37500-95-1Relevant articles and documents
Preorganized anion traps for exploiting anion-π interactions: An experimental and computational study
Bretschneider, Anne,Andrada, Diego M.,Dechert, Sebastian,Meyer, Steffen,Mata, Ricardo A.,Meyer, Franc
, p. 16988 - 17000 (2013)
1,3-Bis(pentafluorophenyl-imino)isoindoline (AF) and 3,6-di-tert-butyl-1,8-bis(pentafluorophenyl)-9H-carbazole (BF) have been designed as preorganized anion receptors that exploit anion-π interactions, and their ability to bind chlor
Carbazole based polymers as hosts for blue iridium emitters: Synthesis, photophysics and high efficiency PLEDs
Stanislovaityte, Egle,Simokaitiene, Jurate,Raisys, Steponas,Al-Attar, Hameed,Grazulevicius, Juozas V.,Monkman, Andrew P.,Jankus, Vygintas
, p. 8209 - 8221 (2013)
This article reports the synthesis of new carbazole based polymers and their application as hosts in sky-blue polymer light emitting devices (PLEDs) with a solution-processed emitting layer doped with a cyclometalated Ir(iii) complex. We systematically investigate their effect on the PLED performance. A current efficiency of 19.7 cd A-1 and a brightness of 1850 cd m -2 were achieved with these polymers. The roll-off in electrophosphorescent quantum efficiency in PLEDs was shown to arise mainly from triplet-triplet annihilation between dopants in the hosts with tert-butyl groups. It has been shown that in the devices with hosts without tert-butyl groups the efficiency roll-off is additionally affected by electric field quenching. In these carbazole based polymers, triplet dimers are formed and tert-butyl groups do not limit the intermolecular interactions to prevent triplet dimer formation, nevertheless tert-butyl groups reduce charge transport.
Methoxy- and tert-butyl-substituted meta-bis(N-carbazolyl)phenylenes as hosts for organic light-emitting diodes
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.
, p. 317 - 326 (2019)
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.
Thermally activated delayed fluorescence enantiomers for solution-processed circularly polarized electroluminescence
Sun, Sibing,Wang, Jun,Chen, Lingfeng,Chen, Runfeng,Jin, Jibiao,Chen, Cailin,Chen, Shufen,Xie, Guohua,Zheng, Chao,Huang, Wei
, p. 14511 - 14516 (2019)
Circularly polarized organic light-emitting diodes (CP-OLEDs) with thermally activated delayed fluorescence (TADF) characteristics are receiving increasing interest, as they have shown improving efficiencies of circularly polarized electroluminescence (CPEL). Here, we developed a series of TADF enantiomers based on chiral binaphthalene, an acceptor (A) of cyanopyridine, and donors (D) of carbazoles in a chiral-A-D architecture. Good solubility, high luminescence yields, and excellent chiral stability with a photoluminescence dissymmetry factor (gPL) up to 5.8 × 10-4 were achieved. Efficient CP-OLEDs using these chiral TADF molecules as dopants were successfully fabricated, exhibiting high external quantum efficiencies (EQEs) up to 12.4% and opposite CPEL signals with gEL of 6 × 10-4/-8.6 × 10-4 in vacuum-deposited devices. More impressively, the solution-processed TADF CP-OLEDs result in much larger gEL values (3.5 × 10-3/-3.9 × 10-3) with EQEs up to 10.6%. This discovery is encouraging and instructive, which could stimulate the development of high-performance CP-OLEDs using chiral TADF molecules through solution-processing approaches.
Solution-processible carbazole dendrimers as host materials for highly efficient phosphorescent organic light-emitting diodes
Li, Jiuyan,Zhang, Ting,Liang, Yunjing,Yang, Ruixia
, p. 619 - 628 (2013)
A group of dendrimers with oligo-carbazole dendrons appended at 4,4′- positions of biphenyl core are synthesized for use as host materials for solution-processible phosphorescent organic light-emitting diodes (PHOLEDs). In comparison with the traditional
Studies on the Enantioselective Iminium Ion Trapping of Radicals Triggered by an Electron-Relay Mechanism
Bahamonde, Ana,Murphy, John J.,Savarese, Marika,Brémond, éric,Cavalli, Andrea,Melchiorre, Paolo
, p. 4559 - 4567 (2017)
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.
Design, synthesis and application of carbazole macrocycles in anion sensors
Bobacka, Johan,Darnell, Astrid,Haav, Kristjan,Haljasorg, T?iv,Ilisson, Mihkel,Kadam, Sandip A.,Leito, Ivo,Rüütel, Alo,Saar, Indrek,Toom, Lauri,Yrj?n?, Ville
, p. 1901 - 1914 (2020)
Carboxylate sensing solid-contact ion-selective electrodes (ISEs) were created to provide a proof-of-concept ISE development process covering all aspects from in silico ionophore design to functional sensor characterization. The biscarbazolylurea moiety was used to synthesize methylene-bridged macrocycles of different ring size aiming to fine tune selectivity towards different carboxylates. Cyclization was achieved with two separate strategies, using either amide synthesis to access up to –[CH2]10–macrocycles or acyl halides to access up to –[CH2]14–macrocycles. Seventy-five receptor–anion complexes were modelled and studied with COSMO-RS, in addition to all free host molecules. In order to predict initial selectivity towards carboxylates, 1H NMR relative titrations were used to quantify binding in DMSO-d6/H2O solvent systems of two proportions – 99.5%:0.5% m/m and 90.0%:10.0% m/m, suggesting initial selectivity towards acetate. Three ionophores were selected for successful sensor prototype development and characterization. The constructed ion-selective electrodes showed higher selectivity towards benzoate than acetate, i.e., the selectivity patterns of the final sensors deviated from that predicted by the classic titration experiments. While the binding constants obtained by NMR titration in DMSO-d6/H2O solvent systems provided important guidance for sensor development, the results obtained in this work emphasize the importance of evaluating the binding behavior of receptors in real sensor membranes.
