110677-45-7Relevant articles and documents
Direct Olefination of Fluorinated Quinoxalines via Cross- Dehydrogenative Coupling Reactions: A New Near-Infrared Probe for Mitochondria
Zhang, Zeyuan,Zheng, Yiwen,Sun, Zuobang,Dai, Zhen,Tang, Ziqiang,Ma, Jiangshan,Ma, Chen
, p. 2259 - 2268 (2017)
A large library of 5,8-distyrylquinoxaline fluorophores was synthesized in good-to-excellent yields via a palladium-catalyzed oxidative C–H/C–H cross-coupling of electron-deficient fluorinated quinoxalines with electron-rich styrenes. The resulting quinoxaline fluorophores (Qu-Fluors) exhibited tunable color emissions with the quantum yields of up to 83% and large Stokes shifts of up to 6236 cm?1 in dichloromethane. The bioimaging performance of the Qu-Fluors was shown to have potential as near-infrared fluorescent probes for mitochondria. (Figure presented.).
High-efficiency deep blue fluorescent emitters based on phenanthro[9,10-d]imidazole substituted carbazole and their applications in organic light emitting diodes
Gao, Zhao,Wang, Zhiming,Shan, Tong,Liu, Yulong,Shen, Fangzhong,Pan, Yuyu,Zhang, Huanhuan,He, Xin,Lu, Ping,Yang, Bing,Ma, Yuguang
, p. 2667 - 2676 (2014)
A series of highly efficient deep blue emitters comprising of carbazole and phenanthro[9,10-d]imidazole moieties are designed and synthesized. These compounds present deep blue emission, narrow FWHM, high quantum yields, high thermal and morphological stabilities. Among them, the design strategy of 2:1 ratio of phenanthro[9,10-d]imidazole and carbazole unit affords M2 with more balanced carrier injection and transporting properties. OLEDs using M2 as emitting layer is observed to deliver a truly deep blue CIE of y 3is attained with a maximum current efficiency of 33.35 cd A-1, a power efficiency of 22.99 lm W-1and a maximum external quantum efficiency of 9.47%. When doped with an orange fluorescent material, upon careful tuning the doping proportion, the two-emitting-component white OLED is successfully fabricated with a maximum current efficiency of 5.53 cd A-1and CIE coordinates of (0.313, 0.305). Both the non-doped and doped devices exhibited high operational stability with negligible efficiency roll-off over the broad current density range.
Development of a carbazole-based fluorescence probe for G-quadruplex DNA: The importance of side-group effect on binding specificity
Wang, Ming-Qi,Ren, Gui-Ying,Zhao, Shuang,Lian, Guang-Chang,Chen, Ting-Ting,Ci, Yang,Li, Hong-Yao
, p. 441 - 447 (2018)
G-quadruplex DNAs are highly prevalent in the human genome and involved in many important biological processes. However, many aspects of their biological mechanism and significance still need to be elucidated. Therefore, the development of fluorescent probes for G-quadruplex detection is important for the basic research. We report here on the development of small molecular dyes designed on the basis of carbazole scaffold by introducing styrene-like substituents at its 9-position, for the purpose of G-quadruplex recognition. Results revealed that the side group on the carbazole scaffold was very important for their ability to selectively recognize G-quadruplex DNA structures. 1a with the pyridine side group displayed excellent fluorescence signal turn-on property for the specific discrimination of G-quadruplex DNAs against other nucleic acids. The characteristics of 1a were further investigated with UV–vis spectrophotometry, fluorescence, circular dichroism, FID assay and molecular docking to validate the selectivity, sensitivity and detailed binding mode toward G-quadruplex DNAs.
Luminescence switching of a persistent room-temperature phosphorescent pure organic molecule in response to external stimuli
Xue, Pengchong,Sun, Jiabao,Chen, Peng,Wang, Panpan,Yao, Boqi,Gong, Peng,Zhang, Zhenqi,Lu, Ran
, p. 10381 - 10384 (2015)
4-(Carbazol-9-yl)benzaldehyde could emit yellow RTP, which could last for 3 s because of efficient intersystem crossing. Moreover, multicolor luminescent switches could be realized by simply applying a mechanical force stimulus.
