2,7-bis[2'-(5-bromothienyl)]-3,8-dihexyl-4,9-dihydro-s-indaceno[1,2-b:5,6-b']dithiophene-4,9-dione | 947188-98-9

• 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: 2,7-bis[2'-(5-bromothienyl)]-3,8-dihexyl-4,9-dihydro-s-indaceno[1,2-b:5,6-b']dithiophene-4,9-dione
• 英文别名: 6,15-Bis(5-bromothiophen-2-yl)-7,16-dihexyl-5,14-dithiapentacyclo[10.6.0.03,10.04,8.013,17]octadeca-1(12),2,4(8),6,10,13(17),15-heptaene-9,18-dione
• CAS: 947188-98-9
• 化学式: C₃₆H₃₂Br₂O₂S₄
• 分子量: 784.721
• InChiKey: JQAPIRDAZSBOAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.4
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  147
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,7-bis[2'-(5-bromothienyl)]-3,8-dihexyl-4,9-dihydro-s-indaceno[1,2-b:5,6-b']dithiophene-4,9-dione 、 (5'-己基-[2,2'-联噻吩]-5-基)三丁基锡 在 bis-triphenylphosphine-palladium(II) chloride 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 36.0h， 以50%的产率得到2,7-bis[2'-(5'''-hexyl-5',2'';5'',2'''-terthienyl)]-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 bis-triphenylphosphine-palladium(II) chloride sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 三氯化铝 、 草酰氯 、 水 、 溶剂黄146 、 三苯基膦 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 49.0h， 生成 2,7-bis[2'-(5-bromothienyl)]-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

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.