3,3-dihexyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine | 700816-98-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3-dihexyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine
• 英文别名: 2H-Thieno[3,4-b][1,4]dioxepin, 3,3-dihexyl-3,4-dihydro-；3,3-dihexyl-2,4-dihydrothieno[3,4-b][1,4]dioxepine
• CAS: 700816-98-4
• 化学式: C₁₉H₃₂O₂S
• 分子量: 324.528
• InChiKey: NZMMQKZBBGHOQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,3-dihexyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 3.0h， 生成 (2Z,2'Z)-2,2'-[2,5-bis(dodecyloxy)-1,4-phenylene]bis[3-(3,3-dihexyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepin-6-yl)acrylonitrile]
  参考文献：
  名称：

  Soluble Narrow Band Gap and Blue Propylenedioxythiophene-Cyanovinylene Polymers as Multifunctional Materials for Photovoltaic and Electrochromic Applications

  摘要：

  A family of soluble narrow band gap donor- acceptor conjugated polymers based on dioxythiophenes and cyanovinylenes is reported. The polymers were synthesized using Knoevenagel polycondensation or Yamamoto coupling polymerizations to yield polymers with molecular weights on the order of 10000-20000 g/mol, which possess solubility in common organic solvents. Thin film optical measurements revealed narrow band gaps of 1.5-1.8 eV, which gives the polymers a strong overlap of the solar spectrum. The energetic positions of the band edges were determined by cyclic voltammetry and differential pulse voltammetry and demonstrate that the polymers are both air stable and show a strong propensity for photoinduced charge transfer to fullerene acceptors. Such measurements also suggest that the polymers can be both p- and n-type doped, which is supported by spectroelectrochemical results. These polymers have been investigated as electron donors in photovoltaic devices in combination with PCBM ([6,6]-phenyl C-61-butyric acid methyl ester) as an electron acceptor based on the near ideal band structures designed into the polymers. Efficiencies as high as 0.2% (AM1.5) with short circuit current densities as high as 1.2-1.3 mA/cm(2) have been observed in polymer/PCBM (1: 4 by weight) devices and external quantum efficiencies of more than 10% have been observed at wavelengths longer than 600 nm. The electrochromic properties of the narrow band gap polymers are also of interest as the polymers show three accessible color states changing from an absorptive blue or purple in the neutral state to a transmissive sky-blue or gray in the oxidized and reduced forms. The wide electrochemical range of electrochromic activity coupled with the strong observed changes in transmissivity between oxidation states makes these materials potentially interesting for application to electrochromic displays.

  DOI：

  10.1021/ja061274a
• 作为产物：
  描述：

  dimethyl dihexylmalonate 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 336.0h， 生成 3,3-dihexyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine
  参考文献：
  名称：

  区域对称的3,4-二氧基官能化聚噻吩的结构-性质关系

  摘要：

  我们提出了合成和表征含有单和二烷基化的3,4-亚丙基二氧噻吩的新型均聚物和共聚物，目的是创建在聚合物电子学和光子学领域中要开发的新型π-共轭聚合物。我们表明，大的七元二氧杂环丁烷环连接到噻吩部分会导致不利的空间相互作用，尤其是在均聚物中；因此，它防止了聚合物在固态下以短的π堆积距离适应共面结构。我们进一步表明，将较少量的未取代噻吩单元形式的空间填充单元掺入到聚合物链中减少了这些不利的相互作用，因此允许在固态下更共面的聚合物主链取向和更短的π堆积距离。

  DOI：

  10.1021/ma051609t

文献信息

• Amplified Fluorescence Polymers and Sensor Thereof
  申请人：Kumar Anil

  公开号：US20110207114A1

  公开（公告）日：2011-08-25

  The present disclosure is related to amplified fluorescence polymers (AFPs) with pendant functional groups, their derivatives and their synthesis. The amplified fluorescence polymers can be used in various biological and chemical sensors.

  本公开涉及带有侧链官能团的增强荧光聚合物（AFPs），它们的衍生物以及它们的合成。这些增强荧光聚合物可以用于各种生物和化学传感器中。
• Structural, Optical, and Electronic Properties of a Series of 3,4-Propylenedioxythiophene Oligomers in Neutral and Various Oxidation States
  作者：Chuanwen Lin、Takanori Endo、Masayoshi Takase、Masahiko Iyoda、Tohru Nishinaga

  DOI：10.1021/ja2035442

  日期：2011.7.27

  (ProDOT) oligomers (nP(Hex)) with dihexyl side chains and methylthio end-capping units was synthesized as a model of poly(3,4-alkylenedioxythiophene)s. The slope of the linear relationship between the energy of the absorption maxima of nP(Hex) in the neutral states and the reciprocal of the number of monomer units (1/n) was found to be comparable to that of 3,4-ethylenedioxythiophene (EDOT) oligomers, suggesting

