- Boronate ester cross-linked PVA hydrogels for the capture and H2O2-mediated release of active fluorophores
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A new set of PVA hydrogels were formed using the boronate ester fluorescent probe PF1 and the novel boronate fluorescent probe PT1 as the covalent crosslinkers. Treatment with aqueous H2O2 allowed triggered release of the fluorescent dye accompanied by complete dissolution of the hydrogel.
- Williams, George T.,Sedgwick, Adam C.,Sen, Sajal,Gwynne, Lauren,Gardiner, Jordan E.,Brewster, James T.,Hiscock, Jennifer R.,James, Tony D.,Jenkins, A. Toby A.,Sessler, Jonathan L.
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- Solution Structure and Preferred Orientation of 3,7-Dibromo-10H-phenothiazine Dissolved in Nematic Liquid Crystal
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The NMR spectrum of the title compound has been measured in nematic phase ZLI1167 and analyzed to obtain the direct couplings.The direct couplings were interpreted by assuming a folded structure of the tricyclic framework.The dihedral angle of the two phenyl rings is determined to be 149+/-2.5 deg and a value 170+/-3 deg is obtained for the angle of S...N-H.The NH proton is concluded to occupy a "equatorial" position on the central ring in a boat form.The preferred orientation of the molecule in ZLI1167 is discussed by comparing the principal axes order tensor with those of the moment of inertia.
- Fujiwara, Hideaki,Watanabe, Masayuki,Yamanaka, Iwao,Takagi, Tatsuya,Sasaki, Yoshio
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- Characterisation of 3,7-dibromophenothiazin-5-ium perbromide and its use for enhancing latent fingerprints
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Solutions were formulated by dissolving 3,7-dibromophenothiazin-5-ium perbromide in primary and secondary alcohols with pyridine as base. These solutions were used as dips for the enhancement of latent fingerprints. Treatment of 3,7-dibromophenothiazin-5-
- Plater, John,Harrison, William T. A
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- Antitubercular polyhalogenated phenothiazines and phenoselenazine with reduced binding to CNS receptors
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Targeting energy metabolism in Mycobacterium tuberculosis (Mtb) is a new paradigm in the search for innovative anti-TB drugs. NADH:menaquinone oxidoreductase is a non-proton translocating type II NADH dehydrogenase (NDH-2) that is an essential enzyme in the respiratory chain of Mtb and is not found in mammalian mitochondria. Phenothiazines (PTZs) represent one of the most known class of NDH-2 inhibitors, but their use as anti-TB drugs is currently limited by the wide range of potentially serious off-target effects. In this work, we designed and synthesized a series of new PTZs by decorating the scaffold in an unconventional way, introducing various halogen atoms. By replacing the sulfur atom with selenium, a dibromophenoselenazine 20 was also synthesized. Among the synthesized poly-halogenated PTZs (HPTZs), dibromo and tetrachloro derivatives 9 and 11, along with the phenoselenazine 20, emerged with a better anti-TB profile than the therapeutic thioridazine (TZ). They targeted non-replicating Mtb, were bactericidal, and synergized with rifampin and bedaquiline. Moreover, their anti-TB activity was found to be related to the NDH-2 inhibition. Most important, they showed a markedly reduced affinity to dopaminergic and serotonergic receptors respect to the TZ. From this work emerged, for the first time, as the poly-halogenation of the PTZ core, while permitting to maintain good anti-TB profile could conceivably lead to fewer CNS side-effects risk, making more tangible the use of PTZs for this alternative therapeutic application.
- Barreca, Maria Letizia,Bojarski, Andrzej J.,Cecchetti, Violetta,Cook, Gregory M.,Desantis, Jenny,Felicetti, Tommaso,Franzblau, Scott G.,Handzlik, Jadwiga,Hards, Kiel,Latacz, Gniewomir,Manfroni, Giuseppe,Massari, Serena,Mazzarella, Maria Angela,Nakatani, Yoshio,Nizi, Maria Giulia,Rushton-Green, Rowena,Sabatini, Stefano,Shetye, Gauri,Tabarrini, Oriana,Kolá?, Michal H.,Sata?a, Grzegorz
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- [1]Benzothieno[3,2-b]benzothiophene-Based Organic Dyes for Dye-Sensitized Solar Cells
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Three new metal-free organic dyes with the [1]benzothieno[3,2-b]benzothiophene (BTBT) π-bridge, having the structure donor-π-acceptor (D-π-A) and labeled as 19, 20 and 21, have been designed and synthesized for application in dye-sensitized solar cells (DSSC). Once the design of the π-acceptor block was fixed, containing the BTBT as the π-bridge and the cyanoacrylic group as the electron acceptor and anchoring unit, we selected three donor units with different electron-donor capacity, in order to assemble new chromophores with high molar extinction coefficients (?), whose absorption features well reflect the good performance of the final DSSC devices. Starting with the 19 dye, which shows a molar extinction coefficient ? of over 14,000 M-1 cm-1 and takes into account the absorption maximun at the longer wavelength, the substitution of the BFT donor unit with the BFA yields a great enhancement of absorptivity (molar extinction coefficient ? > 42,000 M-1 cm-1), until reaching the higher value (? > 69,000 M-1 cm-1) with the BFPhz donor unit. The good general photovoltaic performances obtained with the three dyes highlight the suitable properties of electron-transport of the BTBT as the π-bridge in organic chromophore for DSSC, making this very cheap and easy to synthesize molecule particularly attractive for efficient and low-cost photovoltaic devices.
