523-27-3Relevant articles and documents
Synthesis of new anthracene derivatives
Cakmak, Osman,Erenler, Ramazan,Tutar, Ahmet,Celik, Nuray
, p. 1795 - 1801 (2006)
An efficient synthesis is described for hexabromoanthracenes 3 and 4 by direct bromination of 9,10-dibromoanthrecene 2. Whereas base-induced elimination of hexabromide 3 with t-BuOK gave 2,3,9,10-tetrabromoanthracene 5, the reaction of hexabromide 4 with DBU afforded 1,3,9,10-tetrabromoanthracene 6 as the sole product. Tetrabromide 5 was also obtained by aromatization of 1,4-dinitroxy-2,3,9,10-tetrabromo-1,2,3,4-tetrahydroanthracene 17. Efficient and convenient synthetic routes are described for the preparation of dinotroxy 17, dimethoxy 23, and dihydroxides 18 and 19 with silver-induced substitution of hexabromides 3 and 4. The hydroxy compounds 19 and 18 were converted to diepoxide 20 and monoepoxide 21, respectively, with sodium methoxide. Base-promoted aromatization of dimethoxide 23 afforded dibromomonomethoxides 26 and 27. Bromoanthracenes and isomeric arene oxides constitute valuable precursors for the preparation of functionalized substituted anthracene derivatives that are difficult to prepare by other routes.
Polybrominated anthracenes: Selective synthesis of tetrabromoanthracenes as precursors for the corresponding tetracyanoanthracenes
Akar, Kiymet Berkil,?akmak, Osman
, p. 312 - 314 (2013)
Selective and efficient methods for the preparation of both 2,7,9,10-tetrabromoanthracene 11 and 2,6,9,10-tetrabromoanthracene 12 are described. Photobromination of 2,9,10-tribromoanthracene 8 resulted in the formation of only one stereoisomeric heptabromide 10. Whilst thermal aromatization of the trans,cis,trans-1,2,3,4,6,9,10-heptabromo-1,2,3,4- tetrahydroanthracene 10 gave mainly 2,6,9,10-tetrabromoanthracene 12, the pyridine-induced elimination yielded 2,7,9,10-tetrabromoanthracene 11 as the only final product. Tetrabromide 11 was transformed into 2,7,9,10- tetracyanoanthracene 14, by copper-assisted nucleophilic substitution reaction, as a potential photoconductive product.
Synthesis and characterization of 9,10-[di-p-(7-diethylamino- coumarin-3-yl) thiopheneyl]anthracene as fluorescent material
Luo, Qinglong,Zhang, Hui,Zhao, Yuling,Wang, Jun,Yu, Tianzhi
, p. 89 - 98 (2018)
A novel N-coumarin derivative, namely 9,10-[di-p-(7-diethylamino-coumarin-3-yl) thiopheneyl]anthracene ((CTh)2A), containing anthracene as the core and 3-thiophene N-coumarin as the substituent was synthesized, and its structure was confirmed by 1H NMR and IR spectroscopies. The optical, electrochemical and thermal properties were investigated. Thermogravimetric analysis and PL spectra reveal the high thermal and good photoluminescence characteristics. The coumarin derivative exhibits blue photoluminescence with high fluorescence quantum yield in solution (up to 40%). The results show that the derivative would serve as promising organic light-emitting diode luminescent material.
Bromodimethylsulfonium bromide: A brominating reagent for the conversion of anthracene into 9,10-dibromoanthracene
Zhang, Xin,Liu, Ju-Yan,Wang, Ying,Yue, Min-Min,Yuan, Bin
, p. 435 - 437 (2014)
Bromodimethylsulfonium bromide (BDMS) was used as an efficient brominating reagent for the synthesis of 9,10-dibromoanthracene in dichloromethane. The desired products were obtained in excellent yields.
Synthesis and photophysical processes of an anthracene derivative containing hole transfer groups
Diao, Haipeng,Feng, Liheng
, p. 294 - 297 (2011)
A novel luminescent compound 9,10-di-(N-carbazovinylene)anthracene (DCVA) was synthesized by Heck reaction of 9,10-dibromoanthracene and N-vinylcarbazole. The structure was characterized by MS, 1H NMR and Elemental analysis. The photoluminescent properties of DCVA have been carefully investigated by UV-vis absorption and fluorescence emission spectra. The results showed that the luminescent quantum yield of DCVA was 0.73 in THF and it emitted blue-light with the band gap of 3.60 eV estimated from the onset absorption. In addition, the light-emission of DCVA can be quenched by electron acceptor (dimethyl terephthalate), however, the fluorescent intensities of DCVA were slowly increased with the addition of electron donor (N,N-dimethylaniline). Furthermore, the molecular interactions of DCVA with fullerene (C60) and carbon nanotubes (CNTs) were also investigated, which indicated the organic luminescent compound can be used as new fluorescent probe.
Multi-fold Sonogashira coupling: A new and convenient approach to obtain tetraalkynyl anthracenes with tunable photophysical properties
Islam, Khadimul,Narjinari, Himani,Bisarya, Akshara,Kumar, Akshai
, p. 9692 - 9704 (2021/11/30)
For the first time, a direct single-step one-pot route to access nine new symmetric tetraalkynylated anthracenes via Pd(CH3CN)2Cl2/cataCXiumA catalyzed tetra-fold Sonogashira coupling is reported. Five of these tetraalkynylated anthracenes have been crystallographically characterized, with two of them exhibiting multiple interactions that significantly shorten the inter-planar distances in the solid-state structure. The rich photophysical properties exhibited by these molecules hold immense promise for future applications in sensors and optoelectronic devices. Two of the considered tetraalkynylated anthracenes comprising a D-π-A-π-D motif demonstrate solvatochromism and halochromism, with one of them showing a low bandgap of 1.79 eV. The remaining compounds demonstrate bandgaps in the range of 1.79-2.04 eV.
Stepwise mechanism for the bromination of arenes by a hypervalent iodine reagent
Arrieta, Ana,Cossío, Fernando P.,Granados, Albert,Shafir, Alexandr,Vallribera, Adelina
, p. 2142 - 2150 (2020/03/11)
A mild, metal-free bromination method of arenes has been developed using the combination of bis(trifluoroacetoxy)iodobencene and trimethylsilyl bromide. In situ-formed dibromo(phenyl)-λ3-iodane (PhIBr2) is proposed as the reactive intermediate. This methodology using PIFA/TMSBr has been applied with success to a great number of substrates (25 examples). The treatment of mono-substituted activated arenes led to para-brominated products (2u-z) in excellent 83-96% yields. Density functional theory calculations indicate a stepwise mechanism involving a double bromine addition followed by a type II dyotropic reaction with concomitant re-aromatization of the six-membered ring.
