- Synthesis and luminescent properties of novel organic luminescent materials based on carbazole derivatives
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Four novel host materials C1–C4 based on carbazole derivatives have been designed, synthesized, characterized, and applied as organic light-emitting devices. This report presents a novel approach, which combines carbazole and aromatic hydrocarbons through methylene. The formed molecules exhibited twisted structures, which resulted in high glass transition temperatures (Tg), ranged from 90.4 to 148.0?°C. They also had high optical bandgaps (Eg), their optical energy bandgaps are determined by absorption edge technique as 3.22 to 3.50?eV, evaluated photo-physical properties of these synthesized novel chromophores, the optical properties such as maximum absorption and emission wavelengths (λ, nm), molar extinction coefficients (ε, cm? 1 M? 1), Stoke’s shifts (ΔλST, nm), and quantum yields (φF) also studied the effect of solvent polarity on absorption and emission of these carbazole derivatives, and these compounds exhibited intense absorption bonds between 250 and 325?nm, which are attributed to the π–π* transition of the carbazole-centered units. In addition, they showed blue fluorescence in different solvents. These compounds showed bathochromic shift with the increase in the solvent polarity.
- Duan, Yingxiang,Yang, Yanhua,Cen, Bo,Shen, Kecheng,Tao, Xian,Shen, Yingzhong
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- Syntheses, characterizations and electrochromic applications of polymers derived from carbazole containing thiophene rings in side chain with electrochemical and FeCl3 methods
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1,8-Bis(3,6-di(thiophen-3-yl)-9H-carbazol-9-yl)octane (BDTCO) was synthesized via Ullmann and Suzuki couplings. Additionally, its homopolymer and copolymers with 3,4-ethylenedioxythiophene (EDOT), pyrrole (Py) and thiophene (Th) were synthesized and coated onto an ITO-glass surface via electrochemical oxidative polymerization. The spectroelectrochemical and electrochromic properties of the polymers were also investigated. The switching ability of these polymers was measured as the percent transmittance (T%) at their point of maximum contrast. Moreover, the polymer of BDTCO (P-BDTCO) was successfully synthesized through FeCl3 oxidative polymerization. The compounds were characterized by FT-IR, NMR and X-ray Photoelectron Spectroscopy (XPS), and their thermal stabilities were determined via TG measurements. The solid state conductivities of the polymeric films coated onto the ITO-glass surface were measured via the four point probe technique using an electrometer. In addition, the surface morphological properties were investigated by Scanning Electron Microscopy (SEM) for different magnifications.
- Aydin, Aysel,Kaya, Ismet
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- Synthesis and characterization of two carbazole-based alternating copolymers with 4-nitrophenylcyanovinylene pendant groups and their use as electron donors for bulk heterojunction solar cells
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Two new carbazole-based copolymers PT and PP carrying thienyl or phenyl, respectively, alternating segments and 4-nitrophenylcyanovinylene pendant groups attached to the carbazole nitrogen were synthesized and characterized. Their optical and electrochemical properties were investigated. Both copolymers showed broad absorption bands in the longer wavelength region, which is complementary to those of PC61BM and PC71BM acceptors, and showed optical band gaps about 1.64 eV and 1.69 eV for PT and PP, respectively. The deep lying HOMO energy level benefited a high open circuit voltage (V oc), leading to an overall power conversion efficiency (PCE) of 2.19%, 2.98% 2.02% and 2.54% for bulk heterojunction (BHJ) solar cells based on PT:PC61BM, PT:PC71BM, PP:PC61BM and PP:PC 71BM blends, respectively, processed from tetrahydrofuran (THF) solvent. The BHJ solar cells based on PT:PC71BM and PP:PC 71BM blends processed from THF and 1-chloronaphthalene (CN) mixed solvents showed overall PCE of about 5.39% and 4.20%, respectively. The increase in the overall PCE for the BHJ devices based on solvent additives was attributed to the balanced charge transport in the devices. The Royal Society of Chemistry 2013.
- Sharma,Singh, Manjeet,Kurchania, Rajnish,Koukaras,Mikroyannidis
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- Synthesis and characterization of red light-emitting electrophosphorescent polymers with different triplet energy main chain
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Red light-emitting electrophosphorescent polymers with poly(fluorene-alt- carbazole) (PFCz) and poly(3,6-carbazole) (PCz) as the main chain, and the quinoline-based iridium (Ir) complex as the side chain have been synthesized by Suzuki and modified Yamamoto polymerization, respectively. The triplet energy of the polymeric backbone is tuned from 2.1 eV of polyfluorene (PF) to 2.3 eV of PFCz and 2.6 eV of PCz. We find that, with the increasing triplet energy, the lifetime of the triplet excitons gradually increases, but the device efficiency becomes worse. The reason is that the alteration of the main chain structure leads to the increase of the highest occupied molecular orbital (HOMO) level of the polymeric host, which can facilitate the efficient hole injection and transportation. As a consequence of this enhancement of the hole current, charge balance in the emitting layer is destroyed, and correspondingly, the poorer device performance is achieved. Our results, we believe, indicate that besides the triplet energy, charge balance is a crucial determinant to develop high efficiency red light-emitting electrophosphorescent polymers.
- Ma, Zhihua,Ding, Junqiao,Cheng, Yanxiang,Xie, Zhiyuan,Wang, Lixiang,Jing, Xiabin,Wang, Fosong
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- Organic dyes containing fused acenes as building blocks: Optical, electrochemical and photovoltaic properties
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Two D-π-A dyes based on fused acenes (carbazole, cyclopenta[2,1-b:3,4-b’]dithiophene (CPDT) and dithieno[3,2-b:2’,3’-d]pyrrole (DTP)) were synthesized, characterized using UV-vis absorption spectroscopy and electrochemistry, density function theory (DFT) calculations, and used as sensitizers in dye-sensitized solar cells (DSSCs). The two sensitizers were compared thoroughly over physicochemical properties and DSSC performance. Although the DTP dye has slightly blue-shifted and weaker incident photon-to-collected electron (IPCE) conversion efficiency responses, the much increased open-circuit photovoltage values and improved charge-transfer kinetics relative to the CPDT systems result in superior power conversion efficiencies. This work reveals the potential of DTP as a bridge in the design of sensitizers.
- Gao, Peng,Tsao, Hoi Nok,Teuscher, Joel,Gr?tzel, Michael
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- Blue light-emitting polyfluorenes containing dibenzothiophene-S,S-dioxide unit in alkyl side chain
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Blue light-emitting polyfluorenes containing dibenzothiophene-S,S-dioxide (SO) unit in alkyl side chain (PF-FSOs and PF-CzSOs) were synthesized. All the polymers show high thermal stability with the decomposition temperatures over 400 °C. The highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energy levels of the copolymer slightly decrease with the increase of SO content in side chain. PL spectra of the polymers show slightly red shift and broadening with the increase of solvent polarities, indicating unremarkable intramolecular charge transfer (ICT) effect in the polymers containing SO unit in alkyl side chain. EL spectra of the polymers are almost unchanged in the current densities from 100 to 400 mA cm?2, indicating the superb EL stability of the resulted polymers. The EL spectra of the copolymers exhibit obvious blue-shift and narrowing with the CIE of (0.18, 0.11) for PF-FSO10 and (0.17, 0.11) for PF-CzSO10, respectively, compared with PF-SO10 containing SO unit in main chain with the CIE of (0.16, 0.17) and PFO with the CIE of (0.18, 0.18). The superior device performances were obtained with the luminous efficiency (LEmax) of 1.17 and 0.68 cd A?1 for PF-FSO15 and PF-CzSO20, respectively, compared with the LEmax of 0.37 cd A?1 for PFO. The results indicate that linking SO unit to alkyl side chain of the polyfluorene is a promising strategy for efficient blue light-emitting polymers.
