corresponding aldehyde through electro-oxidation with just 2.5 mol% of the electrocatalysts presented. The electrocatalysts maintained their excellent electroredox activity following recycling.
- Zhu, Yinghong,Zhang, Jianqing,Chen, Ziying,Zhang, Anlun,Ma, Chunan
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p. 533 - 538
(2016/04/20)
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- Facile fabrication of redox-active and electrochromic poly(amide-amine) films through electrochemical oxidative coupling of arylamino groups
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Two novel electropolymerizable monomers, namely 3,5-bis(4-diphenylaminobenzamido)-N-[4-(carbazol-9-yl)phenyl]benzamide (5) and 3,5-bis(4-diphenylaminobenzamido)-N-[4-(3,6-dimethoxycarbazol-9-yl)phenyl]benzamide (5-MeO), were synthesized, and their electro
- Hsiao, Sheng-Huei,Wang, Hui-Min
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p. 2476 - 2485
(2016/07/14)
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- Preparation and electrochromic properties of two series of polyurethanes containing separated triphenylamine moiety with different blocks
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Two series of novel aromatic polyurethanes containing triphenylamine derivatives were synthesized via polycondensation of 4-(3,6-diisocyanato-9H-carbazol-9-yl) aniline, N,N-bis(4-isocyanatophenyl) benzene-1,4-diamine with various dihydroxy monomers such as phenolphthalein, 2,2-bis (4-hydroxyphenyl) -propane, 4,4'-dihydroxybiphenyl, 4, 4'-bishydroxy benzophenone and bisphenolfluorene, respectively. The variation of the backbone structure affected the electronic properties, solubility, molecular weight and thermal stability of polyurethanes. The thermal stability of polyurethanes was studied by the gravimetric analyzer. The electrochromic performance was investigated by cyclic voltammograms and spectroelectrochemical methods, which showed stable and reversible electrochromic properties. Besides, the color of polyurethanes can be varied from initial colorless to green then to blue via electro-oxidation, which indicates the polyurethanes will have potential applications for eletrochromic materials. In addition, the PUs exhibited memory characteristic. The result indicated the PUs could be applied in smart window and memory devices.
- Ji, Yan,Zhang, Chunyu,Niu, Haijun,Zhao, Xiaofeng,Wang, Cheng,Qin, Chuanli,Wang, Wen,Bai, Xuduo
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p. 106 - 115
(2015/11/16)
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- Electrochemically fabricated electrochromic films from 4-(: N -carbazolyl)triphenylamine and its dimethoxy derivative
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A carbazolyl-substituted triphenylamine derivative, 4-(N-carbazolyl)triphenylamine (TPACz), was synthesized and used to build a fluorescent and electrochromic polymeric film (PTPACz) on the ITO-glass surface by electrochemical oxidative coupling reactions
- Hsiao, Sheng-Huei,Wang, Hui-Min
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p. 43470 - 43479
(2016/05/24)
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- HOLE TRANSPORT LAYER COMPOSITION FOR SOLAR CELL, PREPARATION METHOD THEREOF AND SOLAR CELL COMPRISING THE SAME
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A hole transport layer composition is for a solar cell, a preparation method is thereof, and there is a solar cell comprising the same. More precisely, a hole transport layer composition for solar cell comprises the compound represented by formula 1. The
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-
Paragraph 0093; 0094
(2017/01/19)
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- Bipolar micromolecular luminescent material based on 4-(9H-carbazole-9-yl) aniline and preparation method and application thereof
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The invention discloses a bipolar micromolecular luminescent material based on 4-(9H-carbazole-9-yl) aniline and a preparation method and application thereof. The material is mainly characterized in that the 4-(9H-carbazole-9-yl) aniline is used as a hole transport center unit, and bipolar micromolecules with the 4-(9H-carbazole-9-yl) aniline as the center are obtained by selecting groups with an electron transmission function. The bipolar micromolecules prepared through the method can be used for making a luminescent layer of an organic light emitting diode.
