2-(Dodecyloxy)-6-((5-(thiophen-3-yl)pentyl)oxy)anthracene-9,10-dione | 540475-27-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(Dodecyloxy)-6-((5-(thiophen-3-yl)pentyl)oxy)anthracene-9,10-dione
• 英文别名: 2-dodecoxy-6-(5-thiophen-3-ylpentoxy)anthracene-9,10-dione
• CAS: 540475-27-2
• 化学式: C₃₅H₄₄O₄S
• 分子量: 560.798
• InChiKey: VKMQIDAYJWGEBB-UHFFFAOYSA-N

物化性质

• 沸点：
  692.3±55.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  40
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  丙二腈 、 2-(Dodecyloxy)-6-((5-(thiophen-3-yl)pentyl)oxy)anthracene-9,10-dione 在 吡啶 、 四氯化钛 作用下， 以 氯仿 为溶剂， 反应 72.0h， 以84%的产率得到2-[10-(Dicyanomethylidene)-6-dodecoxy-2-(5-thiophen-3-ylpentoxy)anthracen-9-ylidene]propanedinitrile
  参考文献：
  名称：

  Synthesis of Soluble Donor−Acceptor Double-Cable Polymers Based on Polythiophene and Tetracyanoanthraquinodimethane (TCAQ)

  摘要：

  [GRAPHICS]Novel suitably functionalized tetracyanoanthraquinodimethane (TCAQ) derivatives covalently linked to thiophene moieties have been synthesized. The thiophene-based monomers have been chemically polymerized and copolymerized to yield new and soluble donor-acceptor double-cable polymers. The absorption and emission data reveal that the optical properties can be finely tuned by modifying the ratio of monomers in the copolymerization process.

  DOI：

  10.1021/ol034324e
• 作为产物：
  描述：

  2,6-二羟基蒽醌 在 potassium carbonate 、 sodium iodide 作用下， 以 丙酮 为溶剂， 生成 2-(Dodecyloxy)-6-((5-(thiophen-3-yl)pentyl)oxy)anthracene-9,10-dione
  参考文献：
  名称：

  Donor–acceptor polythiophene copolymers with tunable acceptor content for photoelectric conversion devices

  摘要：

  报告了一系列新的取代聚噻吩的合成与表征，这些聚合物的侧链含有电子受体蒽醌部分。通过不同比例共同聚合烷基噻吩和含有蒽醌单体的噻吩，改变了受体的摩尔含量。NMR分析显示聚合初期单体投料组成和实际骨架单位组成之间存在良好的相关性。通过尺寸排斥色谱研究了共聚物的共轭长度和化学组成对分子量的依赖性。小角X射线散射和紫外-可见吸收光谱被用来监测固态中的有序程度和链组织。材料呈现层状组织，其中相邻侧链的蒽醌单元在一定程度上也以平行于聚噻吩主链的层状结构组织。溶液中的光致发光测量表明，在对聚噻吩主链进行光激发后，蒽醌部分作为电子受体，而共轭主链则作为电子供体。供体-受体比率的可调性以及固态中的形态使得这些光活性共聚物成为有机光电转换设备的有趣候选材料。

  DOI：

  10.1039/b311370a

文献信息

• Synthesis of Soluble Donor−Acceptor Double-Cable Polymers Based on Polythiophene and Tetracyanoanthraquinodimethane (TCAQ)
  作者：Francesco Giacalone、José L. Segura、Nazario Martín、Marinella Catellani、Silvia Luzzati、Natalia Lupsac

  DOI：10.1021/ol034324e

  日期：2003.5.1

  [GRAPHICS]Novel suitably functionalized tetracyanoanthraquinodimethane (TCAQ) derivatives covalently linked to thiophene moieties have been synthesized. The thiophene-based monomers have been chemically polymerized and copolymerized to yield new and soluble donor-acceptor double-cable polymers. The absorption and emission data reveal that the optical properties can be finely tuned by modifying the ratio of monomers in the copolymerization process.
• Donor–acceptor polythiophene copolymers with tunable acceptor content for photoelectric conversion devices
  作者：Marinella Catellani、Silvia Luzzati、Natalia-O. Lupsac、Raniero Mendichi、Roberto Consonni、Antonino Famulari、Stefano Valdo Meille、Francesco Giacalone、José L. Segura、Nazario Martín

  DOI：10.1039/b311370a

  日期：——

  The synthesis and characterization of a new series of substituted polythiophenes containing an electron acceptor anthraquinone moiety in the side chain are reported. The acceptor molar content was varied by the co-polymerization of both alkylthiophene and thiophene bearing anthraquinone monomers in different ratios. NMR analysis shows a good correlation between the monomer feed composition at the beginning of the polymerization and the actual unit composition of the backbone. The conjugation length and the chemical composition of the copolymers as a function of the molecular weight have been studied by size exclusion chromatography. Small angle X-ray scattering and UV-Vis absorption spectra have been used to monitor the degree of order and chain organization in the solid state. The materials exhibit a lamellar organization, in which the anthraquinone units of neighboring side chains are also organized to some degree in layered structures parallel to the polythiophene main chains. The photoluminescence measurements in solution suggest that, upon photoexcitation of the polythiophene backbone, the anthraquinone moieties act as electron acceptors and the conjugated backbone as electron donor. The tunability of the donor–acceptor ratio and the morphology in the solid state make these photoactive copolymers interesting candidates for organic photoelectric conversion devices.

  报告了一系列新的取代聚噻吩的合成与表征，这些聚合物的侧链含有电子受体蒽醌部分。通过不同比例共同聚合烷基噻吩和含有蒽醌单体的噻吩，改变了受体的摩尔含量。NMR分析显示聚合初期单体投料组成和实际骨架单位组成之间存在良好的相关性。通过尺寸排斥色谱研究了共聚物的共轭长度和化学组成对分子量的依赖性。小角X射线散射和紫外-可见吸收光谱被用来监测固态中的有序程度和链组织。材料呈现层状组织，其中相邻侧链的蒽醌单元在一定程度上也以平行于聚噻吩主链的层状结构组织。溶液中的光致发光测量表明，在对聚噻吩主链进行光激发后，蒽醌部分作为电子受体，而共轭主链则作为电子供体。供体-受体比率的可调性以及固态中的形态使得这些光活性共聚物成为有机光电转换设备的有趣候选材料。