- Fang, Yiwen,Liu, Jie,Zhang, Yuhao,Guo, Ting,Huang, Fei,Yang, Wei,Cao, Yong
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- Hydrogen-Bonded Crystalline Molecular Machines with Ultrafast Rotation and Displacive Phase Transitions
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Two new crystalline rotors 1 and 2 assembled through N?H???N hydrogen bonds by using halogenated carbazole as stators and 1,4-diaza[2.2.2]bicyclooctane (DABCO) as the rotator, are described. The dynamic characterization through 1H T1 relaxometry experiments indicate very low rotational activation barriers (Ea) of 0.67 kcal mol?1 for 1 and 0.26 kcal mol?1 for 2, indicating that DABCO can reach a THz frequency at room temperature in the latter. These Ea values are supported by solid-state density functional theory computations. Interestingly, both supramolecular rotors show a phase transition between 298 and 250 K, revealed by differential scanning calorimetry and single-crystal X-ray diffraction. The subtle changes in the crystalline environment of these rotors that can alter the motion of an almost barrierless DABCO are discussed here.
- Colin-Molina, Abraham,Jellen, Marcus J.,Rodríguez-Hernández, Joelis,Cifuentes-Quintal, Miguel Eduardo,Barroso, Jorge,Toscano, Rubén A.,Merino, Gabriel,Rodríguez-Molina, Braulio
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- Synthesis and optical characterization of bipod carbazole derivatives
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In this study, some new biscarbazole derivatives were synthesized for the purpose of being used in OLED technologies and related areas. The following compounds: {1,2-bis(2-(3,6-diphenyl-9H-carbazole-9-yl) ethoxy)ethane (C-1), bis[2-(2-(3,6- diphenyl-9H-carbazole-9-yl) ethoxy)etyl]ether (C-2), bis[2-(2-(3,6-di(naphthalene-1-yl)-9H-carbazol-9-yl)ethoxy)etyl]ether (C-3) and bis [2-(2-(3,6-di(naphthalene-2-yl)-9H-carbazol-9-yl)ethoxy) ethyl]ether (C-4) were synthesized by Suzuki-Miyaura Cross Coupling reactions. The structural properties of the synthesized compounds were characterized by FT-IR, 1H-NMR, 13C-NMR, and LC-MS. The maximum product yields of 81.6% were obtained for C-4 biscarbazole derivatives. The optical properties were studied using UV-visible and temperature/excitation power density dependent photoluminescence (PL) techniques. The emissions were observed at green and yellow-red color spectral bands. By applying Gaussian fitting to the measured spectra, the superposition of the broad peaks was deconvoluted into two peaks. The origin of emissions was attributed to π- π? transition in aromatic compounds caused by intramolecular charge transfer from host carbazole to these compounds.
- ?a?ll, Merve,?i?ek, Baki,Tülek, Remziye,Teke, Ali
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- Synthesis and characterization of yellow and green light emitting novel polymers containing carbazole and electroactive moieties
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The compounds 1,5-bis(3,6-di(thiophen-3-yl)-9H-carbazol-9-yl)pentane (B1) and 1,2-bis(2-(3,6-di(thiophen-3-yl)-9H-carbazol-9-yl)ethoxy)ethane (B2) were synthesized via Ullmann and Suzuki couplings. Additionally, the homopolymers and copolymers of these compounds with 3,4-ethylenedioxythiophene (EDOT) and thiophene (Th) were synthesized and coated onto an ITO-glass surface via electrochemical oxidative polymerization. The spectroelectrochemical and electrochromic properties of these compounds were also investigated. The switching ability of these polymers was measured as the percent transmittance (%T) at their point of maximum contrast. The solid state electrical conductivities of the polymeric films coated onto the ITO-glass surface were measured via the four point probe technique using an electrometer. The compounds were characterized by FT-IR and NMR, and their thermal stabilities were determined via TG measurements. Fluorescence measurements were performed using DMSO solutions, and the synthesized polymers emitted both green and yellow colors based on the tuning of the excitation wavelength, which indicates that these polymers could be used to produce new polymeric light emitting diodes (PLEDs) with green and yellow emissions.
- Aydin, Aysel,Kaya, Ismet
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- Preparation and properties of poly[9-hexadecyl-3-phenyl-6-(4-vinylphenyl)- 9H-carbazole]
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Preparation of new carbazole-containing polymer, poly[9-hexadecyl-3-phenyl- 6-(4-vinylphenyl)-9H-carbazole], is reported. The optical properties of the product have been studied in comparison with those of the starting compounds. Electrochemical properties of the polymer solution and its thin film have been investigated. The polymer film images were obtained by atomic force and scanning tunneling microscopy. Thermogravimetric analysis has shown high thermal stability of the obtained polymer.
- Bakiev,Shklyaeva,Lunegov,Mokrushin,Abashev
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- Synthesis and characterization of 1,3,5-triphenylamine derivatives with star-shaped architecture
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In this work we report the synthesis, electrochemical and optical properties of five new, star shaped compounds containing both carbazole and triphenylamine moieties, further endcapped with thiophene or 3,4-ethylenedioxythiophene units. Electrochemical, UV-visible spectroscopy and fluorescence methods were employed to study the properties of these compounds as well as their electropolymers. The basic characteristics such as the band gaps, HOMO and LUMO values, absorption and emission maximum wavelengths of the monomers and the polymers are reported and discussed.
- Brzeczek, Alina,Karon, Krzysztof,Higginbotham, Heather,J?drysiak, Rafa? G.,Lapkowski, Mieczyslaw,Walczak, Krzysztof,Golba, Sylwia
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- A fluorescent lanthanide-organic framework for highly sensitive detection of nitroaromatic explosives
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A lanthanide-organic framework constructed from a new π-electron rich ligand 5,5′-(9H-carbazole-3,6-diyl)diisophthalic acid (H4L) and Tb(NO3)3·6H2O, namely, [(CH3)2NH2][TbL] (1), has been synthesized under solvothermal condition. X-ray diffraction analysis reveals that complex 1 exhibits a 3D porous framework featuring a (4,8)-connected sqc net. The solid sample of 1 exhibits strong green fluorescence in the visible region upon excitation at 354?nm. The fine grinding particles of 1 dispersed in ethanol shows good sensitivity for picric acid (PA), which can be reused at least five times for detecting PA. The good sensitivity and recyclability of 1 make it a potential fluorescent sensor for explosives detection.
- Mu, Yajuan,Ran, Yungen,Du, Jianlong,Wu, Xueyi,Nie, Weiwei,Zhang, Jianhong,Zhao, Ying,Liu, Huan
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- Synthesis and spectroelectrochemical characterization of multi-colored novel poly(3,6-dithienylcarbazole) derivatives containing azobenzene and coumarin chromophore units
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Azobenzene and coumarin units bearing four novel 3,6-linked thiophene-carbazole-thiophene type electroactive monomers were synthesized in order to observe the effects of strong chromophore units on the electrochemical and spectroelectrochemical behaviors of resulting π-conjugated conducting polymers (PTCbzAz, PECbzAz, PTCbzCo and PECbzCo). Electronic and optoelectronic properties of all polymers were investigated by cyclic voltammetry and in situ spectroelectrochemical studies, and their oxidation potentials, HOMO/LUMO energy levels, band gaps (Egop), optical contrasts (ΔT%) and switching times were reported in detail. It was observed that incorporation of strong chromophore units in polymer backbones resulted in poly(3,6-dithienylcarbazole) derivatives with different optical band gap values and different number of colored states. The optical band gap values for PECbzAz, PECbzCo, PTCbzAz, PTCbzCo and were calculated as 1.71 eV, 1.75 eV, 1.93 eV and 2.07 eV, respectively, from the onset of π-π?transition in polymer films' neutral state absorptions. All polymers exhibited multicolored electrochromic behavior upon extarnally applied potential. Reported electrochemical and optical features of PECbzAz, PECbzCo, PTCbzAz, PTCbzCo suggest that these poly(3,6-dithienylcarbazole) derivatives are promising candidates for multicolored electrochromic device applications.