Water oxidation catalyzed by a charge-neutral mononuclear ruthenium(III) complex
Lu, Zhongkai,Gao, Yan,Chen, Hu,Liu, Zhao,Sun, Licheng
, p. 1304 - 1310 (2017)
A new charge-neutral Ru(iii) complex RuL(pic)3 (1) (H3L = 3,6-di-tert-butyl-9H-carbazole-1,8-dicarboxylic acid, pic = 4-picoline) was synthesized and fully characterized. This complex promoted chemical and photochemical water oxidation efficiently with turnover frequencies of 0.28 s-1 and 5 min-1, respectively. In particular, for photochemical water oxidation, complex 1 showed excellent stability and good activity. The X-ray crystal structure, electrochemical results, and the detection of the RuIV-OH intermediate by high-resolution mass spectrometry revealed that complex 1 exchanged its 4-picoline ligand with water at the RuIII state to form the authentic water oxidation catalyst. The kinetics studies suggested a reaction mechanism involving nucleophilic attack by a water molecule.
Optimised synthesis of monoanionic bis(NHC)-pincer ligand precursors and their Li-complexes
Jürgens, Eva,Buys, Kai N.,Schmidt, Anna-Theresa,Furfari, Samantha K.,Cole, Marcus L.,Moser, Michael,Rominger, Frank,Kunz, Doris
, p. 9160 - 9169 (2016)
Herein we report the optimised synthesis of a versatile bis(imidazole)carbazole framework 4, a precursor to our previously reported C-N-C bis(NHC) pincer ligand, bimca. We have also used 4 as a basis for constructing a library of fully characterised bis(i
Synthesis and photophysical properties of carbazole-based blue light-emitting dendrimers
Adhikari, Ravi M.,Mondal, Rajib,Shah, Bipin K.,Neckers, Douglas C.
, p. 4727 - 4732 (2007)
(Graph Presented) A new class of highly fluorescent and stable carbazole-based dendrimers (1-5) that contain the ethynylbenzene and diethynylbenzene cores has been synthesized and characterized. They show very high extinction coefficients of absorption (Amax ≈ 328-353 nm) and high quantum yields of fluorescence (λmax ≈ 386-437 nm; ΦF ≈ 0.72-0.89; τF ≈ 2.09-3.91 ns) in dichloromethane. The quantum yields of fluorescence of 1-5 in the solid state are equally high (λmax ≈ 385-422 nm; ΦF ≈ 0.40-0.85). These data indicate their potential use as blue-emitting materials in organic light-emitting diodes (OLEDs).
Carbazole dendronised triphenylamines as solution processed high T g amorphous hole-transporting materials for organic electroluminescent devices
Moonsin, Preecha,Prachumrak, Narid,Rattanawan, Ratanawalee,Keawin, Tinnagon,Jungsuttiwong, Siriporn,Sudyoadsuk, Taweesak,Promarak, Vinich
, p. 3382 - 3384 (2012)
Carbazole dendrimers up to 4th generation were synthesized. They showed significantly high Tg, amorphous and stable electrochemical properties, and great potential as solution processed hole-transporting materials for OLEDs. Alq3-based green de
Solvatochromic properties of 3,6-di-tert-butyl-8H-indolo[3,2,1-de]acridin- 8-one
Czerwinska, Marlena,Wierzbicka, Malgorzata,Guzow, Katarzyna,Bylinska, Irena,Wiczk, Wieslaw
, p. 19310 - 19320 (2014)
The spectral and photophysical properties of newly synthesized 3,6-di-tert-butyl-8H-indolo[3,2,1-de]acridin-8-one were studied. To determine the contribution of specific and nonspecific interactions of this compound with solvents, the solvatochromic metho
Polymerizations for olefin-based polymers
-
Page/Page column 48-49, (2022/02/16)
The invention provides a process to form an olefin-based polymer, said process comprising polymerizing at least one olefin in the presence of at least one catalyst system comprising the reaction product of the following: A) at least one cocatalyst; and B) a procatalyst comprising a metal-ligand complex of Formula (I), as described herein:
Carbazole-modified thiazolo[3,2-: C] [1,3,5,2]oxadiazaborinines exhibiting aggregation-induced emission and mechanofluorochromism
Potopnyk, Mykhaylo A.,Kravets, Mykola,Luboradzki, Roman,Volyniuk, Dmytro,Sashuk, Volodymyr,Grazulevicius, Juozas Vidas
supporting information, p. 406 - 415 (2021/01/29)
Two highly emissive carbazole-containing thiazole-fused oxadiazaborinines were designed and synthesized. These N,O-chelated organoboron dyes displayed large Stokes shifts and remarkable solvatofluorochromism in solutions, as well as good thermal stability