- Capodilupo, Agostina L.,Fabiano, Eduardo,De Marco, Luisa,Ciccarella, Giuseppe,Gigli, Giuseppe,Martinelli, Carmela,Cardone, Antonio
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- 5,5-Dioxoyphenothiazine-based D-A-D type AIE molecules enabling persistent room temperature phosphorescence, white light emission and dual-mode mechanochromism
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Novel heavy atom free 5,5-dioxoyphenothiazine-based “D–A–D” emitters with aggregation-induced emission (AIE), room-temperature phosphorescence (RTP), white light emission and dual-mode mechanochromic luminescence (MCL) characteristics have been designed and synthesized. Impressively, DCzCs and DCzCs-Et showed persistent RTP (pRTP) in the crystalline state with lifetimes of 528 ms and 137 ms in air, respectively. DCzCs-Ac exhibited white light emission with a CIE coordinate of (0.25, 0.26), due to the dual emission of fluorescence and phosphorescence. Detailed studies have shown that through simply functional group modification on the acceptor skeleton to modulate the molecular structure and intermolecular interactions, we fine-tuned the optical properties of the luminogens and realized white light emission. The dense crystal packing was proved to be closely related to the phosphorescence of the system and the special dual-mode MCL behavior was attributed to the conversion of crystalline-amorphous state under external force.
- Zhou, Xiaolu,Xu, Songlin,Liu, Liqiang,Sun, Yiping,Cheng, Jinxi,Duan, Xingyu,Zhou, Lishan,Qu, Hongmei
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- Synthesis of substituted phenothiazines analogous to methylene blue by electrophilic and nucleophilic aromatic substitutions in tandem. A mechanistic perspective
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3,7-Disubstituted phenothiazines analogous to methylene blue (1) were synthesized from phenothiazine (6) reacting first with an excess of bromine in acetic acid to give 3,7-dibromophenothiazin-5-ium bromide (8), according to a reaction sequence that involves two electrophilic aromatic substitutions and one oxidation. Subsequently, 8 reacting with diallylamine or allylmethylamine via two nucleophilic aromatic substitution steps gave 3,7-bis[di(2-propenyl)amino]phenothiazin-5-ium bromide (3) or 3,7-bis[methyl, (2-propenyl)amino]phenothiazin-5-ium bromide (4), compounds analogous to methylene blue. The choice of solvent for the second step is critically important as 3,7-dibromophenothiazin-5-ium bromide is very reactive and prone to irreversible oxidation, reduction, and ipso attack at the 3- and 7- positions. The best yields (~63%) for the methylene blue analogues 3 and 4 were obtained when CHCl3 or CH2Cl2 were employed as solvents for the nucleophilic aromatic substitution step. These solvents dissolve the methylene blue analogue products, but not 3,7-dibromophenothiazin-5-ium bromide.
- Leventis, Nicholas,Chen, Muguo,Sotiriou-Leventis, Chariklia
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- On the Road Toward More Efficient Biocompatible Two-Photon Excitable Fluorophores
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Red-to-NIR absorption and emission wavelengths are key requirements for intravital bioimaging. One of the way to reach such excitation wavelengths is to use two-photon excitation. Unfortunately, there is still a lack of two-photon excitable fluorophores that are both efficient and biocompatible. Thus, we design a series of biocompatible quadrupolar dyes in order to study their ability to be used for live-cell imaging, and in particular for two-photon microscopy. Hence, we report the synthesis of 5 probes based on different donor cores (phenoxazine, acridane, phenazasiline and phenothiazine) and the study of their linear and non-linear photophysical properties. TD-DFT calculations were performed and were able to highlight the structure-property relationship of this series. All these studies highlight the great potential of three of these biocompatible dyes for two-photon microscopy, as they both exhibit high two-photon cross-sections (up to 3650 GM) and emit orange to red light. This potential was confirmed through live-cell two-photon microscopy experiments, leading to images with very high brightness and contrast.