- Yi?it, Deniz,Hacioglu, Serife O.,Güllü, Mustafa,Toppare, Levent
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- Architectural design of new conjugated systems carrying donor-π-acceptor groups (carbazole-CF3): Characterizations, optical, photophysical properties and DSSC's applications
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In this study, two new organic dyes containing substituted N-octyl carbazole as electron donor and -CF3 units as electron acceptor group were designed and synthesized for ZnO-based dye sensitized solar cells (DSSCs). The synthesized carbazole derivatized compounds 3,6-bis(3,5-bis(trifluoromethyl)phenyl)-9-octyl-9H-carbazole (IVa) and 3,6-bis(4-(trifluoromethyl)phenyl)-9-octyl-9H-carbazole (IVb) were characterized by FT-IR, 1H NMR, 13C NMR, HMBC and CHN analyses. The spectroscopic (UV–Vis and FL) and thermal properties (TGA-DTA) of these compounds were also investigated. The produced (IVa and IVb) ZnO films were used as photoanodes in all DSSCs. Microwave-assisted hydrothermal method was used to synthesize ZnO nanopowders with different morphologies which are used as photoanodes in DSSCs. The structural and morphological properties of ZnO nanopowders were investigated using X-ray diffraction (XRD) and field emission scanning electron microscopy (FESEM). ZnO-DSSCs were produced through coating ZnO nanopowders on transparent conductive fluorine-doped tin oxide (FTO) coated glass substrate using the Doctor Blade method. Current-voltage measurements of all produced DSSCs were carried out under a solar simulator with AM 1.5 G filter having an irradiance of 100 mW/cm2. Solar cell performances of all DSSCs such as; open-circuit voltage (Voc), short circuit current (Jsc), fill factor (FF) and power conversion efficiency (PCE) were analyzed.
- Caglar, Mujdat,Caglar, Yasemin,Derince, Betul,Gorgun, Kamuran
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- Functionalization of biphenylcarbazole (CBP) with siloxane-hybrid chains for solvent-free liquid materials
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We report herein the synthesis of siloxane-functionalized CBP molecules (4,4′-bis(carbazole)-1,1′-biphenyl) for liquid optoelectronic applications. The room-temperature liquid state is obtained through a convenient functionalization of the molecules with heptamethyltrisiloxane chains via hydrosilylation of alkenyl spacers. The synthesis comprises screening of metal-catalyzed methodologies to introduce alkenyl linkers into carbazoles (Stille and Suzuki Miyaura cross-couplings), incorporate the alkenylcarbazoles to dihalobiphenyls (Ullmann coupling), and finally introduce the siloxane chains. The used conditions allowed the synthesis of the target compounds, despite the high reactivity of the alkenyl moieties bound to π-conjugated systems toward undesired side reactions such as polymerization, isomerization, and hydrogenation. The features of these solvent-free liquid CBP derivatives make them potentially interesting for fluidic optoelectronic applications.
- Correia, Gabriel,Heinrich, Beno?t,Méry, Stéphane,Mager, Lo?c,Polychronopoulou, Kyriaki,Ribierre, Jean-Charles,Shaya, Janah
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- A Family of Superhelicenes: Easily Tunable, Chiral Nanographenes by Merging Helicity with Planar π Systems
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We designed a straightforward synthetic route towards a full-fledged family of π-extended helicenes: superhelicenes. They have two hexa-peri-hexabenzocoronenes (HBCs) in common that are connected via a central five-membered ring. By means of structurally altering this 5-membered ring, we realized a versatile library of molecular building blocks. Not only the superhelicene structure, but also their features are tuned with ease. In-depth physico-chemical characterizations served as a proof of concept thereof. The superhelicene enantiomers were separated, their circular dichroism was measured in preliminary studies and concluded with an enantiomeric assignment. Our work was rounded-off by crystal structure analyses. Mixed stacks of M- and P-isomers led to twisted molecular wires. Using such stacks, charge-carrier mobilities were calculated, giving reason to expect outstanding hole transporting properties.
- Amsharov, Konstantin Y.,B?nisch, Simon,G?rling, Andreas,Guldi, Dirk M.,Haines, Philipp,Hampel, Frank,Jelfs, Kim E.,Jux, Norbert,Nelson, Jenny,Reger, David,Schmidt, Julia A.,Ullrich, Tobias
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supporting information
p. 18073 - 18081
(2021/07/16)
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- A nitrophenyl-carbazole based push-pull linker as a building block for non-linear optical active coordination polymers: A structural and photophysical study
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Non-linear optical effects (NLO) such as multi-photon absorption, second harmonic generation (SHG) etc. have a wide range of applications. Nevertheless, the performance of many NLO-active organic dyes is limited by their thermal stability and photobleaching. These problems can be overcome by integrating the dyes into coordination polymers or metal-organic frameworks. Here, we present a structural and photophysical study of dipropyl-9-(4-nitrophenyl)-carbazole-3,6-dicarboxylate, a new “push-pull” organic dye molecule designed as a chromophore linker for NLO-active coordination polymers. Structure determination of a single-crystal showed that it crystallizes in a monoclinic crystal system P 21/c. The solvated chromophore exhibits two aromatic absorption bands at 250 nm and 275 nm as well as broad long wavelength band at 350 nm, which we assign to an intramolecular charge transfer state. Photoluminescence measurements in solvents of different polarities revealed two main effects: In nonpolar solvents, the spectrum shows an emission band at 360 nm, whereas in solvents with a higher polarity, the emission maximum broadens and redshifts. Solid-state emission measurement of sample powder exhibits an emission band at 520 nm which is redshifted compared to the measurements in solution, due to excimer formation in the solid-state. The optical as well as solvation-related properties of the investigated pigment render it to be a versatile ligand in coordination polymers.
- Fischer, Roland A.,Hauer, Jürgen,Mayer, David C.,P?thig, Alexander,Thyrhaug, Erling,Weish?upl, Sebastian J.
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- Pyridazine–carbazole based fluorescent probes for volatile acid detection
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Stimuli-responsive materials based on donor–acceptor systems have great potential for sensing applications, including in the solid state. Herein, two push–pull-type molecules, 3,6-di(9H-carbazol-9-yl)pyridazine (CzPyr–H) and 3,6-bis(3,6-dimethoxy-9H-carbazol-9-yl)pyridazine (CzPyr–OMe), each of which contain two carbazole donors and a pyridazine acceptor, were designed and synthesized. The photophysical properties of CzPyr–H and CzPyr–OMe were systematically explored with the aim of switching the absorption and emission properties using trifluoroacetic acid (TFA) as an external analyte, thus realizing volatile acid sensing. The protonation of the central pyridazine unit led to a broad absorption band at longer wavelengths owing to intramolecular charge transfer (ICT), and the emission intensity gradually decreased with increasing TFA concentration. Density functional theory calculations of the HOMO–LUMO energy gaps and orbital distributions of CzPyr–H and CzPyr–OMe as well as their protonated forms, CzPyr–H(H+) and CzPyr–OMe(H+), confirmed that charge transfer occurred in the protonated species. In their aggregated solid states, both compounds showed interesting emission properties including aggregation-enhanced emission (AEE). Utilizing their TFA sensitivity and the AEE phenomenon, CzPyr–H and CzPyr–OMe were successfully applied as fluorescent probes for volatile acid detection and as security ink for information encryption on paper.
- Han, Won-Sik,Kim, Seung-Hwan,Lee, Sohee,Lee, Sunhee,Lee, Yeeun,Lee, Yong Sup,Wang, Kang-Kyun,Yang, Kwang-Hwan
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- A star-shaped cyclopentadithiophene-based dopant-free hole-transport material for high-performance perovskite solar cells
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A new cyclopentadithiophene (CPDT)-based organic small molecule serves as an efficient dopant-free hole transport material (HTM) for perovskite solar cells (PSCs). Upon incorporation of two carbazole groups, the resulting CPDT-based HTM (C-CPDT) shows an impressive power conversion efficiency (PCE) of 19.68% with better stability compared with those of spiro-OMeTAD.
