- Tuning the optoelectronic properties of phenothiazine-based D?A-type emitters through changing acceptor pattern
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Two novel blue emitters, 10-ethyl-3-(1,4,5-triphenyl-1H-imidazol-2-yl)-phenothiazine (PTHBI) and 10-ethyl-3-(1-phenyl-1H-phenanthro[9,10-d]imidazole-2-yl)-phenothiazine (PTHPI), employing a donor (10-ethyl-phenothiazine) and an acceptor (1,4,5-triphenyl-1
- Qiu, Xu,Shi, Jinjin,Xu, Xin,Lu, Yuansheng,Sun, Qikun,Xue, Shanfeng,Yang, Wenjun
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- Substituent effect on photophysical properties, crystal structures and mechanochromism of D-π-A phenothiazine derivatives
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This study aimed to investigate the effect of substituents on the photophysical properties of four 10-ethyl-3-styryl-phenothiazine derivatives with CH3O (PVBMA), COOMe (PVBM), CHO (PVBA), or NO2 (NSP) moieties in solution and in crys
- Zhang, Tong,Han, Yanning,Liang, Meng,Bian, Weixiao,Zhang, Yan,Li, Xiaoting,Zhang, Chunyu,Xue, Pengchong
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- Phenothiazine and diphenylsulfone-based donor–acceptor π-systems exhibiting remarkable mechanofluorochromism
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Two donor–acceptor luminophores PTZ-DPS and BPTZ-DPS, which are constructed by electron-donor phenothiazine and electron-acceptor diphenylsulfone moiety, are designed and synthesized. Through the effective combination of phenothiazine and diphenylsulfone unit, PTZ-DPS and BPTZ-DPS molecules adopt twisted molecular conformation, unique intramolecular charge transfer (ICT) behavior and intense fluorescence in both solution and solid state. The solid-state luminescence efficiencies of the two luminophores reach 32.84% and 39.69%, respectively. It is particularly noteworthy that both PTZ-DPS and BPTZ-DPS exhibit switchable mechanofluorochromism with high contrast. Upon external force stimulation, the fluorescence colors of the PTZ-DPS and BPTZ-DPS solid powders that change dramatically from initial bright green and yellow to orange, respectively, are observed. Meanwhile, the emission bands red shift from 499 nm to 564 nm–589 nm and 592 nm, respectively, suggesting the large spectral red shifts of 90 nm and 28 nm. Moreover, the mechanofluorochromic (MFC) behavior of PTZ-DPS and BPTZ-DPS also show good reversibility when fume the ground powders by DCM vapor. PXRD and spectral data suggest that the phase transition between crystalline to amorphous states is responsible for MFC behavior of PTZ-DPS and BPTZ-DPS, and the red-shift in the PL spectrum upon grinding originates from the planarization of the molecular conformation and subsequent planar intramolecular charge transfer (PICT).
- Feng, Xiucun,Fu, Shengjie,Huang, Qian,Liu, Xingliang,Xu, Defang,Zhang, Weidong,Zhang, Zhan,Zhou, Hongke
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- Significant improvement of dye-sensitized solar cell performance using simple phenothiazine-based dyes
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A series of simple phenothiazine-based dyes have been synthesized, in which a cyanoacrylate acceptor directly attached to the C(3) position of phenothiazine, and an additional linear electron-rich (4-hexyloxy)phenyl group at C(7) on the opposite side of t
- Hua, Yong,Chang, Shuai,Huang, Dandan,Zhou, Xuan,Zhu, Xunjin,Zhao, Jianzhang,Chen, Tao,Wong, Wai-Yeung,Wong, Wai-Kwok
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- Phenothiazine-based organic dyes with two anchoring groups on TiO 2 for highly efficient visible light-induced water splitting
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New phenothiazine-based organic dyes with two anchoring groups at 3,7 positions and systematic alkyl chains on nitrogen were prepared. Their TiO 2-Pt composites showed excellent photo-catalytic activities in visible light-induced water splitting. Interestingly, phenothiazine dyes with longer alkyl chains showed better stability in catalytic systems.
- Lee, Jeho,Kwak, Jiwon,Ko, Kyoung Chul,Park, Ji Hoon,Ko, Ju Hong,Park, Nojin,Kim, Eunchul,Ryu, Do Hyun,Ahn, Tae Kyu,Lee, Jin Yong,Son, Seung Uk
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- Lipase-catalyzed kinetic resolutions of racemic 1-(10-ethyl-10H- phenothiazin-1,2, and 4-yl)ethanols and their acetates
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The synthesis of both enantiomers of 1-(10-ethyl-10H-phenothiazin-1,2, and 4-yl)ethanols 1a-c and their acetates via enantioselective methanolysis of the corresponding racemic esters rac 2a-c with lipase B from Candida antarctica (CaL-B) or/and by acylation of the racemic alcohols with the lipase A or lipase B from C. antarctica (CaL-A and CaL-B) is described. The absolute configuration of enantiopure 1-(10-ethyl-10H-phenothiazin-1-yl)ethyl acetate 2a was assigned as (R) by using QM/MM(hf/3-21g:uff) calculations within the CaL-B (1LBT crystal structure) enzymic environment.
- Brem, Juergen,Pilbak, Sarolta,Paizs, Csaba,Banoczi, Gergely,Irimie, Florin-Dan,Tosa, Monica-Ioana,Poppe, Laszlo
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- Observation of peroxynitrite overproduction in cells during 5-fluorouracil treatment: Via a ratiometric fluorescent probe
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We describe a colorimetric and fluorescent probe 3a to detect cellular peroxynitrite with high selectivity and sensitivity. 3a was successfully applied in the bioimaging of exogenous and endogenous peroxynitrite in living cells. The up-regulation of peroxynitrite in cancer cells and normal cells during 5-fluorouracil treatment was finally monitored.
- Cao, Xinhua,Cui, Beibei,Hou, Ji-Ting,Wang, Bingya,Wang, Shan,Ye, Yong,Zhang, Man,Zhang, Yongru
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- Impact of hydroxy and octyloxy substituents of phenothiazine based dyes on the photovoltaic performance
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Two novel organic dyes containing hydroxy and octyloxy substituents onto a phenothiazine skeleton were synthesized and their effects on the photovoltaic performance were studied. Hydroxy acts as an ancillary anchoring unit along with the carboxylic group, while the phenothiazine modified moiety acts as an electron donor. The photophysical and electrochemical studies revealed that maximum absorbance of the dye with the hydroxy group in the solution was blue shifted and its band gap increased, indicating that donor acceptor strength was reduced as compared to the octyloxy substituted dye. Furthermore, electron lifetime of the organic dye with the hydroxy moiety was shorter due to smaller resistance of electron recombination. Contrarily the dye with octyloxy moiety exhibited higher electron lifetime and open-circuit photovoltage leading to an overall power conversion efficiency of 6.32% under standard AM 1.5G illumination. The IPCE was over 80% in the region between 450 and 500 nm.
