523-27-3Relevant academic research and scientific papers
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.
Unexpected photooxidation of H-bonded tetracene
Liang, Zhixiong,Zhao, Wei,Wang, Shenglong,Tang, Qin,Lam, Sheung-Chuen,Miao, Qian
, p. 2007 - 2010 (2008)
In our attempts of tuning the molecular packing of tetracene with H-bonding, we found that tetracenediamide was much more vulnerable to photooxidation than tetracene in crystals despite their similar sensitivity to photooxidation In solution. Unexpectedly photooxidation of tetracenediamide in solution and in crystals show different regioselectivities. To explain the regioselectivity, a mechanism Involving H-bonding is proposed. This study Indicates that molecular packing in solid state can play an important role In solid-gas reactions.
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 of monodisperse oligocarbazoles-functionalized anthracenes with intense blue-emitting
Zhan, Yong,Cao, Kaiyu,Xue, Pengchong,Lu, Ran
, p. 594 - 599 (2013)
New well-defined monodisperse oligocarbazoles-functionalized anthracenes An-OCZn (n = 1, 2, 3) have been synthesized through Suzuki cross-coupling reaction of the brominated oligocarbazoles and 9,10-bis(4,4,5,5-tetramethyl-1,3, 2-dioxaborolan-2-yl)anthracene. They show good solubility in organic solvents, including dichloromethane, chloroform, toluene, ethyl acetate, and tetrahydrofuran. It should be noted that, in the case of An-OCZn, the formation of the excimer based on anthracene unit is suppressed completely due to the introduction of oligocarbazoles in 9,10-position of anthracene so that an intense blue-emitting has been afforded. In addition, the obtained An-OCZn exhibit good electrochemical and thermal stabilities. Thus, the oligocarbazoles-functionalized anthracenes can be a class of promising candidates for novel blue-emitting materials employed in OLEDs or related devices.
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.
Intramolecular hydrogen bond-enhanced electroluminescence performance of hybridized local and charge transfer (HLCT) excited-state blue-emissive materials
Li, Wan,Chasing, Pongsakorn,Benchaphanthawee, Wachara,Nalaoh, Phattananawee,Chawanpunyawat, Thanyarat,Kaiyasuan, Chokchai,Kungwan, Nawee,Namuangruk, Supawadee,Sudyoadsuk, Taweesak,Promarak, Vinich
, p. 497 - 507 (2021)
The hybridized local and charge transfer (HLCT) excited state is a successful strategy to produce both high external and internal quantum efficiencies. Based on the HLCT scheme, two isomeric donor-acceptor (D-A)-type excited-state intramolecular proton transfer (ESIPT) chromophores of o-hydroxyphenyl phenanthroimidazole (HPI)-based emissive molecules (mTAHPI and pTAHPI) and their OH-protected derivatives (pTAPI) were designed and explored for organic light-emitting diodes (OLEDs). The photophysical study and density functional theory (DFT) calculations revealed that all molecules possessed the HLCT excited-state characters without exhibiting ESIPT photophysical properties, whereas the nuclear magnetic resonance spectroscopy, single-crystal and physical property analyses discovered the existence of strong intramolecular H bonds and intermolecular interactions in both mTAHPI and pTAHPI. Consequently, their OLEDs displayed blue emissions with a narrow full width at half maximum (65-68 nm) and achieved excellent electroluminescence (EL) performance with a low turn-on voltage of 2.8 V. Particularly, pTAHPI-based devices showed the highest maximum external quantum effciency (EQE) of 8.13% with an ultra-high brightness of 18?100 cd m-2. The maximum singlet exciton utilization efficiency (ηs) of the device was estimated to be as high as 94%, which is among the best results of blue electroluminescence to our knowledge. This journal is
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.
Molecular Scissoring: Facile 3D to 2D Conversion of Lanthanide Metal Organic Frameworks Via Solvent Exfoliation
Quah, Hong Sheng,Ng, Li Ting,Donnadieu, Bruno,Tan, Geok Kheng,Vittal, Jagadese J.
, p. 10851 - 10854 (2016)
Five lanthanide MOFs with pcu topology have been exfoliated into nanoplatelets of two-dimensional structures via sonication in the dimethylacetamide solvent. These nanosheets are fluorescent under two-photon excitation dominated by the ligand, indicating energy upconversion ability.
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.
An improved procedure for the preparation of 9,10-dibromoanthracene
Jones,Atherton
, p. 1799 - 1802 (2001)
An improved procedure is described for the dibromination of anthracene, affording 9,10-dibromoanthracene with yields >95%.