- Auvray, Marie,Bolze, Frédéric,Naud-Martin, Delphine,Poulain, Matthieu,Bossuat, Margaux,Clavier, Gilles,Mahuteau-Betzer, Florence
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supporting information
(2022/02/17)
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- HIGH TRIPLET YIELD PHENOTHIAZINE DONOR-ACCEPTOR COMPLEXES FOR PHOTOREDOX CATALYSIS
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Phenothiazine compounds of Formula (I) are described herein. These compounds are useful as highly reducing organic photoredox catalysts. Suitable substrates for use with the compounds of Formula (I) include acrylates, styrene, acrylamides, acrylonitrile,
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Page/Page column 35
(2021/07/17)
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- Dendritic bipolar main body material taking triazine as central core, and preparation method and application of dendritic bipolar main body material in organic electroluminescent device
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The invention provides a compound with a structure represented by a formula (I) and a preparation method and application thereof. The compound with the structure represented by the formula (I) is a dendritic bipolar main body material taking triazine as a central core, the structure is different from a D-pi-A type structure of a traditional dendritic bipolar main body; the central core triazine isused as an electron acceptor (A), peripheral branches are used as electron donors (D), and a D-A type dendritic bipolar main body formed by direct connection of the donors and the acceptors maintainsa high triplet state energy level (2.8-3.3 eV), so that the application of the bipolar main body to a blue light OLED device is facilitated; it is found through experiments that the maximum current efficiency of a blue phosphorus photoluminescence device prepared with the compound as a main body material can reach 46.7 cd/A, the maximum power efficiency can reach 50.11 m/W, the maximum brightnesscan reach 32000 cd/m, and the turn-on voltage is 2.4 V.
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Paragraph 0147-0149
(2020/08/26)
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- Thermally activated delayed fluorescent dendritic host material using triarylphosphine oxide as central core, preparation method and organic electroluminescent device
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The invention provides a thermally activated delayed fluorescent dendritic host material using triarylphosphine oxide as a central core, a preparation method and an organic electroluminescent device and belongs to the field of organic semiconductor photoe
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Paragraph 0134-0136
(2019/10/02)
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- Novel phenothiazine derivatives and organic electronic devices containing them
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The present invention provides a novel phenothiazine derivative and an organic electronic device containing the same, and more specifically, to a novel phenothiazine derivative contained in a buffer layer capable of alleviating polarity difference between a photoactive layer and an electron transport layer, and to an organic electronic device including the novel phenothiazine derivative.COPYRIGHT KIPO 2018
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Paragraph 0087; 0089; 0093; 0094
(2018/03/01)
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- ANTI-INFECTIVE HETEROCYCLIC COMPOUNDS AND USES THEREOF
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The present invention relates to heterocyclic compounds of Formula I useful as anti-infective agents. The present invention further relates to a method of treating an infection by administering such compounds, and to pharmaceutical compositions comprising such compounds.
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Page/Page column 8; 9; 71; 72
(2018/04/11)
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- Flexible chain structure-containing host material and organic light-emitting device
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The invention provides a flexible chain structure-containing host material and an organic light-emitting device, belonging to the technical field of organic optoelectronic materials and solving the technical problem in the prior art that the organic optoelectronic materials have poor luminescent properties such as low luminous efficiency. The flexible chain structure-containing host material has the beneficial effects that electron withdrawing groups and electron-donating groups are connected by flexible chains to break conjugate connection between the electron withdrawing groups and the electron-donating groups, thereby substantially improving triplet state energy level; and the organic light-emitting device prepared by using the flexible chain structure-containing host material has a good luminescent property, the luminous efficiency of up to 10.8cd/A and the driving voltage of up 3.1V and is an excellent OLED (Organic Light Emitting Diode) material.
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Paragraph 0049; 0050
(2017/09/01)
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- Podands with 3,7,10-trisubstituted phenothiazine units: Synthesis and structural analysis
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The synthesis of 10H-phenothiazine dipodands exhibiting -CH2-OH or -CHO reactive groups at positions 3 and 7, suitable for macrocyclization reactions, as well as -CH2COOtBu or -CH2CH2CN groups at position 10, wh
- Rednic, Monica Irina,Szima, Szabolcs,Bogdan, Elena,H?dade, Niculina D.,Terec, Anamaria,Grosu, Ion
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p. 637 - 642
(2015/11/24)
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- Multiple fluorescent behaviors of phenothiazine-based organic molecules
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We have designed a conventional one-step Suzuki coupling synthetic method to prepare 3,7-di-aryl substituted 10H-phenothiazine derivatives and investigated their optical behaviors. The compound 3,7-Bis (4-aminophenyl) phenothiazine (compound 1), substituting with electron-donating aniline, can exhibit photodamage behavior toward cancer cells. Furthermore, the compound 1 can form fluorescent organic nanoparticle (FON) in acidic aqueous whereas can emit red fluorescence in alkaline organic solvent. More importantly, compound 1 can be oxidized to manufactured a stable near-IR dye (>950 nm). Alternatively, the control compound 3,7-Bis (4-nitrophenyl) phenothiazine (compound 2) enabled us to determine that an electron-withdrawing group, when attaching on the phenothiazine, is unfavorable for molecular design to manufacture a cation form of NIR dye but is favorable to stabilize the phenothiazinate core and manufacture an anion form of NIR dye.