Carbazole-containing push-pull chromophore with viscosity and polarity sensitive emissions: Synthesis and photophysical properties
Telore, Rahul D.,Sekar, Nagaiyan
, p. 1 - 8 (2016)
Carbazole based D-π-A extended styryl dyes with intramolecular charge transfer characteristics were synthesized. The intramolecular charge transfers of these D-π-A extended styryls have been examined with the study of photophysical properties like absorption, emission and quantum yield in various solvents of different polarities. All the dyes demonstrated positive solvatochromism. They showed largely improved photophysical properties and large Stokes shifts due to twist geometry. Oscillator strengths and transition state dipole moments have been studied to understand charge transfer within the molecules. The fluorescence molecular rotors properties of the series of extended styryls have been evaluated. The dyes having good charge transfer characteristics showed better FMR properties. Sensitivity of the fluorescence emission towards solvent polarity and viscosity has been investigated using fluorescence emission spectra.
Nonvolatile bistable resistive switching in a new polyimide bearing 9-phenyl-9H-carbazole pendant
Hu, Benlin,Zhuge, Fei,Zhu, Xiaojian,Peng, Shanshan,Chen, Xinxin,Pan, Liang,Yan, Qing,Li, Run-Wei
, p. 520 - 526 (2012)
A new polyimide bearing the functional pendant 9-phenyl-9H-carbazole moieties, poly[2,2-(4,4′-di(N-benzyloxycarbazole)-3,3′-biphenylene) propane-hexafluoroisopropylidenediphthalimide] (6F-BAHP-PC PI), has been designed as a functional material for resista
Self-Stabilized Amorphous Organic Materials with Room-Temperature Phosphorescence
Xu, Wei,Yu, Yaguo,Ji, Xiaonan,Zhao, Huarui,Chen, Jinming,Fu, Yanyan,Cao, Huimin,He, Qingguo,Cheng, Jiangong
, p. 16018 - 16022 (2019)
The stability of pure organic room-temperature phosphorescent (RTP) materials in air has been a research hotspot in recent years. Without crystallization or encapsulation, a new strategy was proposed to obtain self-stabilized organic RTP materials, based
Synthesis of Linear and V-Shaped Carbazolyl-Substituted Pyridine-3,5-dicarbonitriles Exhibiting Efficient Bipolar Charge Transport and E-Type Fluorescence
Vigante, Brigita,Leitonas, Karolis,Volyniuk, Dmytro,Andruleviciene, Viktorija,Simokaitiene, Jurate,Ivanova, Anna,Bucinskas, Audrius,Grazulevicius, Juozas V.,Arsenyan, Pavel
, p. 3325 - 3336 (2019)
With the aim of developing all-organic bipolar semiconductors with high charge mobility and efficient E-type fluorescence (so-called TADF) as environmentally friendly light-emitting materials for optoelectronic applications, four noble metals-free dyes with linear and V-shapes were designed using accepting pyridine-3,5-dicarbonitrile and donating carbazole units. By exploiting a donor-acceptor design strategy and using moieties with different donating and accepting abilities, TADF emitters with a wide variety of molecular weights were synthesized to achieve the optimum combination of charge-transporting and fluorescent properties in one TADF molecule. Depending on molecule structures, different TADF emitters capable of emitting in the range from 453 to 550 nm with photoluminescence quantum yields up to 98 % for the solutions in oxygen-free toluene were obtained. All compounds showed bipolar charge-transport. Hole mobility of 2.8×10?3 cm2/Vs at 7×105 V cm?1 was observed for the compound containing two di-tert-butyl-substituted carbazole moieties. The compounds were tested in both non-doped and doped organic light-emitting diodes using different hosts. It was shown that the developed TADF emitters are suitable for different color devices with electroluminescence ranging from blue to yellow and with brightness, maximum current and external quantum efficiencies exceeding 10 000 cd m?2, 15 cd/A, and 7 %, respectively.
