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.
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.
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
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.
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.
Triazine-based aromatic amines as new glass-forming charge transport materials
Vaitkeviciene,Grazulevicius,Peciuraite,Grigalevicius,Jankauskas
, p. 141 - 150 (2007)
Various diarylamino-substituted 1,3,5-triazine derivatives have been synthesized by Cu catalyzed Ullmann-type arylamino-aryl coupling reaction. Full characterization of the compounds structures by mass spectrometry, IR and electronic absorption, as well as 1H NMR spectroscopy is presented. Some of the compounds represent amorphous materials with glass transition temperatures exceeding 84C and with thermal decomposition starting at temperatures330C. The electron photoemission spectra of the materials were recorded and the ionisation potentials of ca. 5.3-5.8eV were established. Time-of-flight hole drift mobility of some diarylamino-substituted triazines molecularly dispersed in bisphenol Z polycarbonate approached 10-5cm2/Vs at high electric field.
Enantioselective recognition of tartaric acids with ethynylated carbazole-based chiral bisboronic acid chemosensors with improved response at acidic pH
Liu, Yifan,Zhang, Xin,Guo, Huimin,Wu, Yubo,Li, Qiuting,Liu, Liping,Zhao, Jianzhang
, p. 1979 - 1986 (2011)
Chiral bisboronic acid chemosensors based on ethynylated carbazole were prepared. The chiral chemosensors show red-shifted emission than the chemosensors with unsubstituted carbazole fluorophore. a-PET effect was found for the chemosensors, which is different from our previous observation of the d-PET effect for boronic acid chemosensors based on carbazole. Enantioselective recognition of tartaric acids was implicated with these chemosensors. Consecutive fluorescence emission enhancement/diminishment were observed with increasing the concentration of the tartaric acids, which is tentatively assigned to the transition of the binding stoichiometry from 1:1 binding to 1:2 binding. In particularly interesting is the improved fluorescence response at acidic pH for recognition of tartaric acids, which is rarely observed for a-PET chemosensors. We propose that the sensing is due to hybrid mechanism of a-PET/d-PET and conformational restriction upon binding. Our results will be useful for design of chiral boronic acid chemosensors with improved fluorescence response at acidic pH, which are rarely reported.
Solution-processable naphthalene and phenyl substituted carbazole core based hole transporting materials for efficient organic light-emitting diodes
Kumar, Sudhir,An, Chih-Chia,Sahoo, Snehasis,Griniene, Raimonda,Volyniuk, Dmytro,Grazulevicius, Juozas V.,Grigalevicius, Saulius,Jou, Jwo-Huei
, p. 9854 - 9864 (2017)
Solution-processable molecular hole transporting materials (HTMs) are extremely crucial in order to realize low cost, high throughput, and roll-to-roll fabrication of large area organic light emitting diodes for display and lighting applications. In this report, a series of naphthalene and phenyl substituted carbazole core based HTMs, 3-(1-naphthyl)-9-(2-phenylvinyl)carbazole (NPVCz), 3,6-di-(1-naphthyl)-9-phenylvinylcarbazole (DNPVCz), and 3,6-diphenyl-9-(2-phenylvinyl)carbazole (DPPVCz) are successfully synthesized and characterized. The synthesized HTMs possess excellent solubility in common organic solvents. By using a fluorescent tris(8-hydroxyquinolinato)aluminium emitter, we demonstrate an enhancement of 135%, from 1.7 to 4.5 cd A-1, in the current efficiency of an organic light emitting diode (OLED) by replacing the conventional HTM, N,N′-di(1-naphthyl)-N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine (NPB), with the NPVCz counterpart. Moreover, the current efficiency of a conventional tris[2-phenylpyridinato-C2,N]iridium(iii) based phosphorescent green OLED device increases from 46.4 to 66.2 cd A-1 by substituting the NPB with NPVCz. These findings suggest that this type of solution-processable molecular HTM will be a promising contender for high efficiency OLED devices.
Easy accessible blue luminescent carbazole-based materials for organic light-emitting diodes
Reig, Marta,Gozálvez, Cristian,Bujaldón, Roger,Bagdziunas, Gintautas,Ivaniuk, Khrystyna,Kostiv, Nataliya,Volyniuk, Dmytro,Grazulevicius, Juozas V.,Velasco, Dolores
, p. 24 - 35 (2017)
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.