- Abate, Seid Yimer,Lai, Ping-Sheng,Lee, Kun-Mu,Liau, Kang-Ling,Lin, Yan-Duo,Luo, Ke-Jyun,Yang, Jui-Yu,Yang, Ting-Yu
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supporting information
p. 6444 - 6447
(2021/07/02)
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- Carbazole- And thiophene-containing conjugated microporous polymers with different planarity for enhanced photocatalytic hydrogen evolution
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We report the synthesis of two carbazole-thiophene-based conjugated microporous polymers (Cz-3Th and Cz-4Th CMPs) with different degrees of planarity for photocatalytic hydrogen evolution from water. Depending upon the building linker's planarity, we found that the porous structure, hydrogen-evolution rate, and photocatalytic stability of the resultant CMPs varied.
- Lee, Tsung-Lin,Elewa, Ahmed M.,Kotp, Mohammed G.,Chou, Ho-Hsiu,El-Mahdy, Ahmed F. M.
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supporting information
p. 11968 - 11971
(2021/11/30)
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- Predictable site-selective functionalization: Promoter group assistedpara-halogenation ofN-substituted(hetero)aromatics under metal-free condition
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Herein, regioselectivepara-C-H halogenation ofN-pyrimidyl (hetero)aromatics through SEAr (electrophilic aromatic substitution) type reaction is disclosed. SEAr type reaction has been utilized for the C5-bromination of indolines (para-selective) withN-bromosuccinimide under metal and additive-free conditions in good to excellent yields. The developed methodology is also applicable for iodination and challenging chlorination. The pyrimidyl group is identified as a reactivity tuner that also controls the regioselectivity. The present method is also applicable for selective halogenation of aniline, pyridine, indole, oxindole, pyrazole, tetrahydroquinoline, isoquinoline, and carbazole. DFT studies such as Fukui nucleophilicity and natural charge maps also support the observedp-selectivity. Post-functionalization of the title compound into the corresponding arylated, olefinated, and dihalogenated products is achieved in a one-pot, two-step fashion. Late-stage C-H bromination was also executed on drug/natural molecules (harmine, etoricoxib, clonidine, and chlorzoxazone) to demonstrate the applicability of the developed protocol.
- Gupta, Shiv Shankar,Manisha,Kumar, Rakesh,Dhiman, Ankit Kumar,Sharma, Upendra
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p. 9675 - 9687
(2021/12/01)
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- Utilization of conformation change and charge trapping to achieve binary/ternary rewritable memory performance of carbazole-based organic molecules
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To better understand the relationship between the molecular structure and memory characteristics, two carbazole-based organic compounds (Cz-2Ph3F 6FDA and Cz-2TPA 6FDA) with different ratios of electron-donating and electron-withdrawing units were designed and synthesized. An ITO/Cz-2Ph3F 6FDA/Al device was fabricated and presented binary rewritable memory behavior, whereas the as-fabricated ITO/Cz-2TPA 6FDA/Al device exhibited ternary rewritable memory behavior. The electrical conduction behaviors of memory devices were analyzed through theoretical models and experimental data. The molecular simulation indicated that the electrical switching behaviors could be caused by field-induced charge transfer in combination with a conformation change and charge traps. This study provide a practicable strategy to acquired organic molecules with high-performance memory characteristics. This journal is
- Gou, Gaozhang,He, Xiujuan,Liu, Juqing,Ma, Jinwen,Mao, Huiwu,Yang, Yanhua
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p. 22629 - 22638
(2021/12/24)
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- N,N′-bicarbazole-benzothiadiazole-based conjugated porous organic polymer for reactive oxygen species generation in live cells
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A π-conjugated porous organic polymer (BCzBz) was fabricated employingN,N′-bicarbazole and benzothiadiazole as molecular building units exhibiting broad visible light absorption. The photostable, water-dispersible, and cytocompatible BCzBz was demonstrated as an efficient probe for intracellular reactive oxygen species generation under photoirradiation.
- Behera, Biswajit,Giri, Arkaprabha,Kundu, Subhankar,Patra, Abhijit,Saha, Nitu
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supporting information
p. 6875 - 6878
(2021/07/19)
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- Symmetry-Guided Synthesis of N,N′-Bicarbazole and Porphyrin-Based Mixed-Ligand Metal-Organic Frameworks: Light Harvesting and Energy Transfer
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In the past decades, many attempts have been made to mimic the energy transfer (EnT) in photosynthesis, a key process occurring in nature that is of fundamental significance in solar fuels and sustainable energy. Metal-organic frameworks (MOFs), an emerging class of porous crystalline materials self-assembled from organic linkers and metal or metal cluster nodes, offer an ideal platform for the exploration of directional EnT phenomena. However, placing energy donor and acceptor moieties within the same framework with an atomistic precision appears to be a major synthesis challenge. In this work, we report the design and synthesis of a highly porous and photoactive N,N′-bicarbazole- and porphyrin-based mixed-ligand MOF, namely, NPF-500-H2TCPP (NPF = Nebraska porous framework; H2TCPP = meso-tetrakis(4-carboxyphenyl)porphyrin), where the secondary ligand H2TCPP is incorporated precisely through the open metal sites of the equatorial plane of the octahedron cage resulting from the underlying (4,8) connected network of NPF-500. The efficient EnT process from N,N′-bicarbazole to porphyrin in NPF-500-H2TCPP was captured by time-resolved spectroscopy and exemplified by photocatalytic oxidation of thioanisole. These results demonstrate not only the capability of NPF-500 as the scaffold to precisely arrange the donor-acceptor assembly for the EnT process but also the potential to directly utilize the EnT process for photocatalytic applications.
- Fiankor, Christian,Hu, Yuchen,Huang, Jier,Khoo, Rebecca Shu Hui,Nyakuchena, James,Yang, Sizhuo,Zhang, Jian,Zhang, Xu
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supporting information
p. 20411 - 20418
(2021/12/03)
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- Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties
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Two novel carbazole-based compounds 7a and 7b were synthesised as potential candidates for application in organic electronics. The materials were fully characterised by NMR spectroscopy, mass spectrometry, FTIR, thermogravimetric analysis, differential scanning calorimetry, cyclic voltammetry, and absorption and emission spectroscopy. Compounds 7a and 7b, both of which were amorphous solids, were stable up to 291 °C and 307 °C, respectively. Compounds 7a and 7b show three distinctive absorption bands: high and mid energy bands due to locally excited (LE) transitions and low energy bands due to intramolecular charge transfer (ICT) transitions. In dichloromethane solutions compounds 7a and 7b gave emission maxima at 561 nm and 482 nm with quantum efficiencies of 5.4% and 97.4% ± 10%, respectively. At positive potential, compounds 7a and 7b gave two different oxidation peaks, respectively: quasi-reversible at 0.55 V and 0.71 V, and reversible at 0.84 V and 0.99 V. At negative potentials, compounds 7a and 7b only exhibited an irreversible reduction peak at -1.86 V and -1.93 V, respectively.
- Altinolcek, Nuray,Battal, Ahmet,Peveler, William J.,Skabara, Peter J.,Tavasli, Mustafa,Yu, Holly A.
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p. 1066 - 1074
(2020/07/04)
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- One-pot synthesis of a white-light emissive bichromophore operated by aggregation-induced dual emission (AIDE) and partial energy transfer
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Merocyanine-triarylamine bichromophores are readily synthesized by sequentially Pd-catalyzed insertion-alkynylation-Michael-Suzuki four-component reactions. White-light emissive systems form upon aggregation in 1 : 99 and 0.1 : 99.9 vol percent CH2Cl2-cyclohexane mixtures, ascribed to aggregation-induced dual emission (AIDE) in combination with partial energy transfer between both chromophore units as supported by spectroscopic studies.
- Biesen, Lukas,Deni?en, Melanie,Hannen, Ricarda,Hoffmann, Katrin,Itskalov, Dana,Müller, Thomas J. J.,Nirmalananthan-Budau, Nithiya,Reiss, Guido J.,Resch-Genger, Ute
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supporting information
p. 7407 - 7410
(2020/07/15)
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- Minimization of Carrier Losses for Efficient Perovskite Solar Cells through Structural Modification of Triphenylamine Derivatives
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Three hole transport materials (HTMs) based on a substituted triphenylamine moiety have been synthesized and successfully employed in triple-cation mixed-halide PSCs, reaching efficiencies of 19.4 %. The efficiencies, comparable to those obtained using spiro-OMeTAD, point them out as promising candidates for easily attainable and cost-effective alternatives for PSCs, given their facile synthesis from commercially available materials. Interestingly, although all these HTMs show similar chemical and physical properties, they provide different carrier recombination kinetics. Our results demonstrate that is feasible through the molecular design of the HTM to minimize carrier losses and, thus, increase the solar cell efficiencies.