Multifunctional phosphorescent iridium (III) complexes based on 2-phenylbenzothiazole derivative for highly efficient organic light-emitting diodes
Li, Xiao,Zang, Tie-Nan,Chi, Hai-Jun,Dong, Yan,Xiao, Guo-Yong,Zhang, Dong-Yu
, p. 51 - 57 (2014)
Phosphorescent robust heteroleptic iridium (III) [Ir(III)] complexes based on 2-(4-(9H-carbazol-9-yl)phenyl)benzothiazole integrated with three auxiliary ligand were designed, synthesized and used to fabricate organic light-emitting diodes (OLEDs). The Ir(III) complexes emitted intense phosphorescence with yellow or orange color at room temperature with high quantum efficiencies and relatively short lifetimes. The auxiliary ligand greatly influenced the electronic and photophysical properties of their corresponding heteroleptic Ir(III) complexes. The complexes showed reversible redox characteristics. Hole-only single-carrier devices indicated that three complexes all possessed excellent hole-transporting ability. The phosphorescent OLEDs using three Ir(III) complexes as dopants exhibited turn-on voltages of ca. 4 V, maximum current efficiencies of 22.3-44.2 cd A-1 and maximum power efficiencies of 18.3-23.3 lm W-1, which were superior to the (bt)2Ir(acac)-based device (19.1 cd A-1, 9.3 lm W -1) under the same condition. The elevated devices' performances based on the new Ir(III) complexes as emitters were probably attributed to the hole-transporting rigid carbazole moiety resulting in more balanced electron and hole transportation and recombination in emissive layer.
Photoinduced energy transfer in carbazole-BODIPY dyads
Reddy, Govind,Duvva, Naresh,Seetharaman, Sairaman,D'Souza, Francis,Giribabu, Lingamallu
, p. 27418 - 27428 (2018)
A series of carbazole (CBZ)-boron dipyrromethene (BODIPY) based donor-acceptor dyads, CB1, CB2, and CB3, with CBZ as an energy donor, tethered together with spacers of varied sizes i.e., phenyl bridge, biphenyl bridge and diphenylethyne bridge, respectively, are reported. The newly synthesized dyads were characterized by various spectroscopic techniques. A comparison of the absorption and electrochemical data of the dyads with their reference compounds (i.e., 9-phenyl-9H-carbazole (C0) and N,N′-difluoroboryl-1,3,7,9-tetramethyl-5-phenyldipyrrin (B0)) revealed minimal ground-state interactions between the chromophores. Selective excitation of CBZ in the dyads at 290 nm resulted in the quenching of the CBZ emission followed by the appearance of BODIPY emission, revealing efficient energy transfer from singlet excited CBZ (1CBZ?) to BODIPY. The photoinduced energy transfer phenomenon was studied in three different solvents of varying polarity. The driving forces for energy transfer (ΔGEN) for all the dyads were found to be exothermic. The rate constants for energy transfer, kENT, measured by the femtosecond transient absorption technique in toluene were found to be in the range of 0.8-2.0 × 1010 s-1, depending on the type of spacer between the CBZ and BODIPY entities, and were in close agreement with the theoretically estimated rates according to the F?rster energy transfer model. In contrast, selective excitation of BODIPY in these dyads at 485 nm resulted in small quenching of the BODIPY emission, suggesting a lack of major photochemical events originating from 1BODIPY?.
