16807-13-9Relevant articles and documents
A wet- and dry-process feasible carbazole type host for highly efficient phosphorescent OLEDs
Jou, Jwo-Huei,Sahoo, Snehasis,Kumar, Sudhir,Yu, Hui-Huan,Fang, Po-Hsun,Singh, Meenu,Krucaite, Gintare,Volyniuk, Dmytro,Grazulevicius, Juozas Vidas,Grigalevicius, Saulius
, p. 12297 - 12307 (2015)
A wet- and dry-process feasible host material is crucial to realize, respectively, low cost roll-to-roll fabrication of large area and high performance organic light-emitting diodes (OLEDs) with precise deposition of organic layers. We demonstrate in this study high efficiency phosphorescent OLED devices by employing a newly synthesized carbazole based host material 1,6-bis[3-(2-methoxy-3-pyridinyl)carbazol-9-yl]hexane (compound 5). Moreover, two other carbazole hosts 1,6-bis[3-(6-methoxy-3-pyridinyl)carbazol-9-yl]hexane (compound 4) and 3,6-di(2-methoxy-3-pyridinyl)-9-ethylcarbazole (compound 6) are also synthesized for comparison. By doping a typical green emitter fac tris(2-phenylpyridine)iridium (Ir(ppy)3) in compound 5, for example, the resultant wet-processed device exhibits at 100 cd m-2 a current efficiency of 27 cd A-1 and a power efficiency of 16.1 lm W-1. The dry-processed device shows a current efficiency of 61 cd A-1 and a power efficiency of 62.8 lm W-1. The high efficiency may be attributed to the host possessing an effective host-to-guest energy transfer, effective carrier injection balance, and the device architecture enabling excitons to generate on both the host and the guest.
Monomers and oligomers with the pendent adducts of carbazole with 5H-dibenz(b,f)azepine and its 10,11-dihydro derivative
Tomkeviciene,Bartiuk,Bucinskas,Grazulevicius,Jankauskas
, p. 796 - 802 (2011)
The synthesis of a series of carbazole-based monomers incorporating dibenzazepines at the 3 position is reported. Full characterization of their structures is presented. The monomers were subjected to cationic polymerization using BF3·O(C2H5)2 as an initiator. The synthesized low-molar-mass compounds and oligomers were examined by differential scanning calorimetry, UV spectrometry, electron photoemission and time of flight techniques. The electron photoemission spectra of the films of synthesized materials revealed the ionization potentials of 5.12-5.34 eV. Hole drift mobilities of low-molar-mass compounds molecularly dispersed in bisphenol Z polycarbonate range from 2.6 × 10-8 to 1.7 × 10-6 cm2/V s at high electric fields as it was established by xerographic time of flight technique.
Synthesis of Novel Derivatives of Carbazole-Thiophene, Their Electronic Properties, and Computational Studies
Damit,Nordin,Ariffin,Sulaiman
, (2016)
A series of carbazole-thiophene dimers, P1-P9, were synthesized using Suzuki-Miyaura and Ullmann coupling reactions. In P1-P9, carbazole-thiophenes were linked at the N-9 position for different core groups via biphenyl, dimethylbiphenyl, and phenyl. Electronic properties were evaluated by UV-Vis, cyclic voltammogram, and theoretical calculations. Particularly, the effects of conjugation connectivity on photophysical and electrochemical properties, as well as the correlation between carbazole-thiophene and the core, were studied. Carbazole connecting with thiophenes at the 3,6-positions and the phenyl group as a core group leads to increased stabilization of HOMO and LUMO energy levels where the bandgap (Δ E) is significantly reduced.
A useful procedure for diiodination of carbazoles and subsequent efficient transformation to novel 3,6-bis(triethoxysilyl)carbazoles giving mesoporous materials
Maegawa, Yoshifumi,Goto, Yasutomo,Inagaki, Shinji,Shimada, Toyoshi
, p. 6957 - 6960 (2006)
Bis(pyridine)iodonium tetrafluoroborate (IPy2BF4) was successfully used as a diiodination reagent for carbazole and its derivatives to give 3,6-diiodocarbazoles in excellent yield. Subsequent rhodium-catalyzed disilylation of 3,6-diiodocarbazoles with triethoxysilane gave the corresponding 3,6-bis(triethoxysilyl)carbazoles, which are precursors for sol-gel polymerization, in good yield.
Synthesis and isolation of iodocarbazoles. Direct iodination of carbazoles by N-iodosuccinimide and N-iodosuccinimide-silica gel system
Bonesi,Erra-Balsells
, p. 77 - 87 (2001)
Carbazole (1) undergoes electrophilic aromatic substitution with various iodinating reagents. Although, 3-iodocarbazole (1b) and 3,6-diiodocarbazole (1d) obtained by iodination of carbazole were isolated and characterized sometime ago, 1-iodocarbazole (1a
Synthesis, photophysical, electrochemical and electrochemiluminescence properties of A2B2 zinc porphyrins: The effect of π-extended conjugation
Galván-Miranda, Elizabeth K.,Castro-Cruz, Hiram M.,Arturo Arias-Orea,Iurlo, Matteo,Valenti, Giovanni,Marcaccio, Massimo,Macías-Ruvalcaba, Norma A.