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Paragraph 0039; 0040; 0041
(2016/10/09)
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- Electrosynthesis and electrochromic properties of poly(amide-triarylamine)s containing triptycene units
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Four bis(amide-triarylamine) derivatives featuring a triptycene as an interior core and terminal electroactive triphenylamine (TPA) or N-phenylcarbazole (NPC) groups were prepared by the condensation reactions from 1,4-bis(4-aminophenoxy)triptycene with 4-carboxytriphenylamine and N-(4-carboxyphenyl)carbazole, respectively, and from 1,4-bis(4-carboxyphenoxy)triptycene with 4-aminotriphenylamine and N-(4-aminophenyl)carbazole, respectively. The electrochemistry and electropolymerization of these bis(amide-triarylamine) derivatives were investigated. The stability of the oxidized forms of the bis(amide-triarylamine)s is affected by the orientation of amide linkage and the structure of terminal triarylamine unit. Two of the bis(amide-triarylamine)s could be electropolymerized into robust films on the electrode surface in an electrolyte solution. The electrogenerated polymer films exhibited reversible electrochemical oxidation processes and strong color changes upon electro-oxidation, which can be switched by potential modulation. The electrochromic properties of the films were evaluated by the spectroelectrochemical and electrochromic switching studies. The TPA-based film showed better electrochromic performance than the NPC-based one.
- Hsiao, Sheng-Huei,Chiu, Yu-Ting
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p. 90941 - 90951
(2015/11/11)
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- New triphenylamine-based poly(amine-imide)s with carbazole-substituents for electrochromic applications
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A new carbazole-derived triphenylamine-containing diimide-diacid monomer (5), 4,4′-bis(trimellitimido)-4″-N-carbazolytriphenylamine, is prepared by the condensation of 4,4′-diamino-4″-N- carbazolytriphenylamine (4) and two molar equivalents of trimellitic
- Liu, Yu,Chao, Danming,Yao, Hongyan
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p. 1422 - 1431
(2014/05/20)
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- Volatile static random access memory behavior of an aromatic polyimide bearing carbazole-tethered triphenylamine moieties
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A functional polyimide (6F/CzTPA PI), 4,4′-(hexafluoroisopropylidene) diphthalic anhydride (6FDA)/4,4′-diamino-4″-N- carbazolyltriphenylamine (DACzTPA), was synthesized in our present work for electrical resistive memory device applications. Semiconductor
- Shi, Lei,Tian, Guofeng,Ye, Hebo,Qi, Shengli,Wu, Dezhen
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p. 1150 - 1159
(2014/03/21)
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- Substituent effects on electrochemical and electrochromic properties of aromatic polyimides with 4-(carbazol-9-yl)triphenylamine moieties
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Three series of aromatic polyimides with 4-(carbazol-9-yl)triphenylamine moieties were prepared from the polycondensation reactions of 4,4′-diamino-4″-(carbazol-9-yl) triphenylamine (1), 4,4′-diamino-4″-(3,6-di-tert-butylcarbazol-9-yl)triphenylamine (t-Bu-1), and 4,4′-diamino-4″-(3,6-dimethoxycarbazol-9-yl) triphenylamine (MeO-1), respectively, with various commercially available tetracarboxylic dianhydrides. In addition to high thermal stability and good film-forming ability, the resulting polyimides exhibited an ambipolar electrochromic behavior. The polyimides based on t-Bu-1 and MeO-1 revealed higher redox-stability and enhanced electrochromic performance than the corresponding ones based on 1 because the active sites of their carbazole units are blocked with bulky t-butyl or electron-donating methoxy groups. 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 1172-1184 Three series of 4-(carbazol-9-yl)triphenylamine-based aromatic polyimides are prepared by polycondensation of corresponding diamines with various commercially available tetracarboxylic dianhydrides. All the polyimides afford flexible and tough films with high thermal stability. The polymer films show ambipolar redox and multicolored electrochromic behaviors. During the electro-oxidation processes, the polyimides with t-butyl or methoxy substituents on the pendent carbazole unit exhibit enhanced electrochemical stability and electrochemical performance, as compared with the coresponding parent polyimides, because the electrochemically active sites of carbazole are blocked. Copyright
- Wang, Hui-Min,Hsiao, Sheng-Huei
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p. 1172 - 1184
(2014/03/21)
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- Efficient synthesis of biscarbazoles by palladium-catalyzed twofold C-N coupling and C-H activation reactions
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A new and efficient strategy for the synthesis of 3,9′- and 2,9′-biscarbazoles was developed. Our strategy relies on the cyclization of 1,1′-biphenyl-2,2′-diyl bis(trifluoromethanesulfonate) with 4- or 3-anisidine, transformation of the methoxy to a triflate group and subsequent oxidative Pd-catalyzed cyclization with various anilines. This journal is the Partner Organisations 2014.