- Méndez, Maria,Nazeeruddin, Mohammad Khaja,Palomares, Emilio Jose,Pudi, Ravi,Rodríguez-Seco, Cristina,Roldán-Carmona, Cristina
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supporting information
p. 5303 - 5307
(2020/02/15)
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- A highly fluorescent covalent organic framework as a hydrogen chloride sensor: roles of Schiff base bonding and π-stacking
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In this paper we report the extremely crystalline structures, high thermal stabilities, and strong fluorescence emissions of covalent organic frameworks (COFs) based on linked carbazole units. We have synthesized three stable luminescent carbazole-linked COFs, namely, BCTB-PD, BCTA-TP, and BCTB-BCTA, through Schiff base condensations of 4,4′,4′′,4′′′-([9,9′-bicarbazole]-3,3′,6,6′-tetrayl)tetrabenzaldehyde (BCTB-4CHO) with p-phenylenediamine (PD), of 4,4′,4′′,4′′′-([9,9′-bicarbazole]-3,3′,6,6′-tetrayl)tetraaniline (BCTA-4NH2) with terephthalaldehyde (TP), and of BCTB-4CHO with BCTA-4NH2, respectively. These COFs had large Brunauer-Emmett-Teller surface areas (up to 2212 m2 g-1) and outstanding thermal stabilities (decomposition temperatures of up to 566 °C). Interestingly, the intramolecular charge transfer (ICT) and fluorescence properties of these COFs were strongly influenced by their types of Schiff base bonding (BCTB-4CHN or BCTA-4NCH) and the degrees of π-stacking between their COF layers. For example, ICT from the electron-donating carbazole group to the acceptor through the Schiff base units of the type BCTB-4CHN and increasing the π-stacking distance enhanced the fluorescence emission from the COF. Moreover, BCTB-BCTA, the most fluorescent of our three COFs, functioned as a fluorescent chemosensor for HCl in solution, with outstanding sensitivity and a rapid response. This journal is
- El-Mahdy, Ahmed F. M.,Kuo, Shiao-Wei,Lai, Ming-Yi
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supporting information
p. 9520 - 9528
(2020/08/17)
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- Heteroporous bifluorenylidene-based covalent organic frameworks displaying exceptional dye adsorption behavior and high energy storage
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In this study we performed one-pot polycondensations of BFTB-4CHO with PyTA-4NH2, BFTB-4NH2, and BCTA-4NH2 to prepare the bifluorenylidene-based covalent organic frameworks (COFs) BFTB-PyTA, BFTB-BFTB, and BFTB-BCTA, respectively. These three COFs possessed extremely high thermal stabilities, excellent crystallinities, and high specific surface areas. The BFTB-PyTA COF featured pores of a single size, whereas the BFTB-BFTB and BFTB-BCTA COFs had dual porosities. The COFs were exceptional adsorbers of the small dye molecule rhodamine B (RhB) in water; the maximum adsorption capacities reached as high as 2127 mg g-1, outpacing those of all previously reported COFs, conjugated polymers, activated carbons, and other common nanoporous adsorbents. In addition, our COFs reached up to 99.2% of their maximum adsorption capabilities very rapidly (within 5 min). Furthermore, these COFs displayed good performance when used in electrodes for supercapacitors, with high stability after 2000 cycles. The superior adsorption efficiencies, ultrafast kinetics, and excellent reusability endow such COFs with tremendous potential for use as materials for removing RhB-and, presumably, other organic pollutants-from wastewater.
- Chen, Tao,El-Mahdy, Ahmed F. M.,Kuo, Shiao-Wei,Wang, Hao-Xin,Yamauchi, Yusuke,Zakaria, Mohamed Barakat
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supporting information
p. 25148 - 25155
(2020/12/23)
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND A ELECTRONIC DEVICE THEREOF
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The present invention relates to a novel compound, an organic electric element using the same, and an electronic device thereof. According to the present invention, a luminous efficiency, a color purity and a lifespan of the element can be improved and a driving voltage can be lowered. The organic electric element comprises: an anode; a cathode; and an organic material layer formed between the anode and the cathode.
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Paragraph 0134; 0136-0139
(2020/05/30)
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- CARBAZOLE AND ACRIDINE PHOTOREDOX CATALYSTS FOR SMALL MOLECULE AND MACROMOLECULAR TRANSFORMATIONS
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The present invention provides photocatalysts, methods for their preparation, and methods for preparing linear polymers with high propagation rate.
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Paragraph 00135
(2020/10/20)
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- Exploitation of two-dimensional conjugated covalent organic frameworks based on tetraphenylethylene with bicarbazole and pyrene units and applications in perovskite solar cells
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In this work, two-dimensional conjugated covalent organic frameworks (2D-COF) based on a building block of tetraphenylethylene are successfully developed. Bicarbazole and pyrene moieties are respectively coupled with 4,4′,4′′,4′′′-(ethane-1,1,2,2-tetrayl)tetranilino (ETTA)via[4 + 4] solvothermal condensation conditions of 3,3′,6,6′-tetraformyl-9,9′-bicarbazole (Car-4CHO) and 1,3,6,8-tetrakis(4-formylphenyl)pyrene (TFPPy) to affordCar-ETTAandTFPPy-ETTACOFs. According to thermogravimetric analysis (TGA), powder X-ray diffraction (PXRD), and N2adsorption and desorption measurements, bothCar-ETTAandTFPPy-ETTACOFs exhibit excellent thermal stability, highly crystalline structure, and high specific surface area, respectively. These findings are supported by force field andab initiocalculations. Furthermore, successful applications of these COFs in perovskite solar cells (PVSCs) are demonstrated owing to their well-conjugated properties and π-π interactions. While serving as interlayers in the devices, these COFs could effectively promote the interfacial charge dynamic to further optimize the resulting performance. Besides, certain interaction between COFs and perovskite also leads to an improved morphology and crystallinity of the perovskite layer, presenting defect passivation capability. As a result, we show that the performance of the COF-modified PVSC could be improved from 17.40 to 19.80%.
- Chueh, Chu-Chen,EL-Mahdy, Ahmed F. M.,Kuo, Shiao-Wei,Lüder, Johann,Lee, Chia-Chen,Li, Zhen,Mohamed, Mohamed Gamal,Yu, Ming-Hsuan,Zhu, Zonglong
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supporting information
p. 11448 - 11459
(2020/06/17)
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- 1,2,3-Triazolyl functionalized thiophene, carbazole and fluorene based A-: Alt -B type π-conjugated copolymers for the sensitive and selective detection of aqueous and vapor phase nitroaromatics (NACs)
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A series of highly emissive π-conjugated A-alt-B type copolymers (P1-P3) appended with a 1,2,3-triazole moiety was synthesized via Suzuki polymerization. The well-defined and soluble π-conjugated copolymers were characterized via multinuclear NMR spectroscopy and tetradetector GPC studies, showing a molecular weight (Mn) in the range of 16.4-20.1 kDa with a polydispersity index in the range of 1.25-1.42. The synthesized emissive π-conjugated polymer probes were explored as fluorescent chemosensors for nitroaromatic compounds (NACs) in solution, vapor and contact mode. Detailed photophysical and sensing studies were performed to understand the polymer-NAC interaction, inducing the selective fluorescence quenching of the π-conjugated polymer probes through the photoinduced electron transfer (PET) mechanism. All the polymeric probes (P1-P3) were highly reversible in nature with NACs, and thus could be reused multiple times. The limit of detection of the probes towards nitroaromatics was found to be in the range of 120-200 ppb with a high association constant in the order of 104 M-1. Furthermore, test paper kits were also fabricated, which allowed the trace detection of picric acid by the naked eye, making it a practical means for the quick, easy and inexpensive on-site detection of NAC-based explosives.