- Iqbal, Zafar,Wu, Wu-Qiang,Zhang, Hai,Hua, Peng-Li,Fang, Xiaoming,Kuang, Dai-Bin,Wang, Lingyun,Meier, Herbert,Cao, Derong
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- Two novel fluorescent probes based on phenothiazine: synthesis and “naked-eye” colorimetric recognition of Hg2+
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Two novel colorimetric and fluorescent probes 2-(1,3-dithiolanes)-10-ethyl phenothiazine (PHE–Ed) and 2-(1,3-dithianes)-10-ethyl phenothiazine (PHE–Pd) based on phenothiazine were successfully synthesized, and their structure was confirmed by NMR and high resolution mass spectra. Fluorescence investigations revealed that the synthesized probes could be used for the selective detection of Hg2+, which was accompanied with an obvious color change from colorless to light yellow. The applicable ability of the two probes was investigated by a series of competitive experiments, solid colorimetric experiments, and applied?experiments, which proved that these probes showed high sensitivity and great potential to detect Hg2+ in environmental analysis systems. Furthermore, the detection mechanism of the probes was investigated by FT-IR spectra and NMR spectra, and the results indicated that the detection of Hg2+ was accomplished through the Hg2+-promoted deprotection of thioacetal.
- Wang, Chuane,Wang, Lizhen,Fang, Shimin,Qin, Dawei,Zhou, Jianhua,Yang, Geng,Jin, Shuangshuang,Duan, Hongdong
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- Electric and steric hindrance effects of substituents on luminescence and force-stimuli response of cyanovinyl phenothiazine derivatives
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Six cyanovinyl phenothiazine derivatives bearing substituents with different sizes, and electron-donating and -withdrawing abilities were designed and synthesized. The effect of substituents on photophysical properties in solution and solid states were sy
- Zhang, Tong,Han, Yanning,Chen, Qiao,Chen, Xinyu,Xue, Pengchong
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- Novel cyanoacetamide integrated phenothiazines: Synthesis, characterization, computational studies and in vitro antioxidant and anticancer evaluations
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A series of novel phenothiazine based cyanoacrylamides 6a-d have been synthesized from phenothiazine through multistep synthetic strategy. The structure of these novel molecules (6a-d) has been determined by FT-IR, 1H NMR and 13C NMR spectral techniques. Computational studies were carried out for the synthesized compounds 6a-d using DFT method with B3LYP/6-311G(d,p) basis set. The target compounds 6a-d have been screened for their in vitro antioxidant and anticancer activity. The antioxidant data revealed that the compounds 6c and 6d exhibited high radical scavenging activity with IC50 value of 37.32 and 39.07 μM, respectively. Furthermore, all the synthesized compounds displayed significant in-vitro anticancer activity against both the pancreatic tumor cells AsPC1 and SW1990. Particularly, the compound 6c exhibited the highest activity among the molecules tested against both the tumor cells viz., AsPC1 and SW1990.
- Krishnan, Kannan Gokula,Kumar, Chandran Udhaya,Lim, Wei-Meng,Mai, Chun-Wai,Thanikachalam, Punniyakoti V.,Ramalingan, Chennan
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- Two novel blue phosphorescent host materials containing phenothiazine-5,5-dioxide structure derivatives
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Two novel D-A bipolar blue phosphorescent host materials based on phenothiazine-5,5-dioxide: 3-(9H-carbazol-9-yl)-10-ethyl- 10H-phenothiazine-5,5-dioxide (CEPDO) and 10-butyl-3-(9H-carbazol-9-yl)-10H-phenothiazine-5,5-dioxide (CBPDO) were synthesized and characterized. The photophysical, electrochemical and thermal properties were systematically investigated. CEPDO and CBPDO not only have a high triplet energy but also show a bipolar behavior. Moreover, their fluorescence emission peaks are in the blue fluorescence region at 408 nm and the fluorescence quantum efficiency (φ) of CEPDO and CBPDO were 62.5% and 59.7%, respectively. Both CEPDO and CBPDO showed very high thermal stability with decomposition temperatures (Td) of 409 and 396 °C as well as suitable HOMO and LUMO energy levels. This preferable performance suggests that CEPDO and CBPDO are alternative bipolar host materials for the PhOLEDs.
- Xie, Feng-Ming,Ou, Qingdong,Zhang, Qiang,Zhang, Jiang-Kun,Dai, Guo-Liang,Zhao, Xin,Wei, Huai-Xin
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- Efficient red fluorescent OLEDs based on aggregation-induced emission combined with hybridized local and charge transfer state
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Limited by the energy gap law and large conjugate structures, red organic light-emitting diodes (OLEDs) have long been criticized for their efficiency problems. The aggregation-induced emission (AIE) effect and the reverse intersystem crossing process can lead to high photoluminescent quantum yields (PLQYs) and high exciton utilization efficiency (EUE), two key objectives for obtaining efficient OLEDs. In this work, we chose benzothiadiazole as the acceptor (A) and triphenylamine and phenothiazine as the donors (Ds) to design and synthesize a D–A–D red fluorescent molecule, PBTPA. Results of systematic photophysical measurements indicated PBTPA to exhibit AIE trending, manifesting as aggregation-induced enhanced emission and the characteristics of hybridized local and charge transfer (HLCT) states. These features facilitated high solid-state luminescence efficiency and high exciton utilization to be achieved. A non-doped device fabricated using PBTPA displayed a red electroluminescence peak at 656 nm, corresponding to the Commission International de L'Eclairage coordinates of (0.65, 0.32), and an external quantum efficiency of 1.62percent. By calculation, the EUE reached a value of 50percent. According to the results of theoretical calculations, the effective hot exciton channel between the second triplet (T2) and the lowest singlet (S1) was responsible for the high EUE. This EUE value is relatively good for this type of red OLEDs. Evidence indicates that combining AIE and HLCT has excellent potential to aid the discovery of new-generation highly efficient red OLEDs.
- Cang, Miao,Cui, Wei,Sun, Mizhen,Wang, Runze,Xu, Lei,Xue, Shanfeng,Yang, Wenjun,Yu, Yuan,Zhou, Huayi
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- A mitochondria-targeted fluorescent probe for fast detecting hypochlorite in living cells
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A fast-responsive fluorescent probe PI-Py was designed and synthesized for sensitive and selective detecting hypochlorite (ClO?). The probe PI-Py was intrinsically non-fluorescent due to the PET effect of the phenothiazine moiety. After reacting with ClO?, the PET effect was blocked, and a strong green emission of the BODIPY unit was recovered. The probe PI-Py showed an excellent selectivity towards ClO? in comparison of other ROS. The limit of detection for ClO? was calculated to be 1.7 nM, proving the probe's high sensitivity. Moreover, the probe PI-Py has been proved to be effective in visualizing the variations of exogenous ClO? in living HeLa cells. A co-localization study employing Mito Tracker red reveals that the PI-Py is specifically located in the mitochondria.
