1,5-diethynylanthraquinone | 78053-71-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,5-diethynylanthraquinone
• 英文别名: 1,5-diethynyl-9,10-anthraquinone；1,5-diethynylanthracene-9,10-dione
• CAS: 78053-71-1
• 化学式: C₁₈H₈O₂
• 分子量: 256.26
• InChiKey: XBSTXVYCGIBYGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [RuHCl(CO)(PPh₃)₃] 、 1,5-diethynylanthraquinone 、 三甲基膦 以 四氢呋喃 、 二氯甲烷 为溶剂， 以32%的产率得到1,5-bis(mer-trans-CH=CHRuCl(CO)(trimethylphosphane)3)-9,10-anthraquinone
  参考文献：
  名称：

  Synthesis, Characterization, and Electrochemical Properties of Diruthenium Complexes Bridged by Anthraquinones

  摘要：

  We have prepared four isomeric binuclear ruthenium complexes, in which two ruthenium units have been attached to the 1,4-(4a), 1,5- (4b), 1,8- (4c), or 2,6-positions (4d) of a central anthraquinone (Aq) moiety, leading to packed (4c) or extended (4a,b,d) topologies. All of these bimetallic complexes were fully characterized by elemental analysis, H-1, C-13{H-1}, and P-31 NMR{H-1} spectrometry, and UV/vis spectrophotometry. Moreover, the structures of 4a,b were established by X-ray crystallography. The electrochemical properties of the stable binuclear ruthenium complexes 4a-d were investigated, revealing that the two metal centers in 4a-c could interact with each other through an anthraquinone bridge, suggesting that the electron-withdrawing carbonyl chain actually functions as an effective bridge.

  DOI：

  10.1021/om100932u
• 作为产物：
  描述：

  1,5-bis(ethynyl)anthracene 在 chromium(VI) oxide 、 溶剂黄146 作用下， 反应 0.67h， 以62%的产率得到1,5-diethynylanthraquinone
  参考文献：
  名称：

  Acetylenic derivatives of anthraquinone

  摘要：

  DOI：

  10.1007/bf00953587

文献信息

• Control Over Charge Separation in Phthalocyanine−Anthraquinone Conjugates as a Function of the Aggregation Status
  作者：Andreas Gouloumis、David González-Rodríguez、Purificación Vázquez、Tomás Torres、Shenggao Liu、Luis Echegoyen、Jeff Ramey、Gordon L. Hug、Dirk M. Guldi

  DOI：10.1021/ja055344+

  日期：2006.10.1

  We have prepared three isomeric donor-acceptor systems, in which two phthalocyanine (Pc) units have been attached to the 1-, 5- (1a), 1-, 8- (1b), or 2-, 6- (1c) positions of a central anthraquinone (AQ) moiety, leading to packed (1b) or extended (1a and 1c) topologies. The electronic interactions between the donor and the acceptor in the ground state or in the excited states have been studied by different electrochemical and photophysical techniques. Due to the markedly different topologies, we have been able to modify these interactions at the intramolecular level and, by a proper choice of the solvent environment, at the intermolecular level within aggregates. In triad 1b, the ZnPc units are forced to pi-stack cofacially and out of the plane of the AQ ring. Consequently, this molecule shows strong inter-Pc interactions that give rise to intramolecular excitonic coupling but a relatively small electronic communication with the AQ acceptor through the vinyl spacers. On the contrary, the 1-, 5- or 2-, 6- connections of triads 1a and 1c allow for an efficient pi-conjugation between the active units that extends over the entire planar system. These two molecules tend to aggregate in aromatic solvents by pi-pi stacking, giving rise to J-type oligomers. Photoexcitation of the Pc units of 1a-c results in the formation of the Pc center dot+-AQ(center dot-) charge transfer state. We have demonstrated that the kinetics of these electron transfer reactions is greatly dependent on the aggregation status of the triads.
• MOROZ A. A.; PISKUNOV A. V.; SHVARTSBERG M. S., IZV. AN CCCP. CEP. XIM., 1981, HO 2, 386-390
  作者：MOROZ A. A.、 PISKUNOV A. V.、 SHVARTSBERG M. S.

  DOI：——

  日期：——