- Hsieh, Tung-Sheng,Wu, Jhen-Yi,Chang, Cheng-Chung
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- DERIVATIVES OF SQUARAINE, DYE FOR DYE-SENSITIZED SOLAR CELLS AND DYE-SENSITIZED SOLAR CELLS
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The present invention refers to [...] derivatives, dye-sensitized solar cell for dye and dye sensitized solard cell relates to, high yield of dyestuffs [...] derivatives represented by formula 1, excellent light conversion efficiency, and in which a large
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Paragraph 0190-0192; 0194; 0195
(2016/12/01)
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- Evaporable organic semiconductive material and use thereof in an optoelectronic component
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The invention relates to compounds of general formula IIIa and their use in optoelectronic components.
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Page/Page column 35; 36; .37
(2015/10/05)
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- Synthesis of a photostable near-infrared-absorbing photosensitizer for selective photodamage to cancer cells
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A new class of near-infrared (NIR)-absorptive (>900 nm) photosensitizer based on a phenothiazinium scaffold is reported. The stable solid compound, o-DAP, the oxidative form of 3,7-bis(4-methylaminophenyl)-10H-phenothiazine, can generate reactive oxygen species (ROS, singlet oxygen and superoxide) under appropriate irradiation conditions. After biologically evaluating the intracellular uptake, localization, and phototoxicity of this compound, it was concluded that o-DAP is photostable and a potential selective photodynamic therapy (PDT) agent under either NIR or white light irradiation because its photodamage is more efficient in cancer cells than in normal cells and is without significant dark toxicity. This is very rare for photosensitizers in PDT applications. Selective PDT agent: A photostable near-infrared (NIR)-absorptive phenothiazinium derivative, o-DAP, has been successfully synthesized and demonstrated to be a potential tumor-specific NIR-absorptive (>900 nm) photosensitizer for photodynamic therapy (PDT; see figure). This compound is expected to become a PDT reagent in a solar environment.
- Hsieh, Tung-Sheng,Wu, Jhen-Yi,Chang, Cheng-Chung
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supporting information
p. 9709 - 9715
(2014/08/18)
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- Antiviral Compounds
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Novel compounds, methods, and compositions for treating various viral infections are described. In some embodiments the novel compounds of the invention are 3-oxo-phenothiazine derivatives; more specific embodiments include 3-oxo-phenothiazine derivatives having substituents at the 1-, 7-, and 9-positions of the phenothiazine parent ring. In other embodiments, the invention provides compositions and methods for treating viral infections, especially HIV.
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(2012/09/25)
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- Fluorescent organic nanoparticle formation in lysosomes for cancer cell recognition
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We present a convenient method to prepare fluorophores 3- or 3,7-divinyl substituted 10H-phenothiazines and their protonation forms can aggregate to become fluorescent organic nanoparticles (FONs) with bright fluorescent spots in the lysosomes of cancer cells but not normal cells.
- Lin, Hsin-Hung,Su, Sheng-Yuan,Chang, Cheng-Chung
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supporting information; experimental part
p. 2036 - 2039
(2009/09/04)
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- Reaction of π-Deficient Aromatic Heterocycles with Ammonium Polyhalides III [1]. Halogenation of Phenothiazin-5-oxide with Benzyltriethylammonium Polyhalides
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Halogenation of phenothiazin-5-oxide with benzyltriethylammonium polyhalides (BTEA) under mild conditions afforded chloro- and bromophenothiazines as well as a few unexpected products e.g. 1,3,7,9-tetrachloro-phenothiazin-5-oxide, 7,3′-dibromo-3, 10′-diphenothiazinyl tribromide, and 7,3′-dichloro-3,10′-diphenothiazinyl tetrachloroiodate. A new charge-transfer complex of phenothiazine-5-oxide with bromine is reported.
- Custelceanu,Vlassa,Silberg
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p. 919 - 925
(2007/10/03)
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