- Li, Hongfang,Miao, Yu,Liu, Zhixue,Wu, Xue,Piao, Chunxiang,Zhou, Xin
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- Phenacyl Phenothiazinium Salt as a New Broad-Wavelength-Absorbing Photoinitiator for Cationic and Free Radical Polymerizations
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A novel broad-wavelength-absorbing photoinitiator based on phenacyl phenothiazinium hexafluroantimonate (P-PTh) possessing both phenacyl and phenothiazine chromophoric groups was reported. P-PTh absorbs light at UV, Visible and Near-IR region. Photophysical, photochemical, and computational investigations revealed that P-PTh in solution decomposes at all wavelengths by homolytic and heterolytic cleavages and generates cationic and radical species, which could efficiently initiate cationic and free radical polymerizations. It is anticipated that the photoinitiator with such wavelength flexibility may open up new pathways in curing applications of formulations of pigment systems.
- Liu, Ren,Xu, Dandan,Yagci, Yusuf,Zhang, Yuchao,Zhou, Yufan,Zhu, Yi
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- Synthesis, optical characterization, and solvatochromism study of new two-photon absorption compounds
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The new donor-π-acceptor/acceptor-π-acceptor compounds (FQQ, KZQ, JYQ, and LVQ) were facilely synthesized and characterized by infrared, proton nuclear magnetic resonance, mass spectrometry, and elemental analysis. Their UV-visible absorption, one-photon excited fluorescence, two-photon absorption, and two-photon excited fluorescence were systematically investigated in different solvents. The experiment results indicate that all these compounds exhibit relatively strong up-converted fluorescence and obvious solvatochromic effects. KZQ shows the largest σ value of 707 GM in THF upon 830 nm excitation. Its excellent optical properties provide a promising alternative as a polarity-sensitive two-photon fluorescent probe. Aided with the quantum chemical density functional theory calculations, the relationships between the structures and the properties were studied.
- Zhou, Yan-Tao,Cai, Zhi-Bin,Pan, Yu-Lu,Bai, Li,Zheng, Guo-Chuang,Li, Sheng-Li,Tian, Yu-Peng
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- Directly Attached Bisdonor-BF2 Chelated Azadipyrromethene-Fullerene Tetrads for Promoting Ground and Excited State Charge Transfer
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The efficiency and mechanism of electron- and energy-transfer events occurring in both natural and synthetic donor–acceptor systems depend on their distance, relative orientation, and the nature of the surrounding media. Fundamental knowledge gained from model studies is key to building efficient energy harvesting and optoelectronic devices. Faster charge separation and slower charge recombination in donor–acceptor systems is often sought out. In our continued effort to build donor–acceptor systems using near-IR sensitizers, in the present study, we report ground and excited-state charge transfer in newly synthesized, directly linked tetrads featuring bisdonor (donor=phenothiazine and ferrocene), BF2-chelated azadipyrromethane (azaBODIPY) and C60 entities. The tetrads synthesized using multi-step synthetic procedure revealed strong charge-transfer interactions in the ground state involving the donor and azaBODIPY entities. The near-IR emitting azaBODIPY acted as a photosensitizing electron acceptor along with fullerene whereas the phenothiazine and ferrocene entities acted as electron donors. The triads (bisdonor–azaBODIPY) and tetrads revealed ultrafast photoinduced charge separation leading to D.+–azaBODIPY.?–C60 and D.+–azaBODIPY–C60.? (D=phenothiazine or ferrocene) charge separated states from the femtosecond transient absorption spectral studies in both polar and nonpolar solvent media. The charge-separated states populated the triplet excited state of azaBODIPY prior returning to the ground state.
- Collini, Melissa A.,Thomas, Michael B.,Bandi, Venugopal,Karr, Paul A.,D'Souza, Francis
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- The azatryptophan-based fluorescent platform for in vitro rapid screening of inhibitors disrupting IKKβ-NEMO interaction
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The nuclear factor-κB (NF-κB) plays an important role in inflammatory and immune responses. Aberrant NF-κB signaling is implicated in multiple disorders, including cancer. Targeting the regulatory scaffold subunit IκB kinase γ (IKKγ/NEMO) as therapeutic interventions could be promising due to its specific involvement in canonical NF-κB activation without interfering with non-canonical signaling. In this study, the use of unnatural amino acid substituted IKKβ with unique photophysical activity to sense water environment changes upon interaction with NEMO provides a powerful in vitro screening platform that would greatly facilitate the identification of compounds having the potential to disrupt IKKβ-NEMO interaction, and thus specifically modulate the canonical NF-κB pathway. We then utilized a competitive binding platform to screen the binding ability of a number of potential molecules being synthesized. Our results suggest that a lead compound (?)-PDC-099 is a potent agent with ascertained potency to disrupt IKKβ-NEMO complex for modulating NF-κB canonical pathway.
- Chao, Wei-Chih,Chiang, Tzu-Hsuan,Chaudhari, Prakash D.,Lin, Li-Ju,Lu, Jyh-Feng,Hong, Bor-Cherng,Wang, Jinn-Shyan,Lin, Ta-Chun,Shen, Jiun-Yi,Chou, Pi-Tai
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- Two novel two-photon polymerization initiators with extensive application prospects
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Two novel two-photon polymerization initiators, 10-ethyl-3-E-(4-(N,N ′-di-n-butylamino)styryl)phenothiazine 5 and 10-ethyl-3,7-E,E-bis(4-(N,N′-di-n-butyl amino)styryl) phenothiazine 6, have been efficiently synthesized with room temp
- Tian, Yupeng,Zhang, Mingliang,Yu, Xiaoqiang,Xu, Guibao,Ren, Yan,Yang, Jiaxiang,Wu, Jieying,Zhang, Xuanjun,Tao, Xutang,Zhang, Shengyi,Jiang, Minhua
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- Synthesis and characterization of three organic dyes with various donors and rhodanine ring acceptor for use in dye-sensitized solar cells
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A series of new organic dyes comprising carbazole, iminodibenzyl, and phenothiazine moieties as the electron donors and rhodanine ring as the electron acceptor/anchoring groups were designed and developed for use in dye-sensitized solar cells. HOMO and LUMO energy level tuning was achieved by varying the carbazole, iminodibenzyls and phenothiazine donors. This was evidenced by spectral and electrochemical experiments and density functional theory calculations. Electrochemical studies indicated that the phenothiazine unit was much more effective in lowering the ionization potential than were the iminodibenzyl and carbazole units. The phenothiazine dye shows a solar-energy-to-electricity conversion efficiency (η) of 4.87%; the carbazole and iminodibenzyl dyes show η of 2.54% and 3.52%, respectively. These findings reveal that using carbazole, iminodibenzyl and phenothiazine donors as light-harvesting sensitizers are promising candidates for dye-sensitized solar cells.
