1,3-bis(5-ethynyl-2-thienyl)benzo[c]thiophene | 1447604-52-5

• 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: 1,3-bis(5-ethynyl-2-thienyl)benzo[c]thiophene
• 英文别名: 1,3-Bis(5-ethynylthiophen-2-yl)-2-benzothiophene；1,3-bis(5-ethynylthiophen-2-yl)-2-benzothiophene
• CAS: 1447604-52-5
• 化学式: C₂₀H₁₀S₃
• 分子量: 346.497
• InChiKey: OAQKOWUOQJWCSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-bis(5-ethynyl-2-thienyl)benzo[c]thiophene 、 足球烯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 氯苯 为溶剂， 以18%的产率得到1,3-bis(5-ethynyl-2-thienyl)benzo[c]thiophene-di(hydrofullerene)
  参考文献：
  名称：

  Synthesis and Photophysical Properties of Some Dithienylbenzo[c]thiophene Derivatives

  摘要：

  The synthesis of a new fullerene - dithienylbenzo[c]thiophene (DTBT) - fullerene triad has been reported. The synthetic scheme provides the synthesis of DTBT unit, a Sonogashira reaction to introduce two acetylenic groups and the coupling with fullerene. The product showed an absorption at 485 rim and a fluorescence band at 575 nm. Treatment of 5-(3-(5-ethynyl-2-thienyl)benzo[c]-1-thienyl)thiophene-2-carbaldehyde with LHDMS gave a dimeric product that showed an absorption at 475 nm and a fluorescence band at 595 nm. Furthermore, 5-(3-(2-thienyl)benzo[c]-1-thienyl)thiophene-2-carbaldehyde was treated with hydrazine to give the corresponding adduct that showed an absorption at 480 nm and a fluorescence band at 605 rim.

  DOI：

  10.3987/com-14-13145
• 作为产物：
  描述：

  1,3-bis-(5-bromothiophen-2-yl)benzo[c]thiophene 在 哌啶 、 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 2.5h， 生成 1,3-bis(5-ethynyl-2-thienyl)benzo[c]thiophene
  参考文献：
  名称：

  Synthesis and Photophysical Properties of Some Dithienylbenzo[c]thiophene Derivatives

  摘要：

  The synthesis of a new fullerene - dithienylbenzo[c]thiophene (DTBT) - fullerene triad has been reported. The synthetic scheme provides the synthesis of DTBT unit, a Sonogashira reaction to introduce two acetylenic groups and the coupling with fullerene. The product showed an absorption at 485 rim and a fluorescence band at 575 nm. Treatment of 5-(3-(5-ethynyl-2-thienyl)benzo[c]-1-thienyl)thiophene-2-carbaldehyde with LHDMS gave a dimeric product that showed an absorption at 475 nm and a fluorescence band at 595 nm. Furthermore, 5-(3-(2-thienyl)benzo[c]-1-thienyl)thiophene-2-carbaldehyde was treated with hydrazine to give the corresponding adduct that showed an absorption at 480 nm and a fluorescence band at 605 rim.

  DOI：

  10.3987/com-14-13145

文献信息

• Synthetic Approach to and Characterization of a Fullerene-DTBT-Fullerene Triad
  作者：Maurizio D'Auria、Ambra Guarnaccio、Rocco Racioppi、Antonio Santagata、Roberto Teghil

  DOI：10.1055/s-0032-1316902

  日期：——

  The synthesis of a new fullerene-dithienylbenzo[c]thiophene (DTBT)-fullerene triad is reported. The synthetic approach involves the synthesis of a DTBT unit, a Sonogashira reaction to introduce two acetylenic groups, and the coupling with fullerene. The product showed an absorption at lambda = 485 nm and a fluorescence band at lambda = 575 nm.
• Synthesis and Photophysical Properties of Some Dithienylbenzo[c]thiophene Derivatives
  作者：Maurizio D'Auria、Ambra Guarnaccio、Rocco Racioppi、Antonio Santagata、Roberto Teghil

  DOI：10.3987/com-14-13145

  日期：——

  The synthesis of a new fullerene - dithienylbenzo[c]thiophene (DTBT) - fullerene triad has been reported. The synthetic scheme provides the synthesis of DTBT unit, a Sonogashira reaction to introduce two acetylenic groups and the coupling with fullerene. The product showed an absorption at 485 rim and a fluorescence band at 575 nm. Treatment of 5-(3-(5-ethynyl-2-thienyl)benzo[c]-1-thienyl)thiophene-2-carbaldehyde with LHDMS gave a dimeric product that showed an absorption at 475 nm and a fluorescence band at 595 nm. Furthermore, 5-(3-(2-thienyl)benzo[c]-1-thienyl)thiophene-2-carbaldehyde was treated with hydrazine to give the corresponding adduct that showed an absorption at 480 nm and a fluorescence band at 605 rim.