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.
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.
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.
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 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.
Synthesis and characterization of 1,3,5-triphenylamine derivatives with star-shaped architecture
Brzeczek, Alina,Karon, Krzysztof,Higginbotham, Heather,J?drysiak, Rafa? G.,Lapkowski, Mieczyslaw,Walczak, Krzysztof,Golba, Sylwia
, p. 25 - 32 (2016)
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.
A fluorescent lanthanide-organic framework for highly sensitive detection of nitroaromatic explosives
Mu, Yajuan,Ran, Yungen,Du, Jianlong,Wu, Xueyi,Nie, Weiwei,Zhang, Jianhong,Zhao, Ying,Liu, Huan
, p. 125 - 130 (2017)
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.
Architectural design of new conjugated systems carrying donor-π-acceptor groups (carbazole-CF3): Characterizations, optical, photophysical properties and DSSC's applications
Caglar, Mujdat,Caglar, Yasemin,Derince, Betul,Gorgun, Kamuran
, (2021/10/27)
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.
A Family of Superhelicenes: Easily Tunable, Chiral Nanographenes by Merging Helicity with Planar π Systems
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
supporting information, p. 18073 - 18081 (2021/07/16)
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.
Pyridazine–carbazole based fluorescent probes for volatile acid detection
Han, Won-Sik,Kim, Seung-Hwan,Lee, Sohee,Lee, Sunhee,Lee, Yeeun,Lee, Yong Sup,Wang, Kang-Kyun,Yang, Kwang-Hwan
, (2021/07/06)
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.