- Wu,Tsao,Chen,Su,Chang,Wang,Lin,Sun
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- A new phenothiazine-based fluorescence sensor for imaging Hg2+ in living cells
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A new phenothiazine-based sensor PHE-Ad for monitoring Hg2+ has been designed and synthesized based on the intramolecular charge transfer (ICT) mechanism. The probes were characterized by FTIR, 1H NMR, and HRMS, and their optical properties were detected by UV and FL. It's showed the probes detection of Hg2+ compared to other metal ions (Mg2+, Cu2+, Hg2+, Ag+, Co2+, Cr3+, Al3+, Ni2+, Zn2+, Ca2+, Fe3+, Fe2+, K+, Na+, and Cd2+) based on the test results. Besides, the detection limits were determined to be 2.12 × 10?8 M through the standard curve plot. In addition, sensor PHE-Ad shows high selectivity and sensitivity for Hg2+ with a fast response in a suitable pH range. Furthermore, taking into account its good “turn-on” fluorescent sensing behavior and low cell cytotoxicity, PHE-Ad was successfully applied to detect and image Hg2+ in real water samples and living cells, which shows great potentials for application in environmental and biological systems.
- Sun, Yucheng,Wang, Lizhen,Zhou, Jianhua,Qin, Dawei,Duan, Hongdong
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- Synthesis and bioapplication of a highly selective and sensitive fluorescent probe for HOCl based on a phenothiazine-dicyanoisophorone conjugate with large Stokes shift
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Herein, a fluorescent probe, Dcp-EPtz, for HOCl based on a strong push-pull phenothiazine-dicyanoisophorone conjugate was prepared. The probe exhibits a very large Stokes shift of over 170 nm. Dcp-EPtz turns out to be a fast-responsive (10 s) fluorescent
- Zheng, Dasheng,Qiu, Xiaoying,Liu, Chang,Jiao, Xiaojie,He, Song,Zhao, Liancheng,Zeng, Xianshun
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- Phenothiazine-based benzoxazole derivates exhibiting mechanochromic luminescence: The effect of a bromine atom
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Two phenothiazine-based benzoxazole derivates (PVB and BPVB) were designed and synthesized, and their photophysical properties were studied and compared. The results showed that both compounds emitted strong fluorescence in solution and in the solid state. Their emission wavelengths were also strongly affected by solvent polarity, indicating intramolecular charge transfer (ICT) transitions. Interestingly, the two compounds exhibited different mechanochromism. The ground film of PVB without bromine atoms can self-cure and change into the original film within 15 min at room temperature. The fluorescence of the ground film for BPVB showed no changes for at least 2 weeks. Meanwhile, a higher contrast fluorescence change was observed for the solid film of BPVB with bromine atoms under grinding, although PVB and BPVB exhibited similar spectral red shifts after grinding. Based on the spectral results and single-crystal structures, a mechanochromic mechanism is given.
- Xue, Pengchong,Yao, Boqi,Sun, Jiabao,Xu, Qiuxia,Chen, Peng,Zhang, Zhenqi,Lu, Ran
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- Development of an ultrasensitive Ru(II) complex-based fluorescent probe with phenothiazine unit for selective detection HOCl and its application in water samples
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A near-infrared probe Ru-1 with a phenothiazine derivative moiety as a responsive unit was designed to sensitively and selectively recognize HOCl in pure PBS solution. Upon addition of HOCl to a PBS solution of Ru-1, S-atom of the phenothiazine unit oxidized to sulfoxide, accompanied with a marked fluorescence enhancement about 60 fold at 635 nm. Probe Ru-1 displayed excellent water-solubility (PBS solution), low detection limit (4.4 nM), long fluorescence lifetime (354.36 ns) and large Stokes shift (175 nm). The experiments of its quantitative detection HOCl in water samples implied the probe Ru-1 possessed potential application in the environment.
- Zhang, Jiulong,Zhang, Daobin,Xiao, Lin,Pu, Shouzhi
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- Effect of a bridge unit on the mechanochromism of phenothiazine-based Schiff bases
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Two phenothiazine derivatives bridged with Schiff base groups were prepared, and investigations were conducted to study their mechanofluorochromic (MFC) behavior. When a mechanical force was applied, the compound PPD (N,N′-bis(10-ethyl-phenothiazin-2-ylmethylene)-p-phenylenediamine) changed its color from yellow to orange, exhibiting a significant MFC behavior. The reversible MFC behavior of PPD could be accomplished via grinding and fuming with CHCl3. Spectral analysis indicated that PPD molecules were packed in an H-Aggregate form in the as-synthesized crystal, whilst it had transformed to an amorphous state under external grinding. The X-ray analysis revealed that the transition from the crystalline structure to the amorphous state would result in the color change. Moreover, PED (N,N′-bis(10-ethyl-phenothiazin-2-ylmethylene)-ethylenediamine) with two isolated chromophores did not exhibit an MFC behavior, while no phase transition from crystal to the amorphous solid was found under grinding.
- Yang, Zicheng,Xue, Pengchong,Zhang, Lulu,Chen, Peng
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- Preparation of 4-substituted 10-ethylphenothiazines
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Under appropriate reaction conditions 10-ethylphenothiazine 1 undergoes lithiation at C-4 using an excess of sec-butyllithium-N,N,N′,N′-tetramethylethane-1,2-diamine in diethyl ether. Reaction of the lithiated intermediate with a variety of carbon, halogen, sulfur and silicon electrophiles affords several new 4-substituted 10-ethylphenothiazines 3a-i in good yields.
- Ebdrup, Soren,Jensen, Marianne Schou,Vedso, Per
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- A novel highly sensitive and selective fluorescent sensor for imaging mercury(ii) in living cells
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A novel phenothiazine-based derivative was designed and synthesized in this work, this molecule exhibited an obvious fluorescence quenching upon addition of Hg2+ due to the formation of a 1:1 metal-ligand complex. In addition to the high sensitivity toward Hg(ii), it also displayed a high selectivity for Hg2+ over other transition metal ions in a rapid response time (2+ in biological systems. the Partner Organisations 2014.
- Zhou, Chen,Song, Yan,Li, Yapeng
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- Synthesis and evaluation of photophysical and electrochemical properties of vinyl chalcogenide derivatives of phenothiazines
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The Wittig-Horner mediated syntheses of phenothiazines carrying vinylsulfide and vinylselenide motifs attached to the aromatic ring(s) or connected to the central nitrogen atom of the heterocycle, and the subsequent study of their photophysical and electr
- Dilelio, Marina Cardoso,Kaufman, Teodoro S.,Iglesias, Bernardo Almeida,Silveira, Claudio C.
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- Design synthesis and property research based on phenothiazine reversible fluorescent probe
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The invention relates to the field of fluorescent probes, and provides a fluorescent probe capable of good selectivity GSH, in particular to a fluorescent probe which takes phenothiazine as a light emitting group and reacts with a Michael reaction acceptor - active double bond as a reaction site to synthesize a reversible specific identification GSH. The structural formula is as follows. The fluorescent probe of the present invention has high selectivity and sensitivity for GSH, a 1% DMSO (PBS) buffer solution containing pH=7.4, a probe (10 μm) pair Cys (200 μm). Hcy (15 μm) And GSH (5 mm) In response 35 min, the probe can have good selectivity for GSH through ultraviolet and fluorescence spectrometer detection results. In response to GSH different concentrations, as GSH concentration increases, the fluorescence emission intensity gradually decreases at 606 nm, fluorescence emission intensity and GSH concentration are in a linear relation in a certain range, and the fluorescence probe has the advantages of high GSH action speed, strong selectivity, high sensitivity, simple synthesis method, easily available raw materials and easiness in popularization.