  合成了一系列具有二己基侧链和甲硫基封端单元的 3,4-丙烯二氧噻吩 (ProDOT) 低聚物 (nP(Hex)) 作为聚 (3,4-亚烷基二氧噻吩) 的模型。发现在中性状态下 nP(Hex) 的吸收最大值的能量与单体单元数的倒数 (1/n) 之间的线性关系的斜率与 3,4-亚乙基二氧噻吩的相当。 EDOT) 低聚物，表明 ProDOT 和 EDOT 低聚物具有相似的有效结合。在循环伏安法测量中，第一和第二氧化波以及第三和第四波都显示出随着链长度的增加而合并成一个峰。nP(Hex) 与 SbCl(5) 在室温下在 CH(2)Cl(2) 中的逐步化学氧化得到稳定的各种氧化态的阳离子物质，并且发现只有自由基阳离子（极化子）具有可见光区有明显的吸收带。有趣的是，当在低温下测量四聚体自由基阳离子 4P(Hex)(+·) 的吸收光谱时，除了 π- 外，还观察到可逆歧化为 dication 4P(Hex)(2+)
• Theoretical and experimental investigation of bridging atom effect on the fluorene and silafluorene based trimeric monomers and their corresponding polymers
  作者：Elif Demir Arabacı、Erol Yildirim、Ahmet M. Önal

  DOI：10.1016/j.dyepig.2023.111320

  日期：2023.8

  A series of monomers bearing fluorene and silafluorene with different bridging atoms and 3,4-ethylenedioxythiophene (EDOT) and 3,4-propylenedioxythiophene (ProDOT) as the donor units were synthesized via Stille coupling. To investigate the effect of different donor units and different bridging atoms, the optical and electrochemical behaviors of the monomers and their corresponding polymers were investigated

  通过 Stille 偶联合成了一系列带有不同桥原子的芴和硅氟烯的单体，以 3,4-亚乙基二氧噻吩 (EDOT) 和 3,4-亚丙基二氧噻吩 (ProDOT) 作为供体单元。为了研究不同供体单元和不同桥接原子的影响，通过一些电分析和光谱技术研究了单体及其相应聚合物的光学和电化学行为。单体的电聚合通过重复循环以动电位方式进行。电化学研究表明，发现含硅氟烯的单体及其相应的聚合物表现出略低的氧化电位和较低的带隙（E g) 与其含芴类似物相比的值。此外，两个不同供体组之间的比较表明，与带有 ProDOT 单元的聚合物相比，带有 EDOT 单元的聚合物的 E g较低（约 0.30 eV），这是由于 ProDOT 的扭曲结构减少了氧原子之间的重叠对和芳香族噻吩环。DFT计算进一步证实了该结果。
• Ionic and electronic conducting binder for electrochemical devices
  申请人：Nissan North America, Inc.

  公开号：US10377849B2

  公开（公告）日：2019-08-13

  An ion conducting and electron conducting polymer is comprised of a first polymer of a single-sulfonic acid polymer or a multi-sulfonic acid polymer and a second polymer of an EDOT analog monomer having the following formula: wherein z=O or S; Y2=—COH, —C6H13, or —COOH; a=0 or 1; Y3=—CH3, —C2H5, —CH2C6H6, —C6H13, —C8H17, —CH2OC6H13, or —CH2OC6H6; and b=0 or 1; wherein a sulfonic acid group of each branch of the first polymer electronically interacts with one or more thiophene rings of the second polymer; and wherein any remaining sulfonic acid groups on each branch of the first polymer are converted to SO3Li.

  离子导电和电子导电聚合物是由单磺酸聚合物或多磺酸聚合物的第一种聚合物和 EDOT 类似单体的第二种聚合物组成，EDOT 类似单体的分子式如下： 其中 z=O 或 S； Y2=-COH、-C6H13 或 -COOH；a=0 或 1；Y3=-CH3、-C2H5、-CH2C6H6、-C6H13、-C8H17、-CH2OC6H13 或 -CH2OC6H6；以及 b=0 或 1；其中，第一种聚合物的每个支链的磺酸基团与第二种聚合物的一个或多个噻吩环发生电子相互作用；第一种聚合物的每个支链上的任何剩余磺酸基团转化为 SO3Li。
• Spectral Broadening in MEH-PPV:PCBM-Based Photovoltaic Devices via Blending with a Narrow Band Gap Cyanovinylene−Dioxythiophene Polymer
  作者：Barry C. Thompson、Young-Gi Kim、John R. Reynolds

  DOI：10.1021/ma0505934

  日期：2005.6.1