21667-32-3Relevant academic research and scientific papers
Boronate ester cross-linked PVA hydrogels for the capture and H2O2-mediated release of active fluorophores
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.
, p. 5516 - 5519 (2020)
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.
Solution Structure and Preferred Orientation of 3,7-Dibromo-10H-phenothiazine Dissolved in Nematic Liquid Crystal
Fujiwara, Hideaki,Watanabe, Masayuki,Yamanaka, Iwao,Takagi, Tatsuya,Sasaki, Yoshio
, p. 369 - 374 (1988)
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.
Characterisation of 3,7-dibromophenothiazin-5-ium perbromide and its use for enhancing latent fingerprints
Plater, John,Harrison, William T. A
, p. 384 - 387 (2009)
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-
Antitubercular polyhalogenated phenothiazines and phenoselenazine with reduced binding to CNS receptors
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
, (2020)
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.
[1]Benzothieno[3,2-b]benzothiophene-Based Organic Dyes for Dye-Sensitized Solar Cells
Capodilupo, Agostina L.,Fabiano, Eduardo,De Marco, Luisa,Ciccarella, Giuseppe,Gigli, Giuseppe,Martinelli, Carmela,Cardone, Antonio
, p. 3235 - 3245 (2016)
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.
5,5-Dioxoyphenothiazine-based D-A-D type AIE molecules enabling persistent room temperature phosphorescence, white light emission and dual-mode mechanochromism
Zhou, Xiaolu,Xu, Songlin,Liu, Liqiang,Sun, Yiping,Cheng, Jinxi,Duan, Xingyu,Zhou, Lishan,Qu, Hongmei
, (2021)
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.
Synthesis of substituted phenothiazines analogous to methylene blue by electrophilic and nucleophilic aromatic substitutions in tandem. A mechanistic perspective
Leventis, Nicholas,Chen, Muguo,Sotiriou-Leventis, Chariklia
, p. 10083 - 10092 (1997)
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.
On the Road Toward More Efficient Biocompatible Two-Photon Excitable Fluorophores
Auvray, Marie,Bolze, Frédéric,Naud-Martin, Delphine,Poulain, Matthieu,Bossuat, Margaux,Clavier, Gilles,Mahuteau-Betzer, Florence
supporting information, (2022/02/17)
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.
HIGH TRIPLET YIELD PHENOTHIAZINE DONOR-ACCEPTOR COMPLEXES FOR PHOTOREDOX CATALYSIS
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Page/Page column 35, (2021/07/17)
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,
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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Paragraph 0147-0149, (2020/08/26)
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.