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Paragraph 0018-0019
(2021/12/07)
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- Synthesis and Density Functional Theory Studies of Pyridinyl hydrazide-Tethered Fused Thiazine
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Synthesis of pyridinyl hydrazide-tethered fused thiazine 6 has been accomplished by adopting multistep synthetic strategy and its structure has been established based on analytical and spectroscopic techniques. Density functional theory (DFT) studies of the molecule 6 have been performed employing DFT-B3LYP method with 6-311++G(d,p) basis set. Vibrational analysis and ultraviolet-visible spectral analysis results obtained from DFT studies have been found to correlate well with the ones obtained experimentally. To determine the energetic behavior of the synthesized compound, Mulliken population analysis has been carried out. To anticipate the location of electrostatic potentials and related properties of the same, molecular electrostatic potential analysis has been made. Besides, to have an idea about the charge transfer interface within the molecule, highest occupied molecular orbital and lowest unoccupied molecular orbital analyses have been performed.
- Gokulakrishnan, Kannan,Padmavathy, Krishnaraj,Ramalingan, Chennan,Saravanan, Vadivel,Sugunadevi, Ayyanar
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p. 479 - 487
(2021/11/22)
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- Novel Phenothiazinyl Acrylonitrile Hybrids: Synthesis, Biological, and Density Functional Theory Studies
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A series of phenothiazinyl acrylonitrile hybrids 6a-6h has been synthesized through multi-step synthesis and elucidated the structures of the same based on spectral and physical methods. Density functional theory (DFT)-B3LYP theoretical studies of a typic
- Krishnan, Kannan Gokula,Kumar, Chandran Udhaya,Lim, Wei-Meng,Mai, Chun-Wai,Padmavathy, Krishnaraj,Ramalingan, Chennan,Saravanan, Vadivel
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p. 301 - 311
(2021/08/03)
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- Improved synthesis of: N -ethyl-3,7-bis(trifluoromethyl)phenothiazine
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N-Ethyl-3,7-bis(trifluoromethyl)phenothiazine is a highly soluble redox shuttle for overcharge protection in lithium-ion batteries with an oxidation potential of ca. 3.8 V vs. Li+/0 in carbonate solvents. This compound has enabled extensive overcharge protection of LiFePO4/graphite cells and does so at high charging rates at high concentrations. Our initial synthesis of this compound suffered from low yields and difficult purifications. Here we report a cleaner, higher-yielding synthesis and additional characterization of the product and its stable radical cation salt. This journal is
- Attanayake, N. Harsha,Casselman, Matthew D.,Ergun, Selin,Kaur, Aman Preet,Odom, Susan A.,Parkin, Sean R.
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supporting information
p. 11349 - 11355
(2020/07/15)
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- Phenothiazine dye for detecting hypochlorite ions as well as preparation method and application thereof
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The invention discloses a phenothiazine dye for detecting hypochlorite ions as well as a preparation method and application thereof. The preparation method comprises the following steps: dissolving phenothiazine and bromo-ethane in a solvent, adding sodium hydroxide, purifying to obtain 10-ethyl-10H-phenothiazine; dropwise adding phosphorus oxychloride into N,N-dimethyl formamide, carrying out reactions at a low-temperature, adding 10-ethyl-10H-phenothiazine, carrying out a reaction to obtain 10-ethyl-10H-phenothiazine-3-formaldehyde, dissolving 3-methylquinoline and methyl iodide into anhydrous toluene, adding acetone, carrying out purification to obtain 1,2-dimethylquinoline-1-iodide; dissolving 10-ethyl-10H-phenothiazine-3-formaldehyde and 1,2-dimethylquinoline-1-iodide, dropwise addingpiperidine, and purifying to obtain a target product. The fluorescent probe only has fluorescence response to hypochlorite, and has the characteristics of good water solubility, high selectivity, high response speed, low detection cost and high sensitivity.
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Paragraph 0039-0041; 0045-0047; 0051-0053
(2020/06/04)
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- Fluorescent probe for detecting hypochlorous acid/sodium hypochlorite as well as preparation method and application thereof
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The invention belongs to the technical field, and particularly relates to a fluorescent probe for detecting hypochlorous acid/sodium hypochlorite as well as a preparation method and application thereof. The preparation method comprises the following steps: reacting 10H-phenothiazine with bromoethane to obtain 10-ethyl-10H-phenothiazine; carrying out a Vilsmeier reaction on the 10-ethyl-10H-phenothiazine to obtain 3-formyl-10-ethyl-10H-phenothiazine; reacting 3-diethylamino phenol with the 3-formyl-10-ethyl-10H-phenothiazine to obtain 9-(10-ethyl-10H-phenothiazine)-3,6-bis(diethylamino) xanthylium chloride, namely the fluorescent probe for detecting hypochlorous acid/sodium hypochlorite disclosed by the invention. The fluorescent probe is used for detecting hypochlorous acid/sodium hypochlorite in living cells, the hypochlorous acid/sodium hypochlorite fluorescent probe is mixed with a phosphate buffer solution and a DMF buffer solution and then added into a to-be-detected solution to obtain a mixed solution, and whether hypochlorous acid/sodium hypochlorite exists or not is detected through the change of 596 nm fluorescence intensity.
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Paragraph 0034-0042
(2020/10/14)
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- Phenothiazine and amide-ornamented novel nitrogen heterocyclic hybrids: synthesis, biological and molecular docking studies
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The synthesis of novel hybrids, namely, phenothiazine and amide-ornamented nitrogen heterocycles (25-34) has been accomplished utilizing a multi-step synthetic protocol and the structures have been established based on physical and spectral techniques. Of these, the hybrids possessing meta-nitro (26), para-fluoro (28), meta- and para-methyl (31), ortho-bromo (33) and ortho- and para-dimethyl (34) phenyl carboxamide scaffolds exhibited superior anti-inflammatory profiles over the standard diclofenac sodium. A hybrid integrated with a para-fluorophenyl carboxamide moiety (28) showed the highest DPPH radical scavenging activity among the chemical entities synthesized. Furthermore, the results of anticancer evaluations implied that the hybrid tethered with a phenyl carboxamide structural unit (29) exerted superior activity when compared with other hybrids against the pancreatic cancer cells SW1990 and AsPC1. Molecular docking between the hybrid 29 and B-cell lymphoma 2 reflects its appreciable binding affinity (-8.84 kcal mol-1). The results revealed that these chemical entities can serve as potent biological agents and/or efficient intermediates for the construction of potent biological agents.