- Giri, Dipanjan,Patra, Sanjib K.
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supporting information
p. 14469 - 14480
(2020/11/09)
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- Reversible switching between positive and negative thermal expansion in a metal-organic framework DUT-49
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Three-dimensional architectures constructed via coordination of organic ligands to metal ions (broadly termed metal-organic frameworks, MOFs), are highly interesting for many demanding applications such as gas adsorption, molecular separation, heterogeneous catalysis, molecular sensing, etc. Being constructed from heterogeneous components, such framework solids show characteristic features from both the individual components and framework-specific features. One such interesting physicochemical property is thermal expansion, which arises from thermal vibration from the organic linker and metal ions. Herein, we show a very unique example of thermal responsiveness for the DUT-49 framework, a MOF well-known for its distinctive negative gas adsorption (NGA) properties. In the guest-free form, the framework shows another counter-intuitive phenomenon of negative thermal expansion (NTE), i.e. the lattice size increases with decrease of temperature. However, in the solvated state, it shows both NTE and positive thermal expansion (i.e. lattice size decreases with lowering of temperature, PTE) based on a specific temperature range. When the solvent exists in the liquid form inside the MOF pore, it retains the pristine NTE nature of the bare framework. But freezing of the solvent inside the pores induces the strain, which causes a structural transformation through in-plane bending of the linker and this squeezes the framework by ～10% of the unit cell volume. This effect has been verified using 3 different solvents where the structural contraction occurs immediately at the freezing point of the individual solvent. Furthermore, studies on a series of DUT-49(M) frameworks with varying metals confirm the general applicability of this mechanism.
- Bon, Volodymyr,Efimova, Anastasia,Garai, Bikash,Gerlach, Martin,Kaskel, Stefan,Senkovska, Irena
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supporting information
p. 20420 - 20428
(2020/11/04)
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- Photo-induced phosphorescence and mechanoluminescence switching in a simple purely organic molecule
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A simple organic molecule, 2-(9H-carbazol-9-yl)ethanol (CZEO), displays both mechanoluminescence (ML) and photo-induced room-temperature phosphorescence (RTP). The D-A type dimer formed in the crystals was found to play a crucial role in the light-stimulated luminescent response, responsible for the turn-on RTP and turn-off ML switching of CZEO.
- Huang, Qiuqin,Mei, Xiaofei,Xie, Zongliang,Wu, Duobin,Yang, Shuming,Gong, Wenjing,Chi, Zhenguo,Lin, Zhenghuan,Ling, Qidan
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supporting information
p. 2530 - 2534
(2019/03/08)
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- A New Biscarbazole-Based Metal–Organic Framework for Efficient Host–Guest Energy Transfer
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A new metal–organic framework (MOF), [Zn6L4(Me2NH2+)4?3 H2O] (1) was constructed based on [9, 9′-biscarbazole]-3, 3′, 6, 6′-tetracarboxylic acid (H4L) and Zn2+ ions. The porous framework and intense blue fluorescence of the MOF based on the biscarbazole moiety of the ligand could facilitate efficient host to guest energy transfer, which makes it an ideal platform for the tuning of luminescence.
- Mu, Qianqian,Liu, Jingjuan,Chen, Weiben,Song, Xiaoyu,Liu, Xiaoting,Zhang, Xiaotao,Chang, Ze,Chen, Long
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supporting information
p. 1901 - 1905
(2019/01/11)
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- Methoxy- and tert-butyl-substituted meta-bis(N-carbazolyl)phenylenes as hosts for organic light-emitting diodes
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Two new analogues of a popular host material, meta-bis(N-carbazolyl)phenylene (mCP), bearing either methoxy- (mCP-OMe) or tert-butyl (mCP-t-Bu) substituents at C-3 and C-6 positions of carbazole moieties were synthesized and characterized. These materials exhibit higher glass-transition temperatures (79 and 145 °C) than mCP (67 °C). They show reversibility upon electrochemical oxidation while preserving high enough triplet energy levels (2.86 and 2.97 eV). The vacuum-deposited layer of mCP-t-Bu showed hole mobility of 8 × 10?3 cm2V?1s?1 at the electric field of 1.2 × 105 Vcm?1. This value is more than by one order of magnitude higher than that of mCP. The new compounds were tested as hosts for commercial emitters: blue phosphor, bis[2-(4,6-difluorophenyl)pyridinato-C2,N](picolinato)iridium(III) (FIrpic), green and blue thermally-activated delayed fluorescence (TADF) emitters 1,2,3,5-tetrakis(9-carbazolyl)-4,6-dicyanobenzene (4CzIPN) and bis[4-(9,9-dimethyl-9,10-dihydroacridin-10-yl)phenyl]sulfone (DMAC-DPS). Blue phosphorescent OLED based on mCP-t-Bu as the host showed up to 22.0% external quantum efficiency. When doping 4CzIPN into mCP-OMe host, a broad emission with peaks at 388, 514, and 572 nm was observed.
- Keruckas, Jonas,Volyniuk, Dmytro,Simokaitiene, Jurate,Narbutaitis, Edgaras,Lazauskas, Algirdas,Lee, Pei-Hsi,Chiu, Tien-Lung,Lin, Chi-Feng,Arsenyan, Pavel,Lee, Jiun-Haw,Grazulevicius, Juozas V.
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p. 317 - 326
(2019/07/02)
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- Direct Synthesis of Microporous Bicarbazole-Based Covalent Triazine Frameworks for High-Performance Energy Storage and Carbon Dioxide Uptake
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In this study a series of bicarbazole-based covalent triazine frameworks (Car-CTFs) were synthesized under ionothermal conditions from [9,9'-bicarbazole]-3,3',6,6'-tetracarbonitrile (Car-4CN) in the presence of molten zinc chloride. Thermogravimetric and Brunauer?Emmett?Teller analyses revealed that these Car-CTFs possessed excellent thermal stabilities and high specific surface areas (ca. 1400 m2/g). The electrochemical performances of this Car-CTF series, investigated by using cyclic voltammetry, showed a highest capacitance of (545 F/g at 5 mV/s), which also exhibited excellent columbic efficiencies of 96.1 % after 8000 cycles at 100 μA/0.5 cm2. The other Car-CTF samples displayed similar efficiencies. Furthermore, based on CO2 uptake measurements, one of the series showed the highest CO2 uptake capacities: 3.91 and 7.60 mmol/g at 298 and 273 K, respectively. These results suggest a simple method for the preparation of CTF materials that provide excellent electrochemical and CO2 uptake performance.
- Mohamed, Mohamed Gamal,EL-Mahdy, Ahmed F. M.,Ahmed, Mahmoud M. M.,Kuo, Shiao-Wei
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p. 1767 - 1774
(2019/12/02)
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- Diversity of metal-organic macrocycles assembled from carbazole based ligands with different lengths
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A series of carbazole based ligands with different lengths were assembled with nickel ions to construct metal-organic macrocycles. High-resolution mass spectrometry and ion mobility-mass spectrometry have been used to analyse the resulting MnLn assembly coexisting in solution. Combining with the structural analysis of their solid confirmation, it was revealed that the diversity of the metal-organic macrocycles was increased with the flexibility of the ligands.