Synthesis and the effect of a peripheral N-arylcarbazole moiety on the acid-base and DNA binding properties of a novel RuII complex
Lue, Yuan-Yuan,Gao, Li-Hua,Han, Mei-Jiao,Wang, Ke-Zhi
, p. 430 - 436 (2006)
A novel RuII complex of [Ru(bpy)2(cpipH)](ClO 4)2 (where bpy = 2,2′-bipyridine, cpipH = 2-[4-(9H-carbazol-9-yl)phenyl]-1H-imidazol[4,5-f][1,10]phenanthroline) was synthesized. The binding of the complex to calf thymus DNA was investigated with UV/Vis absorption and luminescence titrations, steady-state emission quenching by [Fe(CN)6]4-, DNA competitive binding with ethidium bromide, and thermal denaturation. The pH effects on the UV/Vis absorption and emission spectra of the complex were also studied, and the ground- and excited-state ionization constants were derived. The results indicated that the complex intercalatively bound to the DNA, with an intrinsic binding constant of (8.2 ± 0.8) × 105 M-1 in buffered 50 mM NaCl, is stronger than the parent complex, [Ru(bpy)2(pip)]2+ (pip = 2-phenylimidazo[4,5-f][1,10]phenanthroline), and its excited states are 0.7-0.8 pKa units more basic than those of the ground states. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Two stimulus-responsive carbazole-substituted D–π–A pyrone compounds exhibiting mechanochromism and solvatochromism
Liu, Dongqi,Cao, Yuqi,Yan, Xilong,Wang, Bowei
, p. 2429 - 2439 (2019)
Two D–A compounds were designed and synthesized from 2,6-dimethyl-4-pyrone and carbazole compounds. Both of them exhibited unique fluorescence properties in the aggregated state. Red shifts of the spectrum of 102?nm and 130?nm were observed for BCSP and C
Synthesis, photophysical and electrochemical properties of novel D-π-D and D-π-a triphenylamino-chalcones and β-arylchalcones
Da Costa, Rafaela G.M.,Farias, Francisco R.L.,Maqueira, Luis,Neto, Carlos Castanho,Carneiro, Leonardo S.A.,Almeida, Joseany M.S.,Buarque, Camilla D.,Aucélio, Ricardo Q.,Limberger, Jones
, p. 81 - 89 (2019)
A series of triphenylamino (TPA)-chalcones and triphenylamino-β-arylchalcones, displaying either D-π-D or D-π-A architecture, were synthesized through aldol condensations and Heck reactions. The chalcone derivatives display intense absorption bands rangin
Synthesis and characterisation of RuII polypyridyl complexes: DNA-binding, photocleavage, and topoisomerase i and II inhibitory activity
He, Xiaojun,Yang, Guang,Sun, Xiaonan,Xie, Lingjun,Tan, Lifeng
, p. 1406 - 1414 (2013)
Two mixed-ligand ruthenium(ii) complexes [Ru(phen)2(cptcp)]2+ (Ru1; phen≤1,10-phenanthroline, cptcp≤2-(4-carbazol-9-yl-phenyl)-1H-1,3,7,8- tetraaza-cyclopenta-[l]-phenanthrene) and [Ru(phen)2(btcpc)]2+ (Ru2; btcpc≤9-butyl-6-(1H-1,3,7,8-tetraaza-cyclo-cyclopenta-[l]-phenanthren-2-yl) -9H-carbazole-3-carbaldehyde) have been synthesised and characterised. The DNA-binding behaviours of the two complexes have been investigated by using spectroscopic and viscosity measurements. Results suggest that the two complexes bind to DNA by intercalation. The photocleavage of plasmid pBR322 DNA indicates that Ru1 exhibits more effective DNA cleavage activity in comparison to that exhibited by Ru2 under the same conditions, and different cleavage mechanisms are determined. Topoisomerase inhibition and DNA strand passage assay confirm that Ru1 may act as an efficient dual inhibitor of topoisomerases I and II, whereas Ru2 may only act as a single inhibitor of topoisomerases II. CSIRO 2013.