- Iniyaval, Shunmugam,Karuppasamy, Ayyanar,Lim, Wei-Meng,Mai, Chun-Wai,Padmavathy, Krishnaraj,Ramalingan, Chennan,Sivaramakarthikeyan, Ramar
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p. 4049 - 4060
(2020/03/19)
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- Synthesis, spectral characterization and antitumor activity of phenothiazine derivatives
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Different types of phenothiazine derivatives were synthesized by reactions of 10-alkyl-10H-phenothiazine-3-carbaldehydes. Structures of the prepared compounds were confirmed through spectroscopic techniques such as IR, 1H NMR, 13C NMR and mass spectroscopy. All the compounds were studied for their antitumor activities.
- Venkatesan, Kasi,Satyanarayana, Vardhineedi Sri Venkata,Sivakumar, Amaravadi,Ramamurthy, Chitteti,Thirunavukkarusu, Chinnasamy
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p. 2722 - 2728
(2020/04/16)
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- Method for catalyzing reduction of iminodibenzyl carbon-based derivative
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The invention relates to a method for catalyzing reduction of an iminodibenzyl carbon-based derivative. For the first time, non-transition metal compound sodium triethylborohydride is used as a catalyst, the reduction reaction of the iminodibenzyl carbon-based derivative with an inexpensive and easily available organoboron reagent can be catalyzed conveniently under mild conditions to prepare an iminodibenzyl product. Compared with a traditional method, the method generally has the advantages that the catalyst is cheap and easy to obtain, operation is convenient and reaction is safe. For the first time, the selective reduction reaction of the iminodibenzyl carbon-based derivative with the organoboron reagent is catalyzed by a non-transition metal catalyst, and a practical and novel reaction strategy is provided for the laboratory preparation or industrial production of the iminodibenzyl product.
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Paragraph 0009-0012
(2019/11/12)
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- Hg2+ fluorescent probe and preparation method thereof
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The invention belongs to the field of fluorescent probes, and specifically relates to a fluorescent probe capable of detecting Hg2+ and a preparation method thereof. The fluorescent probe promotes a deprotection reaction to generate a novel compound in the presence of mercury ions; ultraviolet absorption generates red shift, and fluorescence generates red shift; the fluorescent probe is significantly reinforced; meanwhile, the fluorescent probe has good selectivity and strong resistance to metal ion interference, is rapid in response, is a purposeful, simple, rapid and sensitive mercury-ion specific detection reagent, and can be applied to the field of materials or the field of sensors.
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Paragraph 0030; 0031; 0034; 0035; 0038; 0039; 0042; 0043
(2019/04/26)
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- Phenothiazine and amide-ornamented dihydropyridines: Via a molecular hybridization approach: Design, synthesis, biological evaluation and molecular docking studies
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A series of novel phenothiazinyldihydropyridine dicarboxamides 7a-7j was synthesized by adopting a multi-step synthetic strategy and characterized through physical and spectral techniques. Among them, the chemical entities with para-fluoro (7d), ortho-bromo and-fluoro (7f and 7i), ortho- A nd para-methyl (7e) and meta- A nd para-methoxy (7h) substituents exhibited either similar or superior anti-inflammatory activities with respect to the standard drug diclofenac sodium. Besides, the chemical entities with ortho-bromo and-fluoro substituents as well as meta-nitro substituents (7f, 7g and 7i) showed enhanced radical scavenging activities when compared to standard ascorbic acid. Furthermore, anticancer studies revealed that the meta- A nd para-chloro-substituted molecule 7a exerted the best activity against all the pancreatic cancer cells tested. Also, appreciable binding affinity (-8.10 kcal mol-1) was observed during molecular docking between B-cell lymphoma 2 and 7a. The structural diversifications of the potent chemical entities besides further exploration in connection with the biological profiles of the same are underway.
- Sivaramakarthikeyan, Ramar,Iniyaval, Shunmugam,Padmavathy, Krishnaraj,Liew, Hui-Shan,Looi, Chin-King,Mai, Chun-Wai,Ramalingan, Chennan
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p. 17046 - 17057
(2019/11/14)
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- Piece of Hg cloth2+ Fluorescent probe and preparation method thereof (by machine translation)
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The detection mechanism of the fluorescence probe disclosed by the invention, can be used as a solid-state colorimetric reagent to conveniently and accurately and. efficiently detect mercury ions in the solution, and the fluorescence, probe can be applied to the field of materials or, sensors, pH. (by machine translation)
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Paragraph 0030-0031; 0034-0035; 0038-0039; 0042-0043; 0046
(2020/01/12)
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- Carbazole-phenothiazine organic dye and application of same to dye-sensitized solar cells
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The invention relates to a carbazole-phenothiazine organic dye and application of the same to dye-sensitized solar cells. The pure organic dye has phenothiazine and carbazole groups which are connected through para-position or ortho-position benzene, and the general formula of the organic dye is shown in a figure as described in the specification. When the dye disclosed by the invention is appliedto a dye-sensitized solar device, high photoelectric conversion efficiency is obtained. The preparation method of the dye is relatively simple in process and low in cost; and a cell prepared from thedye is high in photoelectric conversion efficiency and has commercial application prospects.
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Paragraph 0058; 0062; 0063
(2019/12/25)
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- A far-red-emissive AIE active fluorescent probe with large stokes shift for detection of inflammatory bowel disease: In vivo
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Inflammatory bowel disease (IBD) is a group of chronic remittent or progressive inflammatory gastrointestinal tract diseases, accompanying impaired barrier function. Effective real-time monitoring of the IBD progression in time is critical to the success of bowel therapy and the improvement of patient outcomes. However, there is relatively little information regarding the detection of the intestinal barrier. In this study, we have judiciously designed and synthesized a novel D-π-A based far-red-emissive AIE active fluorescent Probe (PTZB-FR). PTZB-FR exhibits properties suitable for in vivo imaging, such as FR emission, good photostability, large Stokes shift (~184 nm), and low cytotoxicity. Moreover, confocal fluorescence microscopy and flow cytometry assay reveal the effective internalization of PTZB-FR. Most importantly, imaging living mice after oral administration of PTZB-FR confirms that fluorescence in the intestinal lumen diminishes in Dextran sulfate sodium (DSS)-induced colitis, which is attributed to disruption of intestinal barrier integrity caused by a DSS-induced colitis model, highlighting PTZB-FR as a promising reagent in the detection of intestinal barrier function during clinical examination.