- Yu, Hao,Wang, Jing,Guo, Xiangyang,Zhang, Rong,He, Cheng,Duan, Chunying
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supporting information
p. 4040 - 4044
(2018/03/26)
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- Novel carbazole derivatives and organic light emitting device comprising the same
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Provided are a novel compound and an organic light emitting device comprising the same. The compound is represented by chemical formula 1. The abovementioned compound represented by the chemical formula 1 can be used as a material for an organic material layer of an organic light emitting device, for improving the efficiency, the low driving voltage and/or the lifetime characteristics in the organic light emitting device.COPYRIGHT KIPO 2018
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Paragraph 0157-0160
(2018/08/22)
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- Electroluminescent polymeric monomer, electroluminescent polymer as well as preparation method and application of electroluminescent polymer
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The invention belongs to the technical field of organic optoelectronics and discloses an electroluminescent polymeric monomer, an electroluminescent polymer as well as a preparation method and an application of the electroluminescent polymer. The structural formula of the polymeric monomer M1 is shown in the description, and the polymeric monomer M1 contains boron and nitrogen heteroatoms. Boron atoms have unoccupied Ppi orbit in the center and can accept electrons as Lewis acid, boron is in key joint with an aromatic ring substituent, P-pi conjugation is formed, the conjugation degree is increased, so that fluorescence of the monomer M1 is enhanced, and fluorescence quantum yield of a luminescent material is increased; the monomer M1 is endowed with better hole transport capability by a pair of lone pair electrons of nitrogen atoms. The monomer M1 is of a multi-condensed ring structure, and the carrier transport capability of the material can be improved by means of larger conjugate plane. The electroluminescent polymer contains repeat units derived from the electroluminescent polymeric monomer M1, has better solubility, can be dissolved with a common organic solvent and can forma film by spin coating, ink-jet printing or printing, and a luminescent layer of an LED is prepared.
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Paragraph 0093-0095
(2019/09/21)
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- A carbazole compound and use thereof (by machine translation)
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The invention discloses a carbazole compound and its use. The carbazole compound of the formula (I) has a structure shown in: Formula (I) in which: R1 For C1 - C12 Hydrocarbyl or C1 - C12 C alkoxy or4 - C20 Heterocyclic radical, wherein said heterocyclic group or hetero atom as the N S or O; R2 For C1 - C12 Hydrocarbyl; R3 Is aromatic hydrocarbyl or heterocyclic aromatic hydrocarbyl. The invention said compound can be used as a dye-sensitized solar cell of the sensitizer. (by machine translation)
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Paragraph 0027-0029
(2018/03/24)
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- Poly(benzodithieno-imidazole-alt-carbazole) based π-conjugated copolymers: Highly selective and sensitive turn-off fluorescent probes for Hg2+
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In this work, highly emissive and soluble π-conjugated poly(benzodithieno-imidazole-alt-carbazole) π-conjugated copolymers (P1 and P2) have been synthesized through Pd(0)-catalyzed Suzuki coupling polymerization protocol from the corresponding monomers. For solubilizing in common organic solvents, heptyl (in P1) or 2-(2-(2-methoxyethoxy)ethoxy)ethyl (in P2) substituents have been introduced at benzodithieno-imidazole and 9-position of carbazole unit. The well-defined and soluble π-conjugated polymers have been characterized by multinuclear NMR spectra as well as by tetradetector GPC studies showing molecular weight (Mn) of 16.5 and 14.3 kDa with the polydispersity indices of 1.36 and 1.31 respectively. The emissive π-conjugated polymers show remarkable selectivity and sensitivity towards Hg2+ ion as turn-off fluorescent probes as a result of molecular wire effect, without interference by other competing metal ions. The detailed photophysical and sensing studies have been demonstrated to understand the insight of polymer-metal ion interaction which is responsible for selective fluorescence quenching of the π-conjugated polymers. DFT studies have been performed to gain the insight of the electronic properties of the sensor by determining the frontier molecular orbitals and the HOMO-LUMO energy levels for a model probe (M1). The polymeric probes (P1 and P2) are reversible in nature, and can also act as secondary sensors for S2-. The limit of detection of the polymer probes towards Hg2+ is found to be in the range of 40–50 ppb with high association constant in the order of 105 M?1 suggesting its high applicability as chemosensor for Hg2+. The polymers have also been explored as thin film polymeric sensor towards Hg2+ to demonstrate its practical utility.
- Giri, Dipanjan,Bankura, Arindam,Patra, Sanjib K.
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p. 338 - 353
(2018/11/30)
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- Dialkyl-substituted naphtho-dioxodibenzothiophene monomer and preparation method thereof and polymer containing dialkyl-substituted naphtho-dioxodibenzothiophene unit and application of polymer
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The invention discloses a dialkyl-substituted naphtho-dioxodibenzothiophene monomer and a preparation method thereof and a polymer containing a dialkyl-substituted naphtho-dioxodibenzothiophene unit and the application of the polymer. A high-absorption electron unit -SO2- exists in the dialkyl-substituted naphtho-dioxodibenzothiophene monomer, and thus the electron affinity of a molecule can be improved. Through introducing of an unsymmetrical substituting condensed ring structure and an alkyl group, the electron affinity of the monomer can be lowered, and meanwhile, solubleness of the monomer in organic solvent is improved greatly. The dialkyl-substituted naphtho-dioxodibenzothiophene monomer obtains a homopolymer or a copolymer containing the dialkyl-substituted naphtho-dioxodibenzothiophene unit through Suzuki or Stille or Yamamoto polymerization reaction, and the obtained polymer has good solubleness in the organic solvent, is suitable for solution processing, and has wide application prospects in preparation of electroluminescent devices, organic solar cells and organic field effect transistors.
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Paragraph 0057; 0058; 0059; 0060
(2017/08/28)
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- Bicarbazole-based redox-active covalent organic frameworks for ultrahigh-performance energy storage
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A highly redox-active building block, bicarbazole, is developed as a monomer for designing crystalline porous covalent organic frameworks and is successfully integrated to the vertices of microporous tetragonal frameworks, leading to densely aligned redox-active arrays. The frameworks with large porosity and high accessibility of the redox-active sites exhibit synergistic structural effects and ultrahigh-performance energy storage.
- Feng, Shi,Xu, Hong,Zhang, Chong,Chen, Yu,Zeng, Jinghui,Jiang, Donglin,Jiang, Jia-Xing
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supporting information
p. 11334 - 11337
(2017/10/19)
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- Studies on the Enantioselective Iminium Ion Trapping of Radicals Triggered by an Electron-Relay Mechanism
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A combination of electrochemical, spectroscopic, computational, and kinetic studies has been used to elucidate the key mechanistic aspects of the previously reported enantioselective iminium ion trapping of photochemically generated carbon-centered radicals. The process, which provides a direct way to forge quaternary stereocenters with high fidelity, relies on the interplay of two distinct catalytic cycles: the aminocatalytic electron-relay system, which triggers the stereoselective radical trap upon iminium ion formation, and the photoredox cycle, which generates radicals under mild conditions. Critical to reaction development was the use of a chiral amine catalyst, bearing a redox-active carbazole unit, which could rapidly reduce the highly reactive and unstable intermediate generated upon radical interception. The carbazole unit, however, is also involved in another step of the electron-relay mechanism: the transiently generated carbazole radical cation acts as an oxidant to return the photocatalyst into the original state. By means of kinetic and spectroscopic studies, we have identified the last redox event as being the turnover-limiting step of the overall process. This mechanistic framework is corroborated by the linear correlation between the reaction rate and the reduction potential of the carbazole unit tethered to the aminocatalyst. The redox properties of the carbazole unit can thus be rationally tuned to improve catalytic activity. This knowledge may open a path for the mechanistically driven design of the next generation of electron-relay catalysts.
- Bahamonde, Ana,Murphy, John J.,Savarese, Marika,Brémond, éric,Cavalli, Andrea,Melchiorre, Paolo
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supporting information
p. 4559 - 4567
(2017/04/04)
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- Easy accessible blue luminescent carbazole-based materials for organic light-emitting diodes
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The thermal, optical, electrochemical and charge transport properties of a series of nine straightforward carbazole-based compounds have been analysed and interpreted according to their molecular structure by means of the X-ray analysis of single crystals. A non-doped OLED device with low turn-on voltage and maximum luminance up to 1.4 × 104 cd m?2 was achieved. DFT calculations have been performed to explain the high efficiency of radiative exciton production.
