dimethyl 2,5-bis[2'-(4'-hexylthienyl)]-1,4-benzenedicarboxylate | 947188-87-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl 2,5-bis[2'-(4'-hexylthienyl)]-1,4-benzenedicarboxylate
• 英文别名: Dimethyl 2,5-bis(4-hexylthiophen-2-yl)benzene-1,4-dicarboxylate
• CAS: 947188-87-6
• 化学式: C₃₀H₃₈O₄S₂
• 分子量: 526.761
• InChiKey: CXRJVLCIEYAPOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  36
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 2,5-bis[2'-(4'-hexylthienyl)]-1,4-benzenedicarboxylate 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 三氯化铝 、 草酰氯 、 水 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2,7-dibromo-3,8-dihexyl-4,9-dihydro-s-indaceno[1,2-b:5,6-b']dithiophene-4,9-dione
  参考文献：
  名称：

  Derivatives of 4,9-Dihydro-s-indaceno[1,2-b:5,6-b‘]dithiophene-4,9-dione:  Synthesis and Properties

  摘要：

  A new family of organic semiconducting materials (1-4) integrating the structural components of thiophene and fluorene into a single molecular entity was synthesized and characterized. Optical and electrochemical properties of these previously unknown 4,9-dihydro-s-indaceno[1,2-b:5,6-b ']dithiophene-4,9-dione derivatives were studied in detail. These materials possess unique optical properties with the longest wavelength absorption maxima around 500-800 nm, which gradually reached a saturation limit with the total number of thiophene units approaching eight. They also display dramatic change in the redox properties with increasing conjugation chain lengths. A thin film of oligomer 3 prepared by a solution-casting method showed a well-ordered solid-state structure according to X-ray diffraction analysis.

  DOI：

  10.1021/jo0704311
• 作为产物：
  描述：

  dimethyl 2,5-bis[2'-(4'-hexyl-5'-trimethylsilylthienyl)]-1,4-benzenedicarboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以99%的产率得到dimethyl 2,5-bis[2'-(4'-hexylthienyl)]-1,4-benzenedicarboxylate
  参考文献：
  名称：

  Derivatives of 4,9-Dihydro-s-indaceno[1,2-b:5,6-b‘]dithiophene-4,9-dione:  Synthesis and Properties

  摘要：

  A new family of organic semiconducting materials (1-4) integrating the structural components of thiophene and fluorene into a single molecular entity was synthesized and characterized. Optical and electrochemical properties of these previously unknown 4,9-dihydro-s-indaceno[1,2-b:5,6-b ']dithiophene-4,9-dione derivatives were studied in detail. These materials possess unique optical properties with the longest wavelength absorption maxima around 500-800 nm, which gradually reached a saturation limit with the total number of thiophene units approaching eight. They also display dramatic change in the redox properties with increasing conjugation chain lengths. A thin film of oligomer 3 prepared by a solution-casting method showed a well-ordered solid-state structure according to X-ray diffraction analysis.

  DOI：

  10.1021/jo0704311

文献信息

• Derivatives of 4,9-Dihydro-<i>s</i>-indaceno[1,2-<i>b</i>:5,6-<i>b</i>‘]dithiophene-4,9-dione:  Synthesis and Properties
  作者：Chunchang Zhao、Yong Zhang、Man-Kit Ng

  DOI：10.1021/jo0704311

  日期：2007.8.1

  A new family of organic semiconducting materials (1-4) integrating the structural components of thiophene and fluorene into a single molecular entity was synthesized and characterized. Optical and electrochemical properties of these previously unknown 4,9-dihydro-s-indaceno[1,2-b:5,6-b ']dithiophene-4,9-dione derivatives were studied in detail. These materials possess unique optical properties with the longest wavelength absorption maxima around 500-800 nm, which gradually reached a saturation limit with the total number of thiophene units approaching eight. They also display dramatic change in the redox properties with increasing conjugation chain lengths. A thin film of oligomer 3 prepared by a solution-casting method showed a well-ordered solid-state structure according to X-ray diffraction analysis.