4,5-Didodecoxy-2,7-dithiophen-2-ylthieno[3,2-e][1]benzothiole | 1487423-79-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 4,5-Didodecoxy-2,7-dithiophen-2-ylthieno[3,2-e][1]benzothiole
• 英文别名: 4,5-didodecoxy-2,7-dithiophen-2-ylthieno[3,2-e][1]benzothiole
• CAS: 1487423-79-9
• 化学式: C₄₂H₅₈O₂S₄
• 分子量: 723.185
• InChiKey: DDXNFDZDHPVCEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.8
• 重原子数：
  48
• 可旋转键数：
  26
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5-Didodecoxy-2,7-dithiophen-2-ylthieno[3,2-e][1]benzothiole 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 20.0h， 以56%的产率得到7,8-didodecyloxybenzo[1,2-b:4,3-b’]dithiophene
  参考文献：
  名称：

  Benzodithiophene based π-conjugated macrocycles: synthesis, morphology and electrochemical characterization

  摘要：

  通过Ti(IV)介导的McMurry反应，从噻吩封端的BdT-Dod共聚单体合成了含有大环的7,8-二十二烷氧基苯并[1,2-b:4,3-b²]二噻吩（BdT-Dod），并通过1H NMR、13C NMR和MALDI-TOF质谱法对其进行了表征。此外，还通过AFM和SEM进行了形态学表征，以研究其自聚集特性。大环在固态下进行自组装，在Si/SiO2表面形成纤维，长度在μm范围内，厚度约为400 nm。

  DOI：

  10.1039/c4ob01043d
• 作为产物：
  描述：

  2-噻吩硼酸 、 2,7-Dibromo-4,5-didodecoxythieno[3,2-e][1]benzothiole 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium fluoride 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 20.0h， 以95%的产率得到4,5-Didodecoxy-2,7-dithiophen-2-ylthieno[3,2-e][1]benzothiole
  参考文献：
  名称：

  Benzodithiophene based π-conjugated macrocycles: synthesis, morphology and electrochemical characterization

  摘要：

  通过Ti(IV)介导的McMurry反应，从噻吩封端的BdT-Dod共聚单体合成了含有大环的7,8-二十二烷氧基苯并[1,2-b:4,3-b²]二噻吩（BdT-Dod），并通过1H NMR、13C NMR和MALDI-TOF质谱法对其进行了表征。此外，还通过AFM和SEM进行了形态学表征，以研究其自聚集特性。大环在固态下进行自组装，在Si/SiO2表面形成纤维，长度在μm范围内，厚度约为400 nm。

  DOI：

  10.1039/c4ob01043d

文献信息

• Electrochemical Route to Solution-Processable Polymers of Thiophene/Selenophene Capped Didodecyloxybenzo[1,2-<i>b</i>:4,3-<i>b</i>′]dithiophene and Their Optoelectronic Properties
  作者：Anjan Bedi、Sanjio S. Zade

  DOI：10.1021/ma401853q

  日期：2013.11.26

  Two new solution-processable polymers P1 and P2 are being reported here, which were prepared by electrochemical polymerization of thiophene and selenophene capped 7,8-didodecyloxybenzo[1,2-b:4,3-b']dithiophene (BdT-Dod), respectively and characterized by gel permeation chromatography (GPC) and H-1 NMR. The selenophene containing polymer possesses lower band gap than the thiophene analogue. Density functional theory (DFT) calculation showed the highly curved structure of the polymers and reproduced the trend in their optical band gaps. P2 showed larger bathochromic shift in the absorption spectrum from solution to film state compared to that of P1, which indicates better pi-stacking interaction in the solid state for P2. In spite of having highly curved chains, the polymers successfully exhibited electrochromic switching. The exchange of the end-caps from thiophene to selenophene have manifested with higher electrochromic switching ability and better polaronic and bipolaronic features in spectroelectrochemical measurement of P2 than that of P1. Kinetic study on the polymer films using chronoamperometry revealed that the selenophene containing polymer P2 afforded triangle%T similar to 60 in the visible region with a coloration efficiency of 100 cm(2) C-1. Electrochemical polymerization of BdT-Dod using different solvent/electrolyte systems was unsuccessful.
• Benzodithiophene based π-conjugated macrocycles: synthesis, morphology and electrochemical characterization
  作者：Anjan Bedi、Sanjio S. Zade

  DOI：10.1039/c4ob01043d

  日期：——

  A 7,8-didodecyloxybenzo[1,2-b:4,3-b′]dithiophene (BdT-Dod) containing a macrocycle was synthesized from a thiophene capped BdT-Dod comonomer through a Ti(IV) mediated McMurry reaction and characterized by 1H NMR, 13C NMR and MALDI-TOF mass spectrometry. Additionally, the morphological characterization was performed by AFM and SEM to investigate the self-aggregation properties. The macrocycle underwent self-assembly in the solid state to form fibers on the Si/SiO2 surface with a length in the μm range and a thickness of about 400 nm.

  通过Ti(IV)介导的McMurry反应，从噻吩封端的BdT-Dod共聚单体合成了含有大环的7,8-二十二烷氧基苯并[1,2-b:4,3-b²]二噻吩（BdT-Dod），并通过1H NMR、13C NMR和MALDI-TOF质谱法对其进行了表征。此外，还通过AFM和SEM进行了形态学表征，以研究其自聚集特性。大环在固态下进行自组装，在Si/SiO2表面形成纤维，长度在μm范围内，厚度约为400 nm。