- Effect of Thiophene Spacer Position in Carbazole-Based Dye-Sensitized Solar Cells on Photophysical, Electrochemical and Photovoltaic Properties
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The synthesis, photophysical and electrochemical properties, and photovoltaic performances in dye-sensitized solar cells (DSSCs) of five new metal-free organic sensitizers with a carbazole moiety as the electron donor are reported. The compounds contain a thiophene at various positions and a cyanoacrylic acid unit as the electron acceptor. The position of the thiophene moiety affected both the photophysical and electrochemical properties, leading to conversion efficiencies of 1.44 to 4.57 % under AM 1.5 solar conditions (100 mW cm–2). The best performance and longest electron lifetime were found when a thiophene was located on both donor and acceptor sites. The DSSC showed a short-circuit current (Jsc) of 8.59 mA/cm2, an open-circuit photovoltage (Voc) of 0.75 V, and a fill factor (FF) of 0.71. The position of the π-conjugated bridges not only affects the absorption spectra and the energy levels of the sensitizers, but also adjusts the electron lifetime.
- Samae, Ruslan,Surawatanawong, Panida,Eiamprasert, Utt,Pramjit, Songyos,Saengdee, Laksana,Tangboriboonrat, Pramuan,Kiatisevi, Supavadee
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- Cavity-directed nitroaromatics sensing within a carbazole-based luminescent supramolecular M2L3 cage
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The design and preparation of luminescent M2L3 metal-organic cage via the coordination-driven self-assembly of carbazole-based ligand with a V-shaped geometry is described. The cage Zn-L1 with an open cavity which equipped aromatic rich ligands shows the highest emission quenching efficiency towards picric acid than other nitroaromatic explosives. The quenching ability depended on whether there formed the host-guest molecules are well explored by electrospray ionization mass spectrometry (ESI-MS), and isothermal titration microcalorimetry (ITC).
- Feng, Tianchi,Li, Xuezhao,Wu, Jinguo,He, Cheng,Duan, Chunying
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- Development in synthesis and electrochemical properties of thienyl derivatives of carbazole
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A convenient and higher yielding synthetic route to N-alkyl-bis(thiophene)- and N-alkyl-bis(ethylenedioxythiophene) carbazole derivatives is reported and their aggregation, and electrochemical properties are characterized. The key step in the synthesis of this group of compounds has been the Stille-type coupling reaction between the N-alkyldibromocarbazole and tin derivatives of thiophene or ethylenedioxythiophene, as the best way for preparation of conjugated N-alkylcarbazole derivatives. For this group of compounds we also present an electrochemical polymerization effect.
- Cabaj, Joanna,Idzik, Krzysztof,So?oducho, Jadwiga,Chyla, Antoni
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- Violet/deep-blue fluorescent organic light-emitting diode based on high-efficiency novel carbazole derivative with large torsion angle
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A novel and highly efficient violet/deep-blue fluorescent carbazole and naphthalene-based compound (1) is designed and synthesized. The compound shows intensive violet/deep-blue fluorescence, high photoluminescence efficiency (0.72 in CH2Cl2, 0.65 in film) and narrow full width at half maximum (48 nm). The large torsion angles between carbazole and naphthalene guarantee the weak intermolecular interactions and suppress the π-π interactions in solid state, resulting in the highly efficient violet/deep-blue fluorescence. The maximum emission peak, luminance and external quantum efficiency for violet/deep-blue electroluminescence are 410 nm, 1326 cd/m2 and ~2%, respectively.
- Feng, Xiaoting,Wei, Xiaozhen,Yin, Mengna,Miao, Yanqin,Tao, Peng
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- Utilizing the heterocyclic effect towards high contrast ratios of mechanoresponsive luminescence based on aromatic aldehydes
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A high contrast ratio is required by mechanoresponsive luminescent (MRL) materials to enable their adoption in mechanical sensors. However, the effective design principle remains restricted by the lack of understanding of the necessary features of such lu
- Zhang, Fang,Liang, Xiaozhong,Li, Da,Yin, Xiangkai,Tian, Xia,Li, Bin,Xu, Hong,Guo, Kunpeng,Li, Jie
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- Cyclo[4]carbazole, an Iodide Anion Macrocyclic Receptor
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A novel preorganized and rigid iodide anion macrocyclic receptor, cyclo[4]carbazole (Cy[4]C), is reported here. The structure of Cy[4]C was confirmed by single-crystal X-ray analysis. The binding affinity of Cy[4]C for iodide anion was investigated by UV-vis and 1H NMR spectroscopic techniques. The crystal structure of the complex between Cy[4]C and chloroform also provided evidence for the recognition ability of Cy[4]C toward iodide anion. Furthermore, the 1:1 complexation stoichiometry between Cy[4]C and iodide anion was confirmed by high-resolution mass spectrometry and molecular modeling.