Dynamic Generation of G-Quadruplex DNA Ligands by Target-Guided Combinatorial Chemistry on a Magnetic Nanoplatform
Jana, Snehasish,Panda, Deepanjan,Saha, Puja,Pantos, G. Dan,Dash, Jyotirmayee
, p. 762 - 773 (2019)
Dynamic combinatorial chemistry (DCC) has emerged as a promising strategy for template-driven selection of high-affinity ligands for biological targets from equilibrating combinatorial libraries. However, only a few examples using disulfide-exchange-based DCC are reported for nucleic acid targets. Herein, we have demonstrated that gold-coated magnetic nanoparticle-conjugated DNA targets can be used as templates for dynamic selection of ligands from an imine-based combinatorial library. The implementation of DCC using DNA nanotemplates enables efficient identification of the lead compounds, from the dynamic combinatorial library via magnetic decantation. It further allows quick separation of DNA nanotemplates for reuse in DCC reactions. The identified lead compound exhibits significant quadruplex versus duplex DNA selectivity and suppresses promoter activity of c-MYC gene that contains G-quadruplex DNA forming sequence in the upstream promoter region. Further cellular experiments indicated that the lead compound is able to permeate into cell nuclei and trigger a DNA damage response in cancer cells.
Synthesis and Properties of Blue Fluorescent Dyes Based on Diphenylamine by Introducing an Acetylene Linkage Group with Carbazole and 1,8-Naphthalimide
Kim, Tae-Heon,Kwon, Su-Hyeon,Choi, Jae-Hong
, p. 1229 - 1232 (2019)
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Carbazole modified oligonucleotides: Synthesis, hybridization studies and fluorescence properties
Gouda, Alaa S.,J?rgensen, Per T.,Przypis, ?ukasz,Walczak, Krzysztof,Wengel, Jesper
, p. 6935 - 6948 (2020/10/02)
Synthesis of the novel thiophenyl carbazole phosphoramidite DNA building block 5 was accomplished in four steps using a Suzuki-Miyaura cross-coupling reaction from the core carbazole and it was seamlessly accommodated into a 9-mer DNA-based oligonucleotide by incorporation at the flanking 5′-end in combination with a central insertion of an LNA-T nucleotide. The carbazole-containing oligonucleotide was combined in different duplex hybrids, which were characterized by thermal denaturation, circular dichroism and fluorescence studies. The carbazole monomer modulates the duplex stability in various ways. Thus, monomer Z increased the thermal stability of the 9-mer towards the complementary 9-mer/15-mer DNA duplex by 4.2 °C. Furthermore, indications of its intercalation into the duplex were obtained by modeling studies and robust decreases in fluorescence emission intensities upon duplex formation. In contrast, no clear intercalating tendency was corroborated for monomer Z within the DNA/RNA hybrid duplex as indicated by moderate quenching of the fluorescence and similar duplex thermal stabilities relative to the corresponding control duplex. The recognition efficiencies of the carbazole modified oligonucleotide toward single nucleotide mismatches were studied with two 15-mer model targets (DNA and RNA). For both systems, mismatches positioned at the juxtaposition of the carbazole monomer showed pronounced deceases in thermal denaturation temperature. Steady-state fluorescence emission studies of all mismatched duplexes with incorporation of Z monomer typically displayed efficient fluorescence quenching.
Long-Lived Triplet Excited State Accessed with Spin–Orbit Charge Transfer Intersystem Crossing in Red Light-Absorbing Phenoxazine-Styryl BODIPY Electron Donor/Acceptor Dyads
Dick, Bernhard,Dong, Yu,Elmali, Ayhan,Karatay, Ahmet,Zhao, Jianzhang
, (2020/06/08)
Orthogonal phenoxazine-styryl BODIPY compact electron donor/acceptor dyads were prepared as heavy atom-free triplet photosensitizers (PSs) with strong red light absorption (?=1.33×105 M?1 cm?1 at 630 nm), whereas the previously reported triplet photosensitizers based on the spin-orbit charge transfer intersystem crossing (SOCT-ISC) mechanism show absorption in a shorter wavelength range (T=333 μs) was observed for the new dyads. In comparison, the triplet state lifetime of the same chromophore accessed with the conventional heavy atom effect (HAE) is much shorter (τT=1.8 μs). Long triplet state lifetime is beneficial to enhance electron or energy transfer, the primary photophysical processes in the application of triplet PSs. Our approach is based on SOCT-ISC, without invoking of the HAE, which may shorten the triplet state lifetime. We used bisstyrylBodipy both as the electron acceptor and the visible light-harvesting chromophore, which shows red-light absorption. Femtosecond transient absorption spectra indicated the charge separation (109 ps) and SOCT-ISC (charge recombination, CR; 2.3 ns) for BDP-1. ISC efficiency of BDP-1 was determined as ΦT=25 % (in toluene). The dyad BDP-3 was used as triplet PS for triplet-triplet annihilation upconversion (upconversion quantum yield ΦUC=1.5 %; anti-Stokes shift is 5900 cm?1).