- Hung, Tran Quang,Thang, Ngo Ngoc,Hoang, Do Huy,Dang, Tuan Thanh,Villinger, Alexander,Langer, Peter
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p. 2596 - 2605
(2014/04/17)
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- Bipolar material with spiro-fluorenyl terminals: Synthesis, characterization and application for enhancement of electrophosphorescence
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We have designed a novel bipolar material (FTzCz) consisting of spiro-fluorenyl terminals and a bipolar core to enhance emission efficiency of phosphorescent light-emitting diodes based on a conventional poly(9-vinylcarbazole) host and Ir(ppy)3
- Wu, Chia-Shing,Wu, Juin-Wei,Chen, Yun
-
supporting information
p. 23877 - 23884
(2013/01/15)
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- Electrochemical and spectral characterizations of 9-phenylcarbazoles
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A series of 9-phenylcarbazoles have been synthesized and characterized for their electrochemical as well as spectral properties. For 3,6-substituted carbazoles, the oxidation is reversible and the potential is affected by the substituents. For 3,6-unprotected carbazoles, on the other hand, the oxidized forms can undergo dimerization. Their corresponding dimers have been independently synthesized by chemical methods and have exhibited identical spectral properties. The para position of the 9-phenyl group is relatively insensitive for redox and chemical reactions. The amino derivatives are unstable in carbazole cation radical form compared with their triphenylamine counterparts.
- Chiu, Ssu-Kai,Chung, Yi-Chun,Liou, Guey-Sheng,Su, Yuhlong Oliver
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scheme or table
p. 331 - 337
(2012/07/03)
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- New donor-acceptor oligoimides for high-performance nonvolatile memory devices
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We report the synthesis, optoelectronic properties, and electrical switching memory characteristics of three new donor-acceptor oligoimides consisting of the electron-donating moieties (triphenylamine or carbazole) and electron-withdrawing phthalimide moieties. The influence of different donor (D)-acceptor (A) arrangements, including D-A-D and A-D-A structures, on the electrical properties was explored. Devices based on D-A-D oligoimides revealed a reversible nonvolatile negative-differential-resistance (NDR) characteristic and excellent stability during operation. Without applying voltage stress, the on and off states of the devices showed no obvious degradation for an operation time of 10 s and 108 read pulses. However, the devices prepared from the A-D-A oligoimide showed only the insulating properties. The different memory characteristic was probably because the terminal donor moieties in the D-A-D structure might facilitate the injection and transporting of the holes. Besides, the D-A-D oligoimide with triphenylamine groups exhibited an on/off ratio of 104, 2 orders of magnitude higher than that with carbazole groups. The mechanism related to electrical switching properties was elucidated through molecular simulation. Thus the significance of D-A-D structure on tuning memory characteristics for memory device applications was revealed.
- Lee, Wen-Ya,Kurosawa, Tadanori,Lin, Shiang-Tai,Higashihara, Tomoya,Ueda, Mitsuru,Chen, Wen-Chang
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experimental part
p. 4487 - 4497
(2012/05/20)
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- Copolyfluorenes containing pendant bipolar carbazole and 1,2,4-triazole groups: Synthesis, characterization, and optoelectronic applications
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Three novel copolyfluorenes (P1-P3) containing pendant bipolar groups (2.5-7.7 mol %), directly linked hole-transporting carbazole and electron-transporting aromatic 1,2,4-triazole, were synthesized by the Suzuki coupling reaction and applied to enhance emission efficiency of polymer light-emitting diodes based on conventional MEH-PPV. The bipolar groups not only suppress undesirable green emission of polyfluorene under thermal annealing, but also promote electron- and hole-affinity of the resulting copolyfluorenes. Blending the bipolar copolyfluorenes with MEH-PPV results in significant enhancement of device performance [ITO/PEDOT:PSS/MEH-PPV+P1, P2 or P3/Ca(50 nm)/Al(100 nm)]. The maximum luminance and luminance efficiency were enhanced from 3230 cd/m2 and 0.29 cd/A of MEH-PPV-only device to 15,690 cd/m2 and 0.81 cd/A (blend device with MEH-PPV/P3 = 94/6 containing about 0.46 wt % of pendant bipolar residues), respectively. Our results demonstrate the efficacy of the bipolar copolyfluorenes in enhancing emission efficiency of MEH-PPV.
- Wu, Chia-Shing,Chen, Yun
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scheme or table
p. 3928 - 3938
(2012/07/17)
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- A novel donor-acceptor polymeric electrochromic material containing carbazole and 1,8-naphtalimide as subunit
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We report here the synthesis of a novel polymeric electrochromic material containing carbazole (Cbz)-donor and 1,8-napthalimide-acceptor as subunit. The band gap Eg was measured using UV-vis spectroscopy and compared with that obtained by cyclic voltammetry (CV). Due to intramolecular electron transfer from Cbz-donor to 1,8-napthalimide-acceptor, the fluorescence quenching was observed. When the spectro-electrochemical and electrochromic properties of polymer film were investigated, various tones of green color were obtained on the polymeric film. In the positive regime, the polymer film obtained thereby is dark green resulting from the association of carbazolylium cation radicals at oxidized state and then it can be bleached by electrochemical reduction. Besides, in the negative regime, yellowish green color of film converted to blue attributed to reduction of the 1,8-napthalimide moiety. Finally, the polymeric electrochromic exhibits multi-electrochromic behavior, high redox stability, high coloration efficiency and reasonable response time.