- Reig, Marta,Gozálvez, Cristian,Bujaldón, Roger,Bagdziunas, Gintautas,Ivaniuk, Khrystyna,Kostiv, Nataliya,Volyniuk, Dmytro,Grazulevicius, Juozas V.,Velasco, Dolores
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- Synthesis and properties of photocross-linkable carbazole dimers
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New carbazole-based monomers with two reactive functional groups such as epoxypropyl, oxetanyl and vinyloxethyl were synthesized and their cationic photopolymerization was performed. The monomer containing epoxypropyl groups exhibited the highest conversion in photopolymerization (78%). The monomers and polymers exhibited ability of glass formation with the glass transition temperatures up to 98?°C for low-molecular-weight compounds and those observed for polymers ranging from 89 to 150?°C. The synthesized derivatives absorb electromagnetic irradiation in the range of 200–390?nm with the band gaps of 3.14–3.16?eV. The compounds exhibit blue photoluminescence with the intensity maxima at 400?nm. The compounds were found to have high triplet energies of ca. 2.78?eV. The electron photoemission spectra of the layers of the synthesized compounds revealed ionization potentials of 5.20–5.37?eV. The time-of-flight hole drift mobilities of the layers of the compounds exceed 10??5?cm2/V?×?s at high electric fields.
- Simkus,Tomkeviciene,Volyniuk,Kostjuk,Grazulevicius
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- Synthesis of novel styryl-: N -isopropyl-9 H -carbazoles for designing trans -conjugated regular silicon hybrid materials
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An efficient synthesis and characterization of several new, conjugated styryl-carbazole compounds functionalized by monovinylsilanes in a stereocontrolled approach is presented. All N-organic derivatives were successfully examined in silylative coupling in the presence of ruthenium-hydride complexes 4 and 5. Furthermore, a novel class of vinylene-arylene linear oligomeric materials with 1,4-bis(dimethylvinylsilyl)naphthalene in the main chain was produced. Both reactions proceed very effectively, stereo- and regioselectively, allowing one to obtain E-isomer derivatives with high isolation yields.
- Majchrzak, Mariusz,Grzelak, Magdalena,Marciniec, Bogdan
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supporting information
p. 9406 - 9415
(2016/10/13)
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- Preparation method of high-purity 3,6-dibromo-carbazole
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The present invention discloses a preparation method of high-purity 3,6-dibromo-carbazole. The preparation method comprises the following steps: carbazole and absolute ethyl alcohol are added into a container, and dibromodimethyl hydantoin is added into the container in batches at room temperature; a reaction is stopped until no monobromination product is detected by HPLC spectrum; and crude products can be obtained by a direct filtration; and the crude products are subjected to hot ethanol reflux, cooling treatment and additional filtration, thereby obtaining white crystalline solid products. The preparation method uses the absolute ethyl alcohol as a solvent, improves the production and operation environment, uses cheap dibromodimethyl hydantoin as a brominating agent at the same time, can synthesize the high-purity 3,6-dibromo carbazole under the condition of normal temperature, avoids bromine production, is easy to operate and control, shortens reaction time, reduces costs, and is beneficial to industrial production.
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Paragraph 0012;0013;0016
(2016/12/01)
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- A search for blues brothers: X-ray crystallographic/spectroscopic characterization of the tetraarylbenzidine cation radical as a product of aging of solid magic blue
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Magic blue (MB+? SbCl6- salt), i.e. tris-4-bromophenylamminium cation radical, is a routinely employed one-electron oxidant that slowly decomposes in the solid state upon storage to form so called 'blues brothers', which often complicate the quantitative analyses of the oxidation processes. Herein, we disclose the identity of the main 'blues brother' as the cation radical and dication of tetrakis-(4-bromophenyl)benzidine (TAB) by a combined DFT and experimental approach, including isolation of TAB+? SbCl6- and its X-ray crystallography characterization. The formation of TAB in aged magic blue samples occurs by a Scholl-type coupling of a pair of MB followed by a loss of molecular bromine. The recognition of this fact led us to the rational design and synthesis of tris(2-bromo-4-tert-butylphenyl)amine, referred to as 'blues cousin' (BC: Eox1 = 0.78 V vs. Fc/Fc+, λmax(BC+?) = 805 nm, εmax = 9930 cm-1 M-1), whose oxidative dimerization is significantly hampered by positioning the sterically demanding tert-butyl groups at the para-positions of the aryl rings. A ready two-step synthesis of BC from triphenylamine and the high stability of its cation radical (BC+?) promise that BC will serve as a ready replacement for MB and an oxidant of choice for mechanistic investigations of one-electron transfer processes in organic, inorganic, and organometallic transformations.
- Talipov, Marat R.,Hossain, Mohammad M.,Boddeda, Anitha,Thakur, Khushabu,Rathore, Rajendra
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supporting information
p. 2961 - 2968
(2016/03/12)
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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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- 1,1'9,9'-BICARBAZOLE, 1,1'-BICARBAZOLE SALT, AND PRODUCTION METHOD THEREOF
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PROBLEM TO BE SOLVED: To provide a novel 1,1',9,9'-bicarbazole compound, novel 1,1'-bicarbazole biradical salt, and a method of producing them. SOLUTION: The present invention relates to a method of producing a compound (3) by cyclizing carbazole dimers bound together at 1,1' or 9,9', and a method of producing biradical salt (4) from the compound (3). SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0071; 0072; 0073
(2016/10/08)
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- Carbazole derivative graft monomer, preparing method and application of carbazole derivative graft monomer to polyarylether polymer
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The invention provides a carbazole derivative graft monomer, a preparing method and application of the carbazole derivative graft monomer to a polyarylether polymer and belongs to the technical field of macromolecular materials and preparation thereof. The novel carbazole derivative graft monomer is named 3,6-bis(3,5-dimethyl phenyl)carbazole. The preparing process comprises the steps that 1, 3,6-dibromo-carbazole is prepared; 2, 3,6-bis(3,5-dimethyl phenyl)carbazole is obtained by means of the Suzuki coupling reaction. As carbazole and a derivative thereof have a large conjugate system, the polyaryletherketone polymer obtained by grafting has excellent heat-resisting performance and mechanical performance and has excellent performance of a photoelectric functional material, a methyl group on a side group benzene ring provides a modifiable site, obtained polyaryletherketone containing a carbazole derivative side group can be applied to multiple fields of the photoelectric material, anion-exchange membrane fuel batteries and the like.
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Paragraph 0046-0047
(2017/03/14)
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- CARBAZOLE-BASED GUMBOS FOR HIGHLY EFFICIENT BLUE OLEDS
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Various examples are provided for carbazole-based GUMBOS (group of uniform materials based on organic salts), and its application in organic light emitting diodes (OLEDs). In one example, a composition includes a solid phase carbazole-based GUMBOS (group of uniform materials based on organic salts) comprising a counterion such as, e.g., trifluoromethanesulfonate ([OTf]), bis-(trifluoromethanesulfonyl)imide ([NTf2]), bis-(pentafluoroethylsulfonyl)imide ([BETI]), tetrafluoroborate (BF4), hexafluorophosphate (PF6), and/or thiocyanate (SCN). The carbazole-based GUMBOS can include carbazoleimidazole-based GUMBOS or 3,6-diBDC carbazolium-based GUMBOS. In another example, a method includes preparing a biphasic solution; separating a layer of DCM from the biphasic solution after stirring; washing the DCM with water to remove byproducts; and evaporating the DCM to form a solid phase carbazoleimidazole-based GUMBOS. Preparing the biphasic solution can include carbazoleimidazolium iodide (CM) dissolved in dichloromethane (DCM) and a dissolved salt including a sodium salt or a lithium salt.
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Paragraph 0156
(2016/08/17)
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- One kind has electronic to the receptor structure of vinyl polymer main body material and its preparation and application method (by machine translation)
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The invention belongs to the field of photoelectric functional materials, in particular to a kind of by the electron donor group with the electron acceptor group are respectively functional modification of the PVK vinyl polymer main body material, and based on this polymer a series of optical, electrical, electrochemical performance characterization, we would be applied to the organic light-emitting field, has been succeeded in preparing a series of high-efficiency light-emitting device. Wherein the polymer material of the main body and PTPACzPO PVPPOK as an example, their traditional hole transporting material (polyvinyl carbazole) PVK as the skeleton, through a series of molecular modification, to obtain a more superior to the PVK carrier transmission performance. (by machine translation)
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Paragraph 0040; 0041; 0042
(2017/01/02)
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