Carbazole/triphenylamine-cyanobenzimidazole hybrid bipolar host materials for green phosphorescent organic light-emitting diodes
Patil, Bhausaheb,Lade, Jatin,Chiou, Shian-Sung,Cheng, Yen-Chia,Jadhav, Yogesh,Chetti, Prabhakar,Chang, Chih-Hao,Chaskar, Atul
, (2021)
With a view to attain balanced charge flux for higher device performance of PhOLEDs, we have used carbazole/triphenyl amine as hole transporting moiety and cyano along with benzimidazole as electron transporting core in 3-Cbz-ImdCN, 4-Cbz-ImdCN and TPA-Im
Multi-response quinoxaline-based fluorophores: Solvatochromism, mechanochromism, and water sensoring
Yu, Jia,Liu, Zhifang,Wang, Bowei,Cao, Yuqi,Liu, Dongqi,Wang, Yixian,Yan, Xilong
, p. 64 - 67 (2020)
Three new D-π-A type quinoxaline-cored fluorophores were elaborately designed and synthesized. It was found that P-1, P-2, and P-3 (Ps) all presented bathochromic-shifted mechanochromic (MFC) nature upon grinding, accompanied with 30 nm, 8 nm, and 37 nm r
Sensitive and selective Cu2+ sensor based on 4-(3-(thiophen-2-yl)-9H-carbazol-9-yl)benzaldehyde (TPCBZ) conjugated copper-complex
Rahman, Mohammed M.,Alamry, Khalid A.,Saleh, Tamer S.,Asiri, Abdullah M.
, p. 43 - 49 (2016)
4-(3-(thiophen-2-yl)-9H-carbazol-9-yl)benzaldehyde (TPCBZ) was synthesized under microwave irradiation with auto generated pressure (at 130.0 °C) and characterized by 1H NMR, 13C NMR, Mass and FTIR spectroscopy, thin-layer chromatogr
Photophysical and Electrochemical Properties of Highly π-Conjugated Bipolar Carbazole-1,3,4-Oxadiazole-based D-π-A Type of Efficient Deep Blue Fluorescent Dye
Najare, Mahesh Sadashivappa,Patil, Mallikarjun Kalagouda,Tilakraj, Tarimakki Shankar,Yaseen, Mohammed,Nadaf, AfraQuasar A,Mantur, Shivaraj,Inamdar, Sanjeev Ramchandra,Khazi, Imtiyaz Ahmed M
, p. 1645 - 1664 (2021)
In this contribution, we have designed and synthesized a novel carbazole-1,3,4-oxadiazole based bipolar fluorophore (E)-2-(4-(4-(9H-carbazol-9-yl)styryl)phenyl)-5-(4-(tertbutyl) phenyl)-1,3,4-oxadiazole (CBZ-OXA-IV). Wittig reaction is utilised for the synthesis of the designed bipolar target compound CBZ-OXA-IV.1H NMR, 13C NMR, FT-IR and ESI–MS results confirmed the designed chemical structure of the fluorophore CBZ-OXA-IV. The photophysical properties have been investigated in detail using UV–Vis absorption, photoluminescence spectroscopy. Also, the photoluminescence studies on solid state samples (as thin films) were carried out. The CBZ-OXA-IV dye emits intense deep blue fluorescence with observed absorption and emission maxima occurring are at 353?nm and 470?nm, respectively. Fluorophore CBZ-OXA-IV has shown high Stokes shift of 7052?cm?1. The experimentally measured optical band gap (Egopt) value is found to be 3.01?eV and the fluorescence quantum yields (Φf) is 0.40. The intramolecular charge transfer property of CBZ-OXA-IV dye was examined by using photophysical properties such as absorption, emission in different solvents of different varying polarities. In addition, Density Functional Theory computations are studied in detail including the MEP surface plots and natural bond orbital analysis. The electrochemical properties have been investigated in detail by using cyclic voltammetry measurements. Thermal gravimetric analysis (TGA) and differential scanning calorimetry (DSC) measurement results display a high thermal stability with decomposition temperature (Td5%) 387?°C and a large glass transition temperature (Tg) of 98?°C. The obtained results demonstrated that the novel bipolar fluorophore CBZ-OXA-IV could play an important role in organic optoelectronics and possibly can be utilized as bipolar transport materials for electroluminescence applications in optoelectronic devices/OLEDs. Graphical abstract: [Figure not available: see fulltext.]