- Xu, Wanfu,He, Liying,Xia, Qi,Jia, Chunhong,Geng, Lanlan,Yang, Min,Xu, Zhaohui,Chen, Peiyu,Cheng, Yang,Zhao, Junhong,Wang, Hongli,Chen, Huan,Zhang, Yuhua,Gong, Sitang,Liu, Ruiyuan
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p. 809 - 815
(2018/02/09)
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- Synthetic method of novel fluorescence molecular probe PP for detecting lead ions
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The invention discloses a synthetic method of a novel fluorescence molecular probe PP for detecting lead ions. The fluorescence molecular probe PP comprises an identification group, a fluorophore anda connecting arm, wherein the identification group is co
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Paragraph 0024; 0030; 0034
(2018/07/30)
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- Full-color ultralong organic phosphorescent material as well as preparation method and application thereof
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The invention belongs to the field of preparation of pure organic phosphorescent materials and discloses a full-color ultralong organic phosphorescent material as well as a preparation method and application thereof, The full-color ultralong organic phosphorescent material is characterized in that phenothiazine chromophore is introduced into an electron-withdrawing group to realize an excitation light source-dependent pure organic ultralong phosphorescent material. The material has the following characteristics that the raw materials are low in price, and a synthetic method is simple and convenient; secondly, a synthesized material has long phosphorescence life and high quantum efficiency; thirdly, by changing the wavelength of an excitation light source, full-color ultralong organic phosphorescent emission from blue light to red light is realized. With special optical properties, the material has a potential application value in the fields of data encryption and full-color display.
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Paragraph 0064; 0065
(2018/03/25)
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- Efficient synthesis of phenothiazine-based heterocyclic derivatives and their biological studies
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Phenothiazine incorporated xanthene and 1,4-dihydropyridine derivatives were prepared by using N-alkyl-phenothiazine-3-carbaldehydes using one-pot reaction under reflux/ultrasonic irradiation. The synthesized compounds were characterized by using Fourier-transform infrared, 1H NMR, 13C NMR, and mass spectral data. Antibacterial activities of the synthesized compounds were screened against four different bacterial strains. The compound 5a and 5b showed good activity against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Bacillus cereus, and Klebsiella pneumoniae whereas compounds 4a and 4b show good activity against S. aureus and E. coli. The free radical-scavenging activities of synthesized compounds were screened, and the results were reported.
- Venkatesan,Satyanarayana,Sivakumar
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p. 367 - 372
(2018/09/29)
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- Nanosecond transient absorption spectroscopy of a Ru polypyridine phenothiazine dyad
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A bipyridine phenothiazine ligand [(PTZEtv2bpy) and metal complexes [Ru(Ph2phen)3]2+(1), [(Ph2phen)2Ru(PTZEtv2bpy)]2+(2), and [(PTZEtv2bpy)(Ph2ph
- Kosgei, Gilbert K.,Livshits, Maksim Y.,Canterbury, Theodore R.,Rack, Jeffery J.,Brewer, Karen J.
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supporting information
p. 67 - 70
(2016/11/22)
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- Near-infrared fluorescent dye based on phenothiazine as well as synthetic method and application of near-infrared fluorescent dye
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The invention relates to a near-infrared fluorescent dye based on phenothiazine. The chemical constitution of the near-infrared fluorescent dye based on phenothiazine is shown as the following formula (I). The near-infrared fluorescent dye is prepared by a condensation reaction of 10-ethylphenothiazine-3-formaldehyde and 4-(cyanomethyl)benzonitrile. The near-infrared fluorescent dye based on phenothiazine can perform fluorescent imaging on animal models with ulcer type proctopathy.
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Paragraph 0031
(2018/03/24)
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- Alkyl length dependent reversible mechanofluorochromism of phenothiazine derivatives functionalized with formyl group
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A series of D-A typed phenothiazine derivatives functionalized by formyl group (PCAn, n = 1, 2, 4 and 6) with different lengths of N-alkyl chains have been designed and synthesized to systematically investigate the effect of chain length on their solid-state fluorescence properties. The results showed that these compounds emitted strong fluorescence in solutions and solid states with 52%, 42%, 49% and 45% solid-state absolute fluorescence quantum yield (ΦF), respectively. Their emission wavelengths were strongly affected by solvent polarity, indicating intramolecular charge transfer (ICT) transitions. Interestingly, PCAn solids exhibit not only naked-eye visible and reversible mechanochromic behavior, but chain length-dependent emission properties. PCA1 shows smaller fluorescence spectrum shifts (22 nm) under mechanical force stimuli. Homologs with longer alkyl chains exhibit similar mechanochromic behaviors but larger fluorescence contrasts after grinding except for PCA6. Moreover, the fluorescence emission of ground solid PCA1 and PCA4 can recover at room temperature, PCA2 need high temperatures for fluorescence to be restored, and XRD and DSC revealed that the transformation between crystalline and amorphous states upon various external stimuli was responsible for the MFC behavior. This work demonstrates the feasibility of tuning the solid-state optical properties of fluorescent organic compounds by combining the simple alteration of chemical structure and the physical change of aggregate morphology under external stimuli.
- Jia, Junhui,Wu, Yuying
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p. 537 - 543
(2017/09/08)
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- LIQUID PHENOTHIAZINE CATHOLYTES FOR NON-AQUEOUS REDOX FLOW BATTERIES
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Highly soluble, liquid phenothiazines containing methoxy-terminated ether and oligoether substituents are disclosed with high diffusion coefficients and robust performance in electrochemical measurements, which can be synthesized in one step from commercially-available starting materials, thereby circumventing previous synthetic limitations.
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Paragraph 0015; 0033; 0048
(2017/06/21)
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- Hypochlorous acid fluorescent probe, as well as preparation method and application thereof
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The invention provides a hypochlorous acid fluorescent probe with quick response and high selectivity and sensitivity by molecular structure design, as well as a preparation method thereof and application of the hypochlorous acid fluorescent probe to detection of hypochlorous acid in an aqueous solution and a cell. The fluorescent probe can be applied to detection of the hypochlorous acid in the aqueous solution or a biological system, and detection comprises fluorescence detection, cell imaging and visual colorimetry. The fluorescence intensity forms linear positive correlation with the concentration of the hypochlorous acid within a certain concentration range, and the concentration of the hypochlorous acid can be quantitatively measured. The hypochlorous acid fluorescent probe is easy to synthesize, and a posttreatment process is relatively simple; selective and rapid detection of the hypochlorous acid molecular probe is realized, the selectivity is good, and the hypochlorite fluorescent probe is high in resistance to interference of other molecules, is a simple, rapid and sensitive hypochlorous acid molecular specific detection reagent, and has broad application prospect in the field of biomolecular detection.
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Paragraph 0020; 0024
(2017/10/13)
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- Elucidating the Excited State of Mechanoluminescence in Organic Luminogens with Room-Temperature Phosphorescence
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Two stable, purely organic luminogens exhibit both mechano- (ML) and photoluminescence (PL) with dual fluorescence–phosphorescence emissions at room temperature. Careful analysis of the crystal structures, coupled with theoretical calculations, demonstrate that room-temperature phosphorescence and ML properties are strongly related to molecular packing. In particular, the formation and fracture of molecular dimers with intermolecular charge-transfer properties has a significant effect on intersystem crossing, as well as excited triplet state emissions, in both PL and ML processes.