- Zhu, Huangtianzhi,Shi, Bingbing,Chen, Kexian,Wei, Peifa,Xia, Danyu,Mondal, Julfikar Hassan,Huang, Feihe
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- A conjugated hyperbranched polymer constructed from carbazole and tetraphenylethylene moieties: Convenient synthesis through one-pot "a 2 + B4" Suzuki polymerization, aggregation-induced enhanced emission, and application as explosive chemosensors and PLEDs
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In this paper, tetraphenylethylene (TPE) units, a well-known aggregation-induced emission (AIE) active group, are utilized to construct the hyperbranched polymer HP-TPE-Cz with carbazole moieties, a good hole-transporting and electroluminescent group, through an "A2 + B4" approach by using a one-pot Suzuki polycondensation reaction. For comparison, its analog linear polymer LP-TPE-Cz, also constructed from these two moieties, was prepared. These two polymers exhibit interesting aggregation-induced emission enhanced (AIEE) behavior and act as explosive chemosensors with high sensitivity both as nanoparticles and in solid state, due to the presence of TPE units. Also, the HP-TPE-Cz PLED device exhibited a remarkably enhanced current efficiency (2.13 cd A-1) and luminescence efficiency (5914 cd m-2), compared with its analog linear polymer LP-TPE-Cz (1.04 cd A-1, 1654 cd m-2). The Royal Society of Chemistry 2012.
- Wu, Wenbo,Ye, Shanghui,Huang, Lijin,Xiao, Li,Fu, Yingjie,Huang, Qi,Yu, Gui,Liu, Yunqi,Qin, Jingui,Li, Qianqian,Li, Zhen
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- A containing carbazolyl ultraviolet absorbent and its preparation method (by machine translation)
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The invention discloses a containing carbazolyl ultraviolet absorbent and its preparation method, the ultraviolet absorbent of the chemical name is 3, 6 - di (2 - bromo - 5 - thienyl) - 9 - butyl carbazole, molecular formula is C24 H19 NBr2 S2 , It can at the same time keeping the light absorption performance of quenching fluorescence, the product is maintained colorless transparent characteristics. (by machine translation)
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Paragraph 0009; 0012
(2018/07/30)
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- Π-acceptor and donor-type compd. dye for dye-sensitized solar cell
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PROBLEM TO BE SOLVED: To provide a donor-π-acceptor type compound capable of improving an adsorption amount to a metal oxide, and a dye for a dye-sensitized solar cell.SOLUTION: A donor-π-acceptor type compound has two acceptors in one molecule, the acceptors being one selected from the group consisting of a pyridine-containing group and a pyridinium ring-containing group which have adsorption ability to a metal oxide. The donor-π-acceptor type compound includes two donor-π-acceptor structures where a donor and π are conjugated and a π conjugate structure is not branched.
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Paragraph 0043-0044
(2018/04/20)
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- Carbazole-bridged double D-A dye for efficient dye-sensitized solar cell
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A di-anchoring organic dye based on an acceptorπ spacerdonorsecondary donordonorπ spacer acceptor structural motif has been synthesized and used as a sensitizer for dye-sensitized solar cells (DSSCs). The new synthetic approach uses two π spacers, two acceptors and two different donors such as arylamino and carbazole units. The double donoracceptor dye CBZ-3 is linked by a carbazole unit as a secondary donor which increases the donoracceptor strength of the dye and proved to increase the η and Jsc values of the photovoltaic cell compared to the corresponding mono-anchoring system CBZ-2 and the monodonor dye CBZ-1. With the non-planar structure of the arylamino group and the alkyl chains which efficiently prevent the formation of the dye aggregates, the dye exhibited a high open-circuit photovoltage (Voc) of 650 mV, a short-circuit photocurrent density (Jsc) of 7.20 mA cm-2 and the solar energy-to-electricity conversion efficiency (η) of 3.23%.
- Pramjit, Songyos,Eiamprasert, Utt,Surawatanawong, Panida,Lertturongchai, Pattida,Kiatisevi, Supavadee
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- Structure-properties relationship of the derivatives of carbazole and 1,8-naphthalimide: Effects of the substitution and the linking topology
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Nine compounds having electron-accepting 1,8-naphthalimide and electron-donating carbazole moieties were synthesized employing palladium-catalyzed C-N and C-C coupling reactions and characterized by the thermal methods, absorption and emission spectrometry, electrochemical and photoelectrical tools. The synthesized compounds possess high thermal stability with the 5% weight loss temperatures being in the range of 351-476 °C. Most of the synthesized compounds are capable of glass formation with glass transition temperatures ranging from 30 to 87 °C. The cyclic voltammetry measurements showed that the solid state ionization potentials values of the carbazole and 1,8-naphthalimide derivatives range from 5.46 eV to 5.76 eV and the electron affinities values range from -3.04 eV to -2.92 eV. Dilute solutions of the 3- and 3,6-naphthalimide-substituted derivatives of carbazole in polar solvents were found to emit in the green region with quantum yields ranging from 0.66 to 0.83, while in the solid state fluorescence quantum yields were found to be in the range of 0.01-0.45. ((E)-9-(((N-(2-ethylhexyl)-1,8-naphthalimide)-4-yl)ethenyl)-9H-carbazole) exhibited efficient fluorescence in the solid state with quantum yield as high as 0.45. The effects of the linking topology of the chromophores and of the incorporated alkyl substituents on the thermal, optical, and photoelectrical properties of the synthesized donor-acceptor compounds are analyzed. The impact of the ground state intramolecular twisting of the carbazole and naphthalimide moieties induced by the substituents resulting in significant variation in the rates of radiative and nonradiative excitation deactivation is revealed.
