1637-16-7Relevant articles and documents
Tuning the optoelectronic properties of phenothiazine-based D?A-type emitters through changing acceptor pattern
Qiu, Xu,Shi, Jinjin,Xu, Xin,Lu, Yuansheng,Sun, Qikun,Xue, Shanfeng,Yang, Wenjun
, p. 6 - 15 (2017)
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
Phenothiazine and diphenylsulfone-based donor–acceptor π-systems exhibiting remarkable mechanofluorochromism
Feng, Xiucun,Fu, Shengjie,Huang, Qian,Liu, Xingliang,Xu, Defang,Zhang, Weidong,Zhang, Zhan,Zhou, Hongke
, (2021)
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).
Phenothiazine-based organic dyes with two anchoring groups on TiO 2 for highly efficient visible light-induced water splitting
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
, p. 11431 - 11433 (2012)
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.
Observation of peroxynitrite overproduction in cells during 5-fluorouracil treatment: Via a ratiometric fluorescent probe
Cao, Xinhua,Cui, Beibei,Hou, Ji-Ting,Wang, Bingya,Wang, Shan,Ye, Yong,Zhang, Man,Zhang, Yongru
, p. 2759 - 2762 (2020)
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.
Two novel fluorescent probes based on phenothiazine: synthesis and “naked-eye” colorimetric recognition of Hg2+
Wang, Chuane,Wang, Lizhen,Fang, Shimin,Qin, Dawei,Zhou, Jianhua,Yang, Geng,Jin, Shuangshuang,Duan, Hongdong
, p. 2045 - 2063 (2019)
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.
Novel cyanoacetamide integrated phenothiazines: Synthesis, characterization, computational studies and in vitro antioxidant and anticancer evaluations
Krishnan, Kannan Gokula,Kumar, Chandran Udhaya,Lim, Wei-Meng,Mai, Chun-Wai,Thanikachalam, Punniyakoti V.,Ramalingan, Chennan
, (2020)
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.
Efficient red fluorescent OLEDs based on aggregation-induced emission combined with hybridized local and charge transfer state
Cang, Miao,Cui, Wei,Sun, Mizhen,Wang, Runze,Xu, Lei,Xue, Shanfeng,Yang, Wenjun,Yu, Yuan,Zhou, Huayi
, (2021)
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.
Phenacyl Phenothiazinium Salt as a New Broad-Wavelength-Absorbing Photoinitiator for Cationic and Free Radical Polymerizations
Liu, Ren,Xu, Dandan,Yagci, Yusuf,Zhang, Yuchao,Zhou, Yufan,Zhu, Yi
, p. 16917 - 16921 (2021)
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.
Phase transfer catalysis in N-alkylation of the pharmaceutical intermediates phenothiazine and 2-chlorophenothiazine
Gozlan,Ladkani,Halpern,et al.
, p. 613 - 614 (1984)
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Yarmukhametova,D.Kh. et al.
, (1972)
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Two novel two-photon polymerization initiators with extensive application prospects
Tian, Yupeng,Zhang, Mingliang,Yu, Xiaoqiang,Xu, Guibao,Ren, Yan,Yang, Jiaxiang,Wu, Jieying,Zhang, Xuanjun,Tao, Xutang,Zhang, Shengyi,Jiang, Minhua
, p. 325 - 329 (2004)
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
A new phenothiazine-based fluorescence sensor for imaging Hg2+ in living cells
Sun, Yucheng,Wang, Lizhen,Zhou, Jianhua,Qin, Dawei,Duan, Hongdong
, (2020)
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.
Phenothiazine-based benzoxazole derivates exhibiting mechanochromic luminescence: The effect of a bromine atom
Xue, Pengchong,Yao, Boqi,Sun, Jiabao,Xu, Qiuxia,Chen, Peng,Zhang, Zhenqi,Lu, Ran
, p. 3942 - 3950 (2014)
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.
Effect of a bridge unit on the mechanochromism of phenothiazine-based Schiff bases
Yang, Zicheng,Xue, Pengchong,Zhang, Lulu,Chen, Peng
, p. 14603 - 14608 (2019)
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.
A novel highly sensitive and selective fluorescent sensor for imaging mercury(ii) in living cells
Zhou, Chen,Song, Yan,Li, Yapeng
, p. 33614 - 33618 (2014)
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.
Design synthesis and property research based on phenothiazine reversible fluorescent probe
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Paragraph 0018-0019, (2021/12/07)
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.