- Koyuncu, Fatma Baycan,Koyuncu, Sermet,Ozdemir, Eyup
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scheme or table
p. 4935 - 4941
(2010/09/06)
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- ARYLAMINE COMPOUNDS AND ELECTRONIC DEVICES
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There is provided conductive organic arylamine compounds. The compounds may be prepared as films and such films may be used as a hole transporting layer, an emissive layer or an electron transporting layer in organic light emitting devices.
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- Synthesis and electro-optical properties of carbazole containing copolymers with different conjugated structures for polymer light-emitting devices
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New copolymers such as Poly(9-(4-(2-ethyl-hexyloxy)-3,5-dimethylphenyl) carbazole-alt-aminonaphtalene) [P1] and Poly(4-(bis-methylbiphenyl-alt-9H- carbazol-9-yl)benzenamine) [P2] with chromophores separated by non-conjugated methylene spacers, and Poly(4-
- Kim, Jin Woo,Park, Eun Jung,Lyu, Eon Joo,Lee, Yun-Su,Kwon, Younghwan,Park, Lee Soon
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experimental part
p. 112/[434]-127/[449]
(2010/04/05)
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- HOLE TRANSPORT POLYMER FOR USE IN ELECTRONIC DEVICES
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Organic light emitting diode (OLED) devices are one of the most promising alternatives to liquid crystal displays (LCDs) for flat panel display (FPD) applications. The OLED technique is based on organic semiconductors used either as hole- or electron tran
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Page/Page column 12-13
(2009/06/27)
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- Synthesis and characterization of gold(I) complexes with 9-(4-isocyanophenyl)carbazole or 9-ethyl-3-isocyanocarbazole ligands
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The carbazole derivatives 9-(4-isocyanophenyl)carbazole, 3, 6-dibromo-9-(4-isocyanophenyl) carbazole, and 9-ethyl-3-isocyanocarbazole were prepared, and used to synthesize [AuX(CN-carbazole)] (X = Cl, C 6F5, C6F4/sub
- Benavente, Rut,Espinet, Pablo,Lentijo, Sergio,Martin-Alvarez, Jose M.,Miguel, Jesus A.,Rodriguez-Medina, M. Paz
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scheme or table
p. 5399 - 5406
(2010/06/13)
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- ARYLAMINE COMPOUNDS AND ELECTRONIC DEVICES
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There is provided conductive organic arylamine compounds. The compounds may be prepared as films and such films may be used as a hole transporting layer, an emissive layer or an electron transporting layer in organic light emitting devices.
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Page/Page column 23; Sheet 2/7
(2008/12/06)
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- Synthesis and optical properties of copolymers containing carbazole and 1,3,4-oxadiazole groups as blue host matrix and charge transport materials for polymer light emitting devices
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Alternating copolymers with N-arylcarbazole as hole injection and transport moieties with blue emission and 1,3,4-oxadiazole as electron transporting and hole blocking moieties were synthesized by Pd-catalyzed polycondensation reaction, and named as poly[
- Wang, Hui,Ryu, Jeong-Tak,Han, Yoon Soo,Kim, Dae-Hwan,Choi, Byeong Dae,Kwon, Younghwan
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- Green and red electrophosphorescent devices consisting of cabazole/triarylamine-based polymers doped with iridium complexes
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Two types of polymers were synthesized such as poly[N-(2-ethylhexyl) carbazole-alt-N-(4-aminophenyl)carbazole] (PECAC) and poly[N-(2-ethylhexyloxy- phenyl) carbazole-alt-N-(4-aminophenyl)carbazole] (PEPCAC). These polymers are designed to have carbazole g
- Wang, Hui,Ryu, Jeong-Tak,Kim, Dong Uk,Han, Yoon Soo,Park, Lee Soon,Cho, Ho-Young,Lee, Sam-Jong,Kwon, Younghwan
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p. 279 - 291
(2008/02/13)
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- High triplet energy polymer as host for electrophosphorescence with high efficiency
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We report the conjugated polymer P(tBu-CBP) as a host with high triplet energy (ET 2.53 eV) and suitable HOMO (5.3 eV) and LUMO (2.04 eV) energy levels. Upon doping with green and red emission Ir-complexes, it gives devices with high luminous a
- Chen, Yen-Chun,Huang, Guo-Sheng,Hsiao, Chung-Chin,Chen, Show-An
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p. 8549 - 8558
(2007/10/03)
