84-54-8Relevant articles and documents
Photoinduced electron transfer between 2-methylanthraquinone and triethylamine in an ionic liquid: Time-resolved EPR and transient absorption spectroscopy study
Zhu, Guanglai,Wang, Yu,Fu, Haiying,Xu, Xinsheng,Cui, Zhifeng,Ji, Xuehan,Wu, Guozhong
, p. 148 - 153 (2015)
Photoinduced electron transfer between 2-methylanthraquinone (MeAQ) and triethylamine (TEA) in a room-temperature ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF6]), was investigated by comparing the time-resolved electron paramagnetic resonance (TR-EPR) spectroscopy and the transient absorption spectroscopy. The results of TR-EPR spectroscopy, in which MeAQ was 8 mmol L-1and TEA was 150 mmol L-1, indicated that the transient radical would exist longer time in [bmim][PF6] than in acetonitrile. At the delay time of 8 μs after laser excitation, the TR-EPR signal transformed from an emissive peak into an absorptive peak when the experiment was performed in [bmim][PF6]. The results of the transient absorption spectroscopy, in which MeAQ was 0.1 mmol L-1and TEA was 2.2 mmol L-1, showed that the efficiency and the rate of the photoinduced electron transfer reaction in [bmim][PF6] were obviously lower than that in acetonitrile. It was concluded that various factors, such as concentration, viscosity and local structural transformation of the solution, have an influence on the process of photoinduced electron transfer in [bmim][PF6].
Electroreductive Cleavage of Substituted 9,10-Anthraquinones in 50percent Aqueous THF Buffers: A pH-Dependent Process
Blankespoor, Ronald L.,Hsung, Richard,Schutt, David L.
, p. 3032 - 3035 (1988)
A variety of substituted 9,10-anthraquinones with acetate leaving groups (4a-7a) were reduced at a glassy carbon electrode in 50percent aqueous THF prepared from aqueous buffers at pH 6, 7, and 8.Cyclic voltammograms of these compounds exhibited a single reduction wave with Ep values of -450 to -530 mV (vs Ag/AgCl/0.10 M Cl-) at pH 7.Ep shifted to more negative values with increasing pH (45-50 mV/pH unit) consistent with a 2e-/2H+ reduction process which converts 4a-7a to their corresponding anthrahydroquinones.Constant potential reduction of acetates 4a-7a at -800 mV at pH 6 or 7 gave n values of 2.2-2.4.Air oxidation of the catholytes, a procedure that converts anthrahydroquinones to anthraquinones, led to a 56-89percent recovery of the acetates and 7-32percent yields of the reductive cleavage products 4b-7b.In contrast, electroreduction of 4a-7a at pH 8 gave much higher yields (50-73percent) of 4b-7b with n values of 3.5-3.8.This pH-dependent process suggests that 4a-7a cleave much slower via their intermediate anthrahydroquinones than the conjugate bases of their anthrahydroquinones, which are present in relatively high concentration at higher pH.NaOH titration curves of the anthrahydroquinones of 5a and 5b support this mechanistic picture.
(E)-2-Styrylanthracene-9,10-dione: A new type of fluorescent probe core and its application in specific mitochondria imaging
Lu, Peng-fei,Meng, Fan-hao,Wang, Lin,Wang, Qiu-yin,Wang, Zhao-ran,Zhang, Ting-jian,Zhang, Xu,Zhao, Hai-yang
, (2021/09/20)
Herein, a new type of fluorescent probe core, (E)-2-styrylanthracene-9,10-dione (EK01), was developed which displayed strong fluorescence quantum yield (Φ = 0.867 in DMF; Φ = 0.561 in acetone; Φ = 0.616 in CH2Cl2; Φ = 0.265 in DMSO), good photostability, large stokes shift (90 nm–120 nm) and molar extinction coefficients (0.5875 × 104–0.7609 × 104 mol?1 L cm?1). During cell assays and co-localization experiments, EK01 showed excellent cell membrane permeability and low cytotoxicity against MCF-10A (human mammary epithelial cell line) and HT-29 (human colorectal adenocarcinoma cell line). Particularly, we surprisingly discovered that EK01 could selectively aggregate in mitochondria and specific stain it in a green emissive fluorescent form, which means that EK01 could be a real-time specifically monitor of mitochondria in living cells with a high signal-to-noise ratio. Hence a new mitochondria imaging method was established which is incubating EK01 with living cells for 1 h at a final concentration of 6–12 μM, then visualizing under a confocal microscope at 395 nm. It is worth noting that the fluorescence efficiency of EK01 is not outstanding in organisms, it has much stronger fluorescence efficiency in other organic solvent systems (such as DMF, acetone and CH2Cl2). Therefore, as a new type of fluorescent core that is easy to synthesis and graft, we believe that (E)-2-styrylanthracene-9,10-diones have the potential to develop a variety of fluorescence platforms applying in different fields.
Green synthesis method for preparing 2-alkylanthraquinone from phthalic anhydride in one step
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Paragraph 0034-0035; 0042-0045, (2020/06/16)
The invention relates to the technical field of green synthesis of organic matters. The invention relates to a synthetic method, in particular to a green synthetic method for preparing 2-alkylanthraquinone from phthalic anhydride in one step. According to the method, phthalic anhydride and alkylbenzene are used as raw materials, difunctional sulfonic acid type solid acid based on an HZSM-5 molecular sieve is used as a catalyst, phthalic anhydride and alkylbenzene are catalyzed to be subjected to a Friedel-Crafts acylation reaction and a dehydration cyclization reaction at the same time under the action of the catalyst, so that the 2-alkyl anthraquinone is prepared in one step, wherein the bifunctional sulfonic acid type solid acid based on the HZSM-5 molecular sieve is a sulfonic acid typeHZSM-5 molecular sieve obtained by carrying out sulfonation treatment on the HZSM-5 molecular sieve. According to the synthesis method of the 2-alkyl anthraquinone, the bifunctional (with strong Bronsted acidity and Lewis acidity) sulfonic acid type solid acid based on the HZSM-5 molecular sieve is used as the catalyst to replace AlCl3 and fuming sulfuric acid, so that generation of a large amount of waste residues, waste gas and wastewater is avoided, and green production is realized.