- Yang, Jie,Gao, Xuming,Xie, Zongliang,Gong, Yanbin,Fang, Manman,Peng, Qian,Chi, Zhenguo,Li, Zhen
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supporting information
p. 15299 - 15303
(2017/11/30)
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- Fluorescence probe for detecting hypochlorous acid and preparation method and application thereof
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The invention provides a rapidly-responsive hypochlorous acid fluorescence probe and an application of the fluorescence probe for detecting the hypochlorous acid in water solution or biological cells. While the fluorescence probe is applied for detecting HClO, the fluorescence probe reacts with the HClO, so the fluorescence is changed, a fluorescence peak value appears at 440 nm of the place, and the fluorescence intensity is positively correlated with the HClO concentration, so the existence of HClO is indicated or the HClO concentration is measured quantitatively. The fluorescence probe can be applied for the fluorescence detection and cell imaging in a biological system. Each synthesis process of the fluorescence probe is simple, the product extraction is simple, the specificity for the HClO is strong, various interferents are resisted, the rapid detection of the hypochlorous acid molecular probe is realized, the detection limit is low, the sensitivity is high, the linear range is wide, and the fluorescence probe has the extensive application prospect in the biomolecular detection field.
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Paragraph 0018; 0019
(2017/07/21)
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- Overcharge protection of lithium-ion batteries above 4 v with a perfluorinated phenothiazine derivative
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Electron-withdrawing substituents are introduced onto the phenothiazine core to raise its oxidation potential for use as a redox shuttle in high-voltage lithium-ion batteries. A perfluorinated derivative oxidizes at 4.3 V vs. Li+/0, and functio
- Kaur, Aman Preet,Casselman, Matthew D.,Elliott, Corrine F.,Parkin, Sean R.,Risko, Chad,Odom, Susan A.
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p. 5410 - 5414
(2016/05/24)
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- Phenothiazine derivative, preparation method and application thereof in dye-sensitized solar cells
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Belonging to the field of organic optoelectronic materials and organic photoelectric conversion application, the invention provides a phenothiazine pure organic dye, a preparation method and application thereof in dye-sensitized solar cells. The phenothiazine pure organic dye has a phenothiazine group, different functional groups are introduced to the N position of the phenothiazine group, and the phenothiazine group is connected to a carbazole group through meta-benzene, and the phenothiazine pure organic dye has a general formula shown as the specification, The dye provided by the invention can be applied to dye-sensitized solar cell devices to achieve high photoelectric conversion efficiency. The synthesis and preparation method involved in the invention is simple and controllable, and is low in cost, and the cell devices thereof have high efficiency. The phenothiazine pure organic dye is expected to replace traditional heavy metal sensitizing agent dyes, and has the application prospect of commercial production.
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Paragraph 0047-0052
(2017/06/14)
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- Reversible mechanochromic luminescence of phenothiazine-based 10,10′-bianthracene derivatives with different lengths of alkyl chains
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A series of 10,10′-bis(2-(N-alkylphenothiazine-3-yl)vinyl)-9,9′-bianthracene compounds (PVBAn, n = 2, 8, 12 and 16) with different lengths of N-alkyl chains have been designed and synthesized to systematically investigate the effect of chain length on their solid-state fluorescence properties. The results showed that these compounds emitted strong fluorescence in solution and in the solid state. Their emission wavelengths were also strongly affected by solvent polarity, indicating intramolecular charge transfer (ICT) transitions. Interestingly, the fluorescence emission and grinding-induced spectral shifts of PVBAn solids are alkyl length-dependent. PVBA2 shows the smallest fluorescence and absorption spectrum shifts under mechanical force stimuli. Homologues with longer alkyl chains exhibit similar mechanochromic behaviors and larger fluorescence contrasts after grinding. Moreover, the fluorescence emission of ground solid PVBA16 can recover at room temperature, but other compounds need high temperatures for fluorescence to be restored. Differential scanning calorimetry experiments reveal that the cold-crystallization temperature difference is responsible for thermal restoration behaviors. This work demonstrates the feasibility of tuning the solid-state optical properties of fluorescent organic compounds by combining the simple alteration of chemical structure and the physical change of aggregate morphology under external stimuli.
- Xue, Pengchong,Yao, Boqi,Liu, Xuhui,Sun, Jiabao,Gong, Peng,Zhang, Zhenqi,Qian, Chong,Zhang, Yuan,Lu, Ran
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p. 1018 - 1025
(2015/02/05)
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- An efficient ultrasound-assisted synthesis of n-alkyl derivatives of carbazole, indole, and phenothiazine
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Heterocyclic compounds bearing an acidic hydrogen atom attached to nitrogen such as carbazole, indole, and phenothiazine can be efficiently alkylated in DMSO or N,N-DMF under ultrasonic irradiation in the presence of potassium hydroxide as a base. In almost all cases, a dramatic reduction of the reaction time results and a clear yield increase accompanied by an improved quality of the products occurs.
- Zhao, Sanhu,Kang, Jin,Du, Yuting,Kang, Jingyan,Zhao, Xiaoni,Xu, Yinfeng,Chen, Ruixi,Wang, Qianqian,Shi, Xitao
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supporting information
p. 683 - 689
(2014/06/10)
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- Piezofluorochromic properties of AIE-active 9,10-bis(N-alkylpheno-thiazin- 3-yl-vinyl-2)anthracenes with different length of alkyl chains
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9,10-Bis(N-alkylphenothiazin-3-yl-vinyl-2)anthracenes (PT-Cn) with different carbon numbers (n) of alkyl chains (n = 2, 3, 5, 6, 7, 9, 12, 18) are prepared to further understand the effect of alkyl lengths on the solid-state fluorescence and piezochromic luminescence of alkyl-containing 9,10-bis(arylvinyl)anthracenes. The results show that the fluorescence emissions of both pressed and annealed PT-Cn are gradually blue-shifted, but the blue-shifted amplitudes of annealed states are more remarkable with the increase of alkyl length, leading to that longer alkyl-containing PT-Cn show larger piezofluorochromism (PFC) spectral shifts. Powder wide-angle X-ray diffraction and differential scanning calorimetry experiments reveal that the transformation between crystalline and amorphous states under various external stimuli is responsible for the PFC and restoration behaviors. This work demonstrates once again that combining the simple alternation of molecular chemical structure and the physical change of aggregate morphology under external stimuli could tune the solid-state optical properties of some organic fluorophores.
- Zheng, Meng,Sun, Mingxiao,Li, Yiping,Wang, Jianfeng,Bu, Lingyu,Xue, Shanfeng,Yang, Wenjun
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- Overcharge performance of 3,7-disubstituted N-ethylphenothiazine derivatives in lithium-ion batteries
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3,7-Disubstituted N-ethylphenothiazine derivatives were synthesized as redox shuttle candidates for lithium-ion batteries. Battery cycling results show that three derivatives prevent overcharge. the Partner Organisations 2014.
- Ergun, Selin,Elliott, Corrine F.,Kaur, Aman Preet,Parkin, Sean R.,Odom, Susan A.
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supporting information
p. 5339 - 5341
(2014/05/06)
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