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.).
Enhancing the coplanarity of the donor moiety in a donor-acceptor molecule to improve the efficiency of switching phenomenon for flash memory devices
Ren, Wusheng,Zhuang, Hao,Bao, Qing,Miao, Shifeng,Li, Hua,Lu, Jianmei,Wang, Lihua
, p. 127 - 134 (2014)
Two conjugated small molecules were synthesized by Heck coupling reaction, wherein 1,8-naphthalimide acted as an electron acceptor, while either carbazole or triphenylamine, which contributed the different coplanarity, acted as electron donors, respectively. The devices based on both materials show non-volatile flash memory characteristics, and the effect of molecular coplanarity of the donor groups on the device performance was precisely studied. The results indicated that the reproducibility of the switching phenomenon for the memory device based on the carbazole containing naphthalimide derivative was much better than that based on the triphenylamino based naphthalimide due to the rigid carbazole moiety which improved the surface morphology as revealed by atomic force microscopy measurement. Therefore, the significance of the coplanarity of the donor moiety on improving reproducibility of switching phenomenon for memory device applications was revealed.
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.
Exploration of high-performance light-conversion agents based on cyanostilbene and phenanthrenecarbonitrile backbones:E/Zand position isomerism, high-contrast Michael addition reaction activity and intramolecular photocyclization
Wang, Yongtao,Qian, Zhean,Li, Xueming,Qin, Anjun,Guo, Yanjun,Tang, Benzhong
, p. 12681 - 12693 (2021)
As light-conversion agents, traditional organic fluorescent dyes easily suffer from solid-state fluorescence quenching and photooxidation, leading to the deterioration of their application performance. To enhance the fluorescence emission and photostability of light-conversion agents in a doped film, in this paper, some luminogens with a cyanostilbene or a phenanthrenecarbonitrile backbone were designed and synthesized based on aggregation-induced emission (AIE) theory,E/Zisomerization and our previous research results, and were characterizedviaNMR, HR-MS and single-crystal X-ray diffraction. The experimental results indicate that bothZ-oCaandZ-pCaexhibit high-contrast Michael addition reaction activity and intramolecular photocyclization, as well as fluorescence quantum yields in the doped film, but similarE/Zphotoisomerization and AIE activity. Besides,E-oCashows stable configuration in solution, but not forZ-pCa, meanwhile,E-oCaandZ-oCadisplay different AIE activities. More importantly,C-Cawith a twisted molecular configuration succeeded in avoiding fluorescence quenching induced by intramolecular photocyclization, emitting strong fluorescence in the solid state and the PABT-doped film (PLQY = 0.65). After an intensified UV radiation of 20 h, 94% of the initial intensity is reserved, and emission peaks exhibit tiny shifts. Based on matching excitation and emission maxima (374 nm and 433 nm), high PLQY, excellent photostability and light-conversion quality in the doped film,C-Cais a potential high-performance light-conversion agent. Finally, light-conversion properties and the intrinsic mechanism are discussed in detail using the UV-vis absorption spectra, fluorescence emission spectra, crystal analysis, the photosynthetic photon flux density, the percentages of different wavelength bands, theoretical calculations and XRD patterns. This work is the first report on a highly efficient light-conversion agent with the phenanthrenecarbonitrile backbone; meanwhile, it contributes considerably to the molecular design of photostable luminogens and basic photochemistry.
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.
meso-borneol- andmeso-carbazole-substituted porphyrins: multifunctional chromophores with tunable electronic structures and antitumor activities
Fu, Bo,Dong, Xinyi,Yu, Xiaoxiao,Zhang, Zhen,Sun, Lei,Zhu, Weihua,Liang, Xu,Xu, Haijun
, p. 2141 - 2146 (2021)
Herein, a series of fiveC2symmetric H2porphyrins withmeso-borneol andmeso-carbazole units have been synthesized and isolated. An analysis of the electronic structures was carried out by spectroscopic investigations and electrochemica
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.
Synthesis, crystal structure and photoluminescence of phosphorescent copper (I) complexes containing hole-transporting carbazoly moiety
Yu, Tianzhi,Chai, Haifang,Zhao, Yuling,Zhang, Chengcheng,Liu, Peng,Fan, Duowang
, p. 179 - 185 (2013)
Two new mononuclear Cu(I) complexes based on 2-(2′-pyridyl) benzimidazolyl derivative ligand containing hole-transporting carbazole (L), [Cu(L)(DPEphos)](BF4) and [Cu(L)(PPh3)2] (BF4), where L = (4-(9H-carbazol-
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.
Carbazole-based sensitizers for potential application to dye sensitized solar cells
Duvva, Naresh,Kanaparthi, Ravi Kumar,Kandhadi, Jaipal,Marotta, Gabriele,Salvatori, Paolo,De Angelis, Filippo,Giribabu, Lingamallu
, p. 383 - 394 (2015)
Two push-pull molecules employing carbazole and alkyl thiophene (CAR-THIOHX) or carbazole and triphenylamine (CAR-TPA) as donor moieties, with the cyanoacrylic group as the acceptor, have been designed and synthesized by simple organic transformations. Photophysical and electrochemical studies revealed the potential of these two systems in dye sensitized solar cells (DSSC). Under standard irradiation conditions, CAR-TPA and CAR-THIOHX exhibited 2.12 and 1.83% of overall power conversion efficiencies respectively. The moderate photovoltaic efficiency of the sensitizers has been attributed to the poor light absorption of the sensitizers in the visible region. Density functional theory (DFT) calculations have shown a strong intramolecular charge transfer character, with the HOMOs of both the sensitizers exclusively localized on the corresponding donor moieties and LUMOs on the cyanoacrylic acid acceptor. On the other hand, the calculated high dihedral angle between the carbazole donor and the phenyl bridge for these sensitizers impedes the conjugation along the dyes backbone, and thus leads to less extended and intense absorption spectra in the visible region. [Figure not available: see fulltext.]
