dimethyl 2,5-bis[2'-(4',5'-dihexylthienyl)]-1,4-benzenedicarboxylate | 947188-85-4

• 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',5'-dihexylthienyl)]-1,4-benzenedicarboxylate
• 英文别名: Dimethyl 2,5-bis(4,5-dihexylthiophen-2-yl)benzene-1,4-dicarboxylate
• CAS: 947188-85-4
• 化学式: C₄₂H₆₂O₄S₂
• 分子量: 695.084
• InChiKey: DQUJJRVOXXBTGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.9
• 重原子数：
  48
• 可旋转键数：
  26
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 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',5'-dihexylthienyl)]-1,4-benzenedicarboxylate 在 sodium hydroxide 、 三氯化铝 、 草酰氯 、 水 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.33h， 生成 2,3,7,8-tetrahexyl-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：

  4,5-dihexyl-2-tributylstannylthiophene 、 dimethyl 2,5-diiodoterephthalate 在 bis-triphenylphosphine-palladium(II) chloride 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以52%的产率得到dimethyl 2,5-bis[2'-(4',5'-dihexylthienyl)]-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