anthra[2,3-b:7,6-b′]difuran-5,11-dione | 1420881-96-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: anthra[2,3-b:7,6-b′]difuran-5,11-dione
• 英文别名: 6,16-Dioxapentacyclo[11.7.0.03,11.05,9.015,19]icosa-1(13),3(11),4,7,9,14,17,19-octaene-2,12-dione
• CAS: 1420881-96-4
• 化学式: C₁₈H₈O₄
• 分子量: 288.259
• InChiKey: BWCBVXIFYYZDSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  anthra[2,3-b:7,6-b′]difuran-5,11-dione 、 丙二腈 在 吡啶 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到2,2'-(anthra[2,3-b:7,6-b']difuran-5,11-diylidene)dimalononitrile
  参考文献：
  名称：

  Effect of water of crystallization on aggregation-induced emission in structurally similar crystals

  摘要：

  DOI：

  10.1016/j.tetlet.2019.05.040
• 作为产物：
  描述：

  2,6-二羟基蒽醌 在 吡啶 、 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 碘 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 92.5h， 生成 anthra[2,3-b:7,6-b′]difuran-5,11-dione
  参考文献：
  名称：

  Effect of water of crystallization on aggregation-induced emission in structurally similar crystals

  摘要：

  DOI：

  10.1016/j.tetlet.2019.05.040

文献信息

• Solution-Processed Optoelectronic Properties of Functionalized Anthradifuran
  作者：Motonori Watanabe、Wei-Teing Su、Yuan Jay Chang、Ting-Han Chao、Yuh-Sheng Wen、Tahsin J. Chow

  DOI：10.1002/asia.201200834

  日期：2013.1

  Layering up: The synthesis, physical properties, crystal structures, and optoelectronic properties of trialkylsilylethynylanthradifuran derivatives have been reported. Their high solubility enabled them to be processed through a solution phase for the fabrication of organic field‐effect transistors (OFETs) and photovoltaic devices.

  分层：已经报道了三烷基甲硅烷基thylanlanthradifuran衍生物的合成，物理性质，晶体结构和光电性质。它们的高溶解度使它们可以通过溶液阶段进行处理，以制造有机场效应晶体管（OFET）和光伏器件。
• AROMATIC COMPOUND AND METHOD FOR PRODUCING SAME
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2383273A1

  公开（公告）日：2011-11-02

  An aromatic compound represented by the following formula (1). [In the formula, ring A and ring B each represent a benzene ring, an aromatic fused ring composed of 2-4 rings, a heteroaromatic ring or a heterocyclic aromatic fused ring composed of 2-4 rings, R1a represents a group -CHR2a-CHR2bR2c, and R1b, R1c and R1d each represent hydrogen, aryl or a group -CHR2d-CHR2eR2f. This is with the proviso that at least 2 of R1b, R1c and R1d are not hydrogen. R2a, R2b and R2c each represent hydrogen, alkyl, aryl or a substituted silyl group, and R2a and R2b may be bonded together to form a ring. R2d, R2e and R2f each represent hydrogen, alkyl, aryl or a substituted silyl group, and R2d and R2e may be bonded together to form a ring.]

  下式(1)所代表的芳香族化合物。 [式中，环 A 和环 B 分别代表苯环、由 2-4 个环组成的芳香族聚合环、杂芳环或由 2-4 个环组成的杂环芳香族聚合环，R1a 代表基团-CHR2a-CHR2bR2c，R1b、R1c 和 R1d 分别代表氢、芳基或基团-CHR2d-CHR2eR2f。但 R1b、R1c 和 R1d 中至少有 2 个不是氢。R2a、R2b 和 R2c 分别代表氢、烷基、芳基或取代的硅烷基，R2a 和 R2b 可键合在一起形成一个环。R2d、R2e 和 R2f 各自代表氢、烷基、芳基或取代的硅烷基，且 R2d 和 R2e 可键合在一起形成一个环]。
• Synthesis and Investigation of the Effect of Substitution on the Structure, Physical Properties, and Electrochemical Properties of Anthracenodifuran Derivatives
  作者：Motonori Watanabe、Yasutaka Doi、Hidehisa Hagiwara、Aleksandar Tsekov Staykov、Shintaro Ida、Taisuke Matsumoto、Teruo Shinmyozu、Tatsumi Ishihara

  DOI：10.1021/acs.joc.5b01525

  日期：2015.9.18

  A series of syn/anti mixtures of anthradifuran (ADF) and substituent compounds were systematically synthesized, and the effect of substitution at the 5,11-positions on the neutral and radical states of ADF was investigated. All compounds were measured and analyzed by absorption and fluorescence spectroscopy, cyclic voltammetry, electrochemical absorption spectroscopy, and DFT calculations. The absorption spectra of 5,11-substituent compounds in their neutral state were red-shifted. In addition, the substituted compounds exhibited increased thermal stability with respect to the parent la because of elongation of the pi-conjugation and an increased steric hindrance effect due to the bulky ethynyl substituent groups. The cyclic voltammograms of all of the compounds exhibited irreversible reduction potentials and irreversible oxidation potentials, except in the case of (trimethylsilyl)-silylethynyl-substituted ADF. When the materials were subjected to oxidation/reduction potentials, the radical cation and anion species were generated. The absorption spectra of the radical-cation species of the compounds exhibited similar characteristics and similar absorption ranges (550-1400 nm), whereas the spectra of the radical anion species were blue-shifted (550-850 nm) compared than that of the parent 1a(center dot-) (550-1100 nm). The DFT computation results suggested that the radical states of lowest energy transitions occurred primarily from pi to pi(somo) or from pi(somo) to pi*.
• Effect of water of crystallization on aggregation-induced emission in structurally similar crystals
  作者：Naoto Hayashi、Naoki Okamoto、Masaya Onoue、Kensuke Yamamoto、Junro Yoshino

  DOI：10.1016/j.tetlet.2019.05.040

  日期：2019.6