, p. 15025 - 15038 (2016)
The synthesis of two A2B2 porphyrins, {5,15-bis-[4-(octyloxy)phenyl]-porphyrinato}zinc(ii) (4) and {5,15-bis-(carbazol-3-yl-ethynyl)-10,20-bis-[4-(octyloxy)phenyl]-porphinato}-zinc(ii) (9), is reported. Their photophysical properties were studied by steady-state absorption and emission. Substituting the carbazolylethynyl moieties at two of the meso positions results in a large bathochromic shift of all the absorption bands, a notable increase in the absorption coefficient of the Q(0,0) band, and higher fluorescence quantum yield compared to porphyrin 4, with two unsubstituted meso positions. Cyclic voltammetry and digital simulation show that electrogenerated radical ions of 9 are more stable than those of 4. The lack of substituents at the meso positions of 4 leads to dimerization reactions of the radical cation. Despite this, the annihilation reaction of 4 and 9 produces very similar electrogenerated chemiluminescence (ECL) intensity. Spectroelectrochemical experiments demonstrate that the electroreduction of 9 leads to a strong absorption band that might quench the ECL.
A study of the properties, reactivity and anticancer activity of novel N-methylated-3-thiazolyl or 3-thienyl carbazoles and their Pd(II) and Pt(II) complexes
Reig, Marta,Bosque, Ramón,Font-Bardía, Mercè,Calvis, Carme,Messeguer, Ramon,Baldomà, Laura,Badía, Josefa,Velasco, Dolores,López, Concepción
, p. 134 - 145 (2018)
The synthesis and characterization of two hybrid N-methylated carbazole derivatives containing a thiazolyl or a thienyl ring is reported. The thiazolyl derivative has been also characterised by X-ray diffraction analysis. The study of its reactivity in front of [MCl2(dmso)2] (M = Pd or Pt) or Na2[PdCl4] in methanol has allowed us to isolate and characterize its complexes. However, for the thienyl analogue, the formation of any Pd(II) or Pt(II) complex was not detected, indicating that it is less prone to bind to the M(II) ions than its thiazolyl analogue. Density Functional Theory (DFT) and Time-Dependent Density Functional Theory (TD-DFT) calculations have also been carried out in order to rationalize the influence of the nature of the thiazolyl or thienyl group on the electronic delocalization. Molecular mechanics calculations show that the free rotation of the thiazolyl in relation to the carbazole requires a greater energy income than for its thienyl analogue. Studies of the cytotoxic activity of the new compounds on colon (HCT116) and breast (MDA-MB231 and MCF7) cancer cell lines show that the thiazolyl carbazole ligand and its Pt(II) complex are the most active agents of the series and in the MCF7 line their potency is higher than that of cisplatin. In the non-tumoral human skin fibroblast BJ cell line, all the compounds were less toxic than cisplatin. Their potential ability to modify the electrophoretic mobility of pBluescript SK+ plasmid DNA and to act as inhibitors of Topoisomerases I and IIα or cathepsin B has also been investigated.
Synthesis and properties of bipolar derivatives of 1,3,5-triazine and carbazole
Matulaitis,Kostiv,Grazulevicius,Peciulyte,Simokaitiene,Jankauskas,Luszczynska,Ulanski
, p. 45 - 58 (2016)
Three new bipolar star-shaped derivatives of 2,4,6-triphenyl-1,3,5-triazine containing carbazolyl groups were designed, synthesized and characterized. All the materials possess high thermal stability and high glass transition temperatures ranging 97-226 °C. Photophysical study of the dilute solutions and neat films of the synthesized compounds was performed. Lippert-Mataga plots revealed linear dependence of Stokes shifts on the orientation polarizability for all the compounds. The dilute solutions of the triazine derivatives exhibited high photoluminescence quantum yields reaching 0.85, while for the neat films photoluminescence efficiency of 0.20-0.33 was observed. Ionization potentials of the solid layers of carbazole-triazine adducts estimated by photoelectron spectroscopy were found to be in the range of 5.49-5.97 eV. Hole drift mobility of the materials well exceeded the magnitude of 10-3 cm2 V-1 s-1 at an electric field of 6.4 · 105 V/cm. The selected compounds were tested as light emitting materials in organic light emitting diodes based on host-guest systems.
A one-pot direct iodination of the Fischer-Borsche ring using molecular iodine and its utility in the synthesis of 6-oxygenated carbazole alkaloids
Naykode, Mahavir S.,Humne, Vivek T.,Lokhande, Pradeep D.
, p. 2392 - 2396 (2015)
An efficient regioselective iodination of the Fischer-Borsche ring has been achieved using molecular iodine, in a one-pot synthesis. The acid-, metal-, and oxidant-free conditions of the present method are highly convenient and practical. Furthermore, the one-pot direct iodination process is extended to the concise synthesis of glycozoline, 3-formyl-6-methoxy-carbazole, and 6-methoxy-carbazole-3-methylcarboxylate natural alkaloids. This method has been proven to be tolerant to a broad range of functional groups, with good to excellent yields.
Synthesis and properties of photocross-linkable carbazole dimers
Simkus,Tomkeviciene,Volyniuk,Kostjuk,Grazulevicius
, p. 47 - 54 (2017)
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.
