9,10-anthraquinone-2,3-dicarboxylic anhydride | 6705-73-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-anthraquinone-2,3-dicarboxylic anhydride
• 英文别名: anthraquinone-2,3-dicarboxylic anhydride；9,10-dioxo-9,10-dihydro-anthracene-2,3-dicarboxylic acid-anhydride；9,10-Dioxo-9,10-dihydro-anthracen-2,3-dicarbonsaeure-anhydrid；naphtho[2,3-f][2]benzofuran-1,3,5,10-tetrone
• CAS: 6705-73-3
• 化学式: C₁₆H₆O₅
• 分子量: 278.221
• InChiKey: RUXFMPOMADVYPH-UHFFFAOYSA-N

物化性质

• 沸点：
  560.7±39.0 °C(Predicted)
• 密度：
  1.615±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9,10-anthraquinone-2,3-dicarboxylic anhydride 在 ammonium hydroxide 作用下， 生成 3-carbamoyl-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid
  参考文献：
  名称：

  Photochemistry of anthrabarrelene. Mechanistic and exploratory organic photochemistry. LXXIX

  摘要：

  DOI：

  10.1021/ja00793a024
• 作为产物：
  描述：

  蒽醌-2,3-二甲酸 生成 9,10-anthraquinone-2,3-dicarboxylic anhydride
  参考文献：
  名称：

  Elbs, Journal fur praktische Chemie (Leipzig 1954), 1890, vol. <2> 41, p. 21

  摘要：

  DOI：

文献信息

• Isomer effect on the near-infrared electrochromism of anthraquinone imides
  作者：Bin Yao、Fengkun Chen、Hong Jiang、Jie Zhang、Xinhua Wan

  DOI：10.1016/j.electacta.2015.03.057

  日期：2015.6

  radical anions were greatly dependent on the structures of isomers. The radical anions of Ia, IIa, and IIb illustrated NIR absorptions peaked at 820, 1260, and 1380 nm, respectively, but that of Ib exhibited only weak absorption in the visible region centered at 660 nm. Gaussian calculations suggested that the electrons were delocalized over the whole molecular skeletons of Ia and IIa radical anions, but

  为了深入研究蒽醌酰亚胺的分子结构与近红外电致变色之间的相互作用，合成了蒽醌酰亚胺的两对未取代异构体（Ia和Ib）和硝基取代异构体（IIa和IIb），其中分子Ia和IIa比Ib和IIb具有更多的线性形状。结合循环伏安法和光谱电化学研究其电化学性质。循环伏安法显示Ib和IIb揭示与它们的异构体相比，首次还原电势降低且循环稳定性低，表明异构化削弱了稳定作用。在单电子还原时，自由基阴离子的吸收波长和吸收强度都极大地取决于异构体的结构。Ia，IIa和IIb的自由基阴离子显示NIR吸收分别在820、1260和1380 nm处达到峰值，但是Ib的阴离子仅在以660 nm为中心的可见区域中显示弱吸收。高斯计算表明，电子在Ia和IIa的整个分子骨架上都离域化了自由基阴离子，但有效结合长度在Ib和IIb的酰亚胺部分中断了。考虑了异构体对有效共轭长度和电子密度分布的影响，以合理化不同的电致变色行为。
• Synthesis and characterization of a novel kind of near-infrared electrochromic polymers containing an anthraquinone imide group and ionic moieties
  作者：Yijun Zheng、Jia Zheng、Letian Dou、Wenqiang Qiao、Xinhua Wan

  DOI：10.1039/b915978a

  日期：——

  A novel near-infrared (NIR) electrochromic polyelectrolyte consisting of anthraquinone imide (AQI) pendants and a poly(1-vinylimidazole bromide) main chain was synthesized viaradical polymerization. Its AQI content was varied by copolymerization with 1-vinyl-3-butylimidazole bromide to improve the processability of the polymer as well as the monomer conversion. The electrochemical and electrochromic properties of both homopolymer and copolymers were investigated. All the (co)polymers exhibited two reversible redox states (radical anions and dianions). Spectroelectrochemical analysis in solution showed that the radical anions possessed intense NIR absorptions with λmax values in the range 820 to 830 nm, while the dianions exhibited absorptions between 460 and 560 nm. The homopolymer film displayed an optical attenuation of 3 dB/µm at 810 nm with a switching time of 20 s. Such a polymer can change color in a single film device without any additional electrolytes and showed a rapid response time of 1 s at 810 nm.

