2,6-Divinyl-9,10-anthraquinone | 131559-13-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,6-Divinyl-9,10-anthraquinone
• 英文别名: 2,6-diethenyl-9,10-anthraquinone；2,6-Bis(ethenyl)anthracene-9,10-dione
• CAS: 131559-13-2
• 化学式: C₁₈H₁₂O₂
• 分子量: 260.292
• InChiKey: ANNYTBKNWXAQCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 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

• 作为产物：
  描述：

  2,6-二羟基蒽醌 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 lithium chloride 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 2,6-Divinyl-9,10-anthraquinone
  参考文献：
  名称：

  钯催化三氟甲基苯磺酸与锡烷的偶联反应合成蒽醌衍生物。

  摘要：

  钯催化的羟基蒽醌三氟甲磺酸酯与锡烷的偶联可在中性条件下有效地取代羟基蒽醌。

  DOI：

  10.1016/s0040-4039(00)97839-0

文献信息

• Strong intramolecular electronic interactions in an anthraquinone bridged bis-ethenylphthalocyaninatozinc(ii) triad
  作者：Andreas Gouloumis、Purificación Vázquez、Tomás Torres、Sheng-Gao Liu、Luis Echegoyen

  DOI：10.1039/b009917c

  日期：——

  Two metallophthalocyanines bridged by ethenyl spacers to an anthraquinone moiety have been synthesized; both spectroscopic and electrochemical experiments have demonstrated strong intramolecular electronic interactions between the phthalocyanine donors and the anthraquinone acceptor unit.

  我们合成了两种金属酞菁，它们通过乙烯基间隔与蒽醌分子桥接；光谱和电化学实验都证明了酞菁供体与蒽醌受体单元之间强烈的分子内电子相互作用。
• 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.
• TAMAYO, NURIA;ECHAVARREN, ANTONIO M.;PAREDES, M. CARMEN;FARINA, FRANCISCO+, TETRAHEDRON LETT., 31,(1990) N6, C. 5189-5192
  作者：TAMAYO, NURIA、ECHAVARREN, ANTONIO M.、PAREDES, M. CARMEN、FARINA, FRANCISCO+

  DOI：——

  日期：——