- Gudeika, Dalius,Grazulevicius, Juozas Vidas,Volyniuk, Dmytro,Butkute, Rita,Juska, Gytis,Miasojedovas, Arunas,Gruodis, Alytis,Jursenas, Saulius
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p. 239 - 252
(2015/03/31)
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- Synthesis and blue-violet two-photon excited fluorescence of a new organoboron compound
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A new A-π-D-π-A type organoboron compound, 3,6-bis(dimesitylboryl)-N-butyl-carbazole (abbreviated as BBC), with trivalent boron as electron acceptor and carbazole as electron donor and π-conjugated core, has been synthesized and its single and two-photon
- Cao, Duxia,Liu, Zhiqiang,Li, Guozhong,Liu, Guoqun,Zhang, Guohui
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- Synthesis of a nanocar with an angled chassis. Toward circling movement
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(Chemical Equation Presented) Nanocars with an angled chassis have been synthesized and imaged using scanning tunneling microscopy. These angled chassis nanocars were designed to further our understanding of the directional control and surface-rolling capabilities of this class of nanomachines. The alkylated carbazole inner core might enable the molecular scaffold to produce circular rolling motions of the nanovehicles on surfaces.
- Sasaki, Takashi,Osgood, Andrew J.,Alemany, Lawrence B.,Kelly, Kevin F.,Tour, James M.
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p. 229 - 232
(2008/09/18)
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- PLED devices containing triphenylamine-derived polyurethanes as hole-transporting layers exhibit high current efficiencies
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The innovative polyurethane-type polymers from a triphenylamine derivative, [N,N′-bis(4-hydroxyphenyl)-N,N′-diphenylbenzidine] (TPA) and a carbazole derivative, [9-butyl-3,6-bis(4-hydroxyphenyl)carbazole] (Cz) can be linked through isophorone diisocyanate (IPDI) bridges and incorporated as hole-transporting layers in high-performance PLED devices. The TPA-IPDI-Cz type of polyurethane (PU) materials (P1-P5) showed superb hole injection and transport properties based on the results of the hole-only-device study. We prepared the devices in two kinds of configuration: system (1) Indium Tin Oxide (ITO)/PU (20 nm)/{Iridium(iii) bis(2-phenylpyridine), [Ir(ppy)3] + 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (t-PBD) + polyvinylcarbazole (PVK)] (50 nm)/Mg (10 nm)/Ag (100 nm), for the device with P1 (DP1), the brightness increased to 14000 cd m-2, the current efficiency rose to 13.4 cd A-1, and the turn-on voltage was reduced to 21 V (at 100 cd m-2). In system (2) ITO/PEDOT-PSS (30 nm)/PU (20 nm)/[Ir(ppy)3 + t-PBD + PVK] (50 nm)/Mg (10 nm)/Ag (100 nm), with PEDOT-PSS as the hole-injection layer, was compared to the standard device (S2) having the configuration ITO/PEDOT-PSS (50 nm)/[Ir(ppy)3 + t-PBD + PVK] (50 nm)/Mg (10 nm)/Ag (100 nm); the brightness of the double layer device with P5 (DDP5) increased to 12500 cd m-2 and the current efficiency dramatically rose to 34.7 cd A-1, compared with values of 6250 cd m-2 and 21.8 cd A-1, respectively, for S2. The Royal Society of Chemistry.
- Ku, Cheng-Hsiu,Kuo, Chao-Hui,Chen, Chih-Yi,Leung, Man-Kit,Hsieh, Kuo-Huang
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supporting information; experimental part
p. 1296 - 1301
(2009/06/18)
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- Synthetic routes toward carborane-wheeled nanocars
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(Chemical Equation Presented) A new set of aryleneethynylene derivatives bearing three, four, and six p-carboranes as potential wheels attached to a semirigid chassis have been designed and synthesized. These molecules are expected to move in predetermined patterns on atomically smooth surfaces, depending on their specific configuration.
- Morin, Jean-Francois,Sasaki, Takashi,Shirai, Yasuhiro,Guerrero, Jason M.,Tour, James M.
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p. 9481 - 9490
(2008/03/17)
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- Reactivity of silyl monomers for the oxidative polymerization of phenylene units
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Oxidative coupling of silyl monomers containing phenylene units was performed electrochemically and chemically using FeCl3 as oxidant. 2,5-Trimethylsilyl-1,4-dihexoxybenzene led to poly (2.5-dihexoxyparaphenylene) with a degree of polymerization higher than the one obtained upon oxdative coupling of non silyl monomers. The coupling reaction was however moderately improved in the case of 3,6-bis-dimethylsilyl(N-n-butylcarbazole). The role of the silyl substituents during the oxidative polymerization is dicussed.
- Bouachrine, Mohammed,Lere-Porte, Jean-Pierre,Moreau, Joel J. E.
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p. 265 - 278
(2007/10/03)
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