  一种新型的近红外（NIR）电致变色聚电解质由蒽醌亚胺（AQI）垂丝和聚（1-乙烯基溴化咪唑）主链组成。通过与 1-乙烯基-3-丁基溴化咪唑共聚，改变了 AQI 的含量，从而提高了聚合物的加工性和单体转化率。研究了均聚物和共聚物的电化学和电致变色特性。所有（共）聚合物都呈现出两种可逆的氧化还原状态（自由基阴离子和二离子）。溶液中的光谱电化学分析表明，自由基阴离子具有强烈的近红外吸收，其 λmax 值在 820 至 830 纳米之间，而二元离子的吸收则在 460 至 560 纳米之间。均聚物薄膜在 810 纳米波长处的光衰减为 3 dB/µm，切换时间为 20 秒。这种聚合物可在单层薄膜装置中改变颜色，无需额外的电解质，在 810 纳米波长处的快速反应时间为 1 秒。
• Near-infrared electrochromic and chiroptical switching polymers: synthesis and characterization of helical poly(N-propargylamides) carrying anthraquinone imide moieties in side chains
  作者：Yijun Zheng、Jiaxi Cui、Jia Zheng、Xinhua Wan

  DOI：10.1039/b927360c

  日期：——

  Optically active poly(N-propargylamides) containing chiral anthraquinone imide (AQI) side groups have been synthesized. The chiroptical and electrochromic properties of the polymers are investigated. The polymers exhibit intense Cotton effects in the absorption regions of both main- and side-chains, strongly suggesting a helical conformation of the polymer backbone and a skewed packing of pendant chromophores. Additionally, the polymers show two reversible redox states (radical anion and dianion). Intense circular dichroism (CD) signals centered at 780 nm and 530 nm are assigned to the radical anion and dianion intermediates, respectively. The voltage-controlled reversible Cotton effects demonstrate the newly synthesized AQI-containing poly(N-propargylamides) as potential electrochemically driven chiroptical switching materials that operate in the near-infrared wavelength region.

  已合成了含有手性蒽醌亚胺（AQI）侧基的光学活性聚（N-丙炔酰胺）。研究了聚合物的旋光性和电致变色特性。聚合物在主链和侧链的吸收区域表现出强烈的棉花效应，这强烈表明聚合物主链呈螺旋构象，且侧基呈倾斜堆积。此外，聚合物还表现出两种可逆氧化还原状态（自由基阴离子和二阴离子）。强烈的圆二色性（CD）信号分别位于780 nm和530 nm，分别对应自由基阴离子和二阴离子中间体。电压可控的可逆棉花效应表明，新合成的含AQI的聚（N-丙炔酰胺）是潜在的电化学驱动的旋光性开关材料，可在近红外波长区域工作。
• Anthraquinone Photonuclease Structure Determines Its Mode of Binding to DNA and the Cleavage Chemistry Observed
  作者：David T. Breslin、Joseph E. Coury、Jaimie R. Anderson、Lori McFail-Isom、Yongzhi Kan、Loren Dean Williams、Lawrence A. Bottomley、Gary B. Schuster

  DOI：10.1021/ja963607h

  日期：1997.5.1

  by three general mechanisms: hydrolysis of the sugar phosphate bond,3 chemical modification of a DNA base,1a,b,4 or hydrogen abstraction from a deoxyribose unit.5 We recently described a set of anthraquinone derivatives that act as photonucleases.6

  分离功能性 DNA 序列 1 和开发成像（足迹）分子与 DNA 结合的试剂的愿望推动了切割 DNA 骨架的化学试剂的开发。 2 合成核酸酶是结构多样的化合物，通过三种一般机制起作用：糖磷酸键的水解、3 DNA 碱基的化学修饰、1a、b、4 或脱氧核糖单元的氢提取。 5 我们最近描述了一组作为光核酸酶的蒽醌衍生物。 6
• POLARIZING FILM
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0198082A1

  公开（公告）日：1986-10-22

  Polarizing film with excellent humidity and heat resistances, which is substantially insoluble in water, organic solvents, and liquid crystals and which comprises a hydrophobic polymer containing in an oriented state a dichroic organic dye having a dichroic ratio of 7 or more measured as a film formed by uniformly mixing the dye with polyethylene terephthalate and melt-forming the mixture into film.

  具有优异防潮和耐热性能的偏光膜，它基本上不溶于水、有机溶剂和液晶，由一种疏水性聚合物组成，该聚合物在定向状态下含有一种二色性有机染料，其二色性比率为 7 或更高，该薄膜是通过将该染料与聚对苯二甲酸乙二醇酯均匀混合并将混合物熔融成膜而形成的。