- Hybrids of a 9-anthracenyl moiety and fluorescein as chemodosimeters for the detection of singlet oxygen in live cells
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Singlet oxygen (1O2) plays an important role in human innate immune response, plant physiology and anticancer photodynamic therapy (PDT). Therefore, its monitoring by convenient and sensitive methods (e.g. by detecting a fluorescence signal) by using non-toxic reagents would be advantageous. Known fluorogenic 1O2-chemodosimeters can potentially consume reducing agents in cells leading to the generation of toxic side products that limit their applications. In this paper we report on a series of 9-anthracenyl-fluorescein hybrids, which do not require any reducing agents for their reaction with 1O2. The selected compound 8d at a very low concentration of 100 nM is able to detect 1O2 in live human promyelocytic leukemia HL-60 cells with over 35-fold fluorescence signal enhancement within only 20 min assay time. This chemodosimeter is not toxic to HL-60 cells at concentrations ≤1 μM (higher concentrations were not tested) even at long incubation times ≤48 h.
- Chercheja, Serghei,Daum, Steffen,Xu, Hong-Gui,Beierlein, Frank,Mokhir, Andriy
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- Preparation method of anthraquinone and alkyl derivatives thereof
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The invention relates to the field of organic matter preparation, and discloses a preparation method of anthraquinone and alkyl derivatives thereof, and the method comprises the following steps: underacidic conditions, carrying out contact reaction on anthracene and alkyl derivatives thereof, an oxidant and a catalyst. The anthraquinone and the alkyl derivative thereof have a structure as shown in a formula (I) which is described in the specification. The catalyst comprises a carrier and metal elements loaded on the carrier, wherein the metal elements comprise molybdenum and tungsten, in theformula (I), R1 and R2 are each independently selected from hydrogen and substituted or unsubstituted C1-C10 hydrocarbon groups. The method provided by the invention has the characteristics of mild operation conditions and high product yield.
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Paragraph 0139-0142; 0145-0154
(2020/08/18)
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- Synthesis and electronic properties of sterically demanding N-arylphenothiazines and unexpected Buchwald-Hartwig aminations
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(Chemical Equation Presented) Phenothiazine is coupled under Buchwald-Hartwig conditions with bromo anthracenes and perylene as substrates to give phenothiazine-anthracene and phenothiazine-perylene dyads and triads. Investigation of the electronic properties of these sterically demanding N-aryl phenothiazines by absorption and emission spectroscopy, cyclic voltammetry, and DFT calculations revealed that the individual chromophores are decoupled in the electronic ground state but show unique electronic communication in the excited state. For the anthracenyl-bridged diphenothiazine an intense electronic coupling of the phenothiazinyl units is detected upon oxidation. Besides, attempts to synthesize phenothiazine compounds with even more sterically demanding aryl substituents in the 10-position under N-arylation conditions gave rise to the formation of quite unexpected products of arylation and/or oxidative coupling. The folding angle of the phenothiazine in a consanguineous series correlates well with the first oxidation potential.
- Franz, Adam W.,Rominger, Frank,Mueller, Thomas J. J.
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p. 1795 - 1802
(2008/09/18)
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- NOVEL SOLUBLE COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICES
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A novel soluble compound which is a distyrylarylene derivative having a soluble substituent and a specific central group and having a solubility of 0.5% by weight or greater at 20°C in an organic solvent; and an organic electroluminescence device having an organic thin film layer which has a single layer or a plurality of layers, is disposed between a cathode and an anode and has at least one layer containing the novel soluble compound. The organic thin film layer can be formed in accordance with a wet process, and the organic electroluminescence device exhibiting a great efficiency of light emission can be produced easily.
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- Synthesis of Alkyl-Substituted Helianthrones and Mesonaphthobianthrone by Highly Regioselective Photocyclization of Bianthronylidenes
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The synthesis of the novel alkyl-substituted helianthrones 8a, c and mesonaphthobianthrone 9 by photocyclization of the corresponding bianthronylidenes 7a, b is described.Regioselectivity and scope of the photocyclizations of 7a and 7b depend on the substitution pattern.The structures of 7a and 8a have been established by X-ray crystallography and indicate an isomerization about the central double bond of 7a in the photoreaction.The structures of the protonated species of 8a and 9 are elucidated, and their optical absorption and emission behavior is examined.Key Words: Bianthronyls / Bianthronylidenes / Helianthrone / Mesonaphthobianthrone / Photocyclization
- Mueller, Uwe,Enkelmann, Volker,Adam, Martin,Muellen, Klaus
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p. 1217 - 1226
(2007/10/02)
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- SYNTHESIS OF SUBSTITUTED tert-BUTYLANTHRAQUINONES
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The oxidation of 2-methyl-5-tert-butyldiphenylmethane and its 4'-methyl-, chloro-, and nitro-substituded derivatives by potassium permangate in a mixture of pyridine and water leads to the formation of the correspoding 2-benzoyl-4-tert-butyl-benzoic acids, which are converted by the action of sulfuric acid with heat into substituted 2-tert-butylanthraquinones.The cyclization of 2-benzoyl-4-tert-butylbenzoic acids containig a tert-butyl group or chlorine atom in the benzoyl ring is accompanied by a Hayashi rearrangement, which leads to the formation of mixtures thecorresponding 2,6- and 2,7-disubstituted anthraquinones.
- Pozdnyakovich, Yu. V.,Savyak, R. P.,Shein, S. M.
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p. 532 - 538
(2007/10/02)
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- ALKYLATION OF ANTHRACENE BY tert-BUTYL ALCOHOL
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The alkylation of anthracene by tert-butyl alcohol in the presence of trifluoro acetic acid or Lewis acids leads to the formation of 2-tert-butylanthracene and 2,6- and 2,7-di-tert-butylanthracenes.The ratio of 2,6- and 2,7-di-tert-butylanthracenes formed in the presence of trifluoroacetic acid and titanium tetrachloride is close to 75:25 and is determined by the relative alkylation rates of 2-tert-butylanthracene at positions 6 and 7.In the presence of aluminum chloride the ratio of the isomeric di-tert-butylanthracenes is 50:50 and is established as a result of the disproportionation and isomerization of the alkylation products.
- Pozdnyakovich, Yu.V.
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p. 527 - 531
(2007/10/02)
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