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- Novel high-Tg poly(amine-imide)s bearing pendent N-phenylcarbazole units: Synthesis and photophysical, electrochemical and electrochromic properties
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A new carbazole-derived, triphenylamine-containing aromatic diamine monomer, 4,4′-diamino-4″-N-carbazolyltriphenylamine, was successfully synthesized by the caesium fluoride-mediated condensation of N-(4-aminophenyl)carbazole with 4-fluoronitrobenzene, followed by palladium-catalyzed hydrazine reduction. A series of novel poly(amine-imide)s 6a-6g with pendent N-phenylcarbazole units having inherent viscosities of 0.17-0.56 dL g-1 were prepared from the newly synthesized diamine monomer and seven commercially available tetracarboxylic dianhydrides via a conventional two-step procedure that included a ring-opening polyaddition to give polyamic acids, followed by chemical or thermal cyclodehydration. The polymers of the series were amorphous and most of them could afford flexible, transparent, and tough films with good mechanical properties. All the poly(amine-imide)s had useful levels of thermal stability associated with high glass-transition temperatures (303-371 °C), 10% weight-loss temperatures in excess of 543 °C, and char yields at 800 °C in nitrogen higher than 60%. The poly(amine-imide)s 6e-6g exhibited a UV-vis absorption maximum at around 300 nm in NMP solution. The poly(amine-imide) 6g derived from an aliphatic dianhydride was optically transparent in the visible region and fluoresced violet-blue at 403 nm in NMP with 4.54% quantum yield higher than the wholly aromatic 6e and 6f. The hole-transporting and electrochromic properties were examined by electrochemical and spectroelectrochemical methods. Cyclic voltammograms of the poly(amine-imide) films on an indium-tin oxide (ITO)-coated glass substrate exhibited a reversible oxidation wave at 1.05 V and an additional irreversible oxidation wave at 1.39 V versus Ag/AgCl in acetonitrile solution. The polymer films revealed excellent stability of electrochromic characteristics, with a color change from neutral pale yellowish to green doped form at applied potentials ranging from 0.00 to 1.15 V. The Royal Society of Chemistry 2006.
- Liou, Guey-Sheng,Hsiao, Sheng-Huei,Chen, Hwei-Wen
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p. 1831 - 1842
(2007/10/03)
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- Synthesis of asymmetrically arranged dendrimers with a carbazole dendron and a phenylazomethine dendron
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Asymmetrically arranged dendrimers with a carbazole dendron and a phenylazomethine dendron were synthesized by the combination of Ullmann reaction and a dehydration reaction in the presence of titanium tetrachloride. Stepwise complexation in the phenylazo
- Kimoto, Atsushi,Cho, Jun-Sang,Higuchi, Masayoshi,Yamamoto, Kimihisa
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p. 5531 - 5537
(2007/10/03)
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- Synthesis and Characterization of Monodendrons Based on 9-Phenylcarbazole
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A series of 9-phenylcarbazole ethynylene monodenrons have been prepared by palladium-catalyzed coupling reactions creating well-organized arrays of redox centers. The tert-butyl groups attached to the 3,6-positions of peripheral 9-phenylcarbazole monomers provide adequate solubility to a limited degree. Trimer and 7-mer monodendrons were prepared using a monomer with 3,3-diethyltriazene at its focal point. To facilitate purification, the synthesis of 15-mer monodendron, however, required a monomer bearing a 3-hydroxy-3-methyl-but-1-ynyl group at its focal point as a masking group for the terminal acetylene functionality. Although the solubility was limited, high generation monodendrons were found to be readily soluble in carbon disulfide, a solvent of high polarizability. Spectroscopic studies showed that there is limited through-bond conjugation over the monodendrons, but fluorescence studies suggested the presence of long-range through-space interactions in the higher members of the series.
- Zhu, Zhengguo,Moore, Jeffrey S.
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p. 116 - 123
(2007/10/03)
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- Some novel fluorescent azo compounds as intercalators for calf thymus DNA
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Two new fluorescent azo compounds, viz. 4-(diazenyl-N-phenyl-carbazolyl) phenol and 4,6-di(diazenyl-N-phenyl-carbazolyl) resorcinol have been synthesized, characterized and their noncovalent interaction studied with calf thymus DNA both in non-ionic and i
- Tripathi, Snehlata,Mohan, Mukta,Pandey, Rajendra K.,Misra, Krishna
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p. 317 - 324
(2007/10/03)
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