6825-20-3Relevant articles and documents
Synthesis and luminescent properties of novel organic luminescent materials based on carbazole derivatives
Duan, Yingxiang,Yang, Yanhua,Cen, Bo,Shen, Kecheng,Tao, Xian,Shen, Yingzhong
, p. 2955 - 2963 (2018)
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.
Syntheses, characterizations and electrochromic applications of polymers derived from carbazole containing thiophene rings in side chain with electrochemical and FeCl3 methods
Aydin, Aysel,Kaya, Ismet
, p. 730 - 743 (2013)
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.
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
Sharma,Singh, Manjeet,Kurchania, Rajnish,Koukaras,Mikroyannidis
, p. 18821 - 18834 (2013)
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.
Synthesis and characterization of red light-emitting electrophosphorescent polymers with different triplet energy main chain
Ma, Zhihua,Ding, Junqiao,Cheng, Yanxiang,Xie, Zhiyuan,Wang, Lixiang,Jing, Xiabin,Wang, Fosong
, p. 2189 - 2197 (2011)
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.
Organic dyes containing fused acenes as building blocks: Optical, electrochemical and photovoltaic properties
Gao, Peng,Tsao, Hoi Nok,Teuscher, Joel,Gr?tzel, Michael
, p. 289 - 292 (2018)
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.
Blue light-emitting polyfluorenes containing dibenzothiophene-S,S-dioxide unit in alkyl side chain
Fang, Yiwen,Liu, Jie,Zhang, Yuhao,Guo, Ting,Huang, Fei,Yang, Wei,Cao, Yong
, p. 1356 - 1366 (2017)
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.
Hydrogen-Bonded Crystalline Molecular Machines with Ultrafast Rotation and Displacive Phase Transitions
Colin-Molina, Abraham,Jellen, Marcus J.,Rodríguez-Hernández, Joelis,Cifuentes-Quintal, Miguel Eduardo,Barroso, Jorge,Toscano, Rubén A.,Merino, Gabriel,Rodríguez-Molina, Braulio
, p. 11727 - 11733 (2020)
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.
Synthesis and optical characterization of bipod carbazole derivatives
?a?ll, Merve,?i?ek, Baki,Tülek, Remziye,Teke, Ali
, p. 148 - 156 (2020)
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.
Synthesis and characterization of yellow and green light emitting novel polymers containing carbazole and electroactive moieties
Aydin, Aysel,Kaya, Ismet
, p. 104 - 114 (2012)
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.
Preparation and properties of poly[9-hexadecyl-3-phenyl-6-(4-vinylphenyl)- 9H-carbazole]
Bakiev,Shklyaeva,Lunegov,Mokrushin,Abashev
, p. 1313 - 1319 (2014)
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.
