2-(4,5,6,7-tetrahydrobenzothien-2-yl)thiophene | 159633-42-8

• 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-(4,5,6,7-tetrahydrobenzothien-2-yl)thiophene
• 英文别名: 2-Thiophen-2-yl-4,5,6,7-tetrahydro-1-benzothiophene
• CAS: 159633-42-8
• 化学式: C₁₂H₁₂S₂
• 分子量: 220.359
• InChiKey: GJJHIQMXWJZYDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4,5,6,7-tetrahydrobenzothien-2-yl)thiophene 在 正丁基锂 、 草酰氯 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 5-(4,5,6,7-tetrahydrobenzothien-2-yl)thiophene-2-carbonic acid chloride
  参考文献：
  名称：

  Synthesis and Characterization of Mixed Oligoheterocycles Based on End-capped Oligothiophenes

  摘要：

  A homologous series of mixed oligoheterocycles 2-6, based on the end-capped quinquethiophene EC5T 1, was synthesized by the introduction of electronegative heteroatoms, such as oxygen and nitrogen, into the conjugated Jc-system. This led to novel structures in which the central thiophene unit of the parent compound 1 is substituted by other heterocycles (thiazole, 1,3,4-thiadiazole, furan, oxazole, Id,4-oxadiazole) that have a more pronounced acceptor character. The characterization of the optical and electrochemical properties clearly reveal the influence of the heteroatoms on the electronic properties. The electron-withdrawing character of the central heterocycles renders the oxidation of the oligomer more difficult while reduction is facilitated. Moreover, in some cases a hypsochromic shift of the longest-wavelength absorption and emission is observed along with a significant enhancement of the fluorescence quantum yield in solution and in the solid state. The HOMO/LUMO energy difference, determined from optical and electrochemical measurements, corresponds qualitatively well with the values obtained from semiempirical calculations. An X-ray structural determination was performed on oligoheterocycle 6 and the experimental and calculated data are compared.

  DOI：

  10.1002/(sici)1521-3765(19981102)4:11<2211::aid-chem2211>3.0.co;2-7
• 作为产物：
  描述：

  2-溴-1-(2-THIENYL)-1-ETHANONE 在 劳森试剂 、 水 作用下， 以 甲苯 为溶剂， 反应 10.0h， 生成 2-(4,5,6,7-tetrahydrobenzothien-2-yl)thiophene
  参考文献：
  名称：

  Synthesis and Characterization of Mixed Oligoheterocycles Based on End-capped Oligothiophenes

  摘要：

  A homologous series of mixed oligoheterocycles 2-6, based on the end-capped quinquethiophene EC5T 1, was synthesized by the introduction of electronegative heteroatoms, such as oxygen and nitrogen, into the conjugated Jc-system. This led to novel structures in which the central thiophene unit of the parent compound 1 is substituted by other heterocycles (thiazole, 1,3,4-thiadiazole, furan, oxazole, Id,4-oxadiazole) that have a more pronounced acceptor character. The characterization of the optical and electrochemical properties clearly reveal the influence of the heteroatoms on the electronic properties. The electron-withdrawing character of the central heterocycles renders the oxidation of the oligomer more difficult while reduction is facilitated. Moreover, in some cases a hypsochromic shift of the longest-wavelength absorption and emission is observed along with a significant enhancement of the fluorescence quantum yield in solution and in the solid state. The HOMO/LUMO energy difference, determined from optical and electrochemical measurements, corresponds qualitatively well with the values obtained from semiempirical calculations. An X-ray structural determination was performed on oligoheterocycle 6 and the experimental and calculated data are compared.

  DOI：

  10.1002/(sici)1521-3765(19981102)4:11<2211::aid-chem2211>3.0.co;2-7

文献信息

• Synthesis and Characterization of Mixed Oligoheterocycles Based on End-capped Oligothiophenes
  作者：Ullrich Mitschke、Elena Mena Osteritz、Tony Debaerdemaeker、Moritz Sokolowski、Peter Bäuerle

  DOI：10.1002/(sici)1521-3765(19981102)4:11<2211::aid-chem2211>3.0.co;2-7

  日期：1998.11.2

  A homologous series of mixed oligoheterocycles 2-6, based on the end-capped quinquethiophene EC5T 1, was synthesized by the introduction of electronegative heteroatoms, such as oxygen and nitrogen, into the conjugated Jc-system. This led to novel structures in which the central thiophene unit of the parent compound 1 is substituted by other heterocycles (thiazole, 1,3,4-thiadiazole, furan, oxazole, Id,4-oxadiazole) that have a more pronounced acceptor character. The characterization of the optical and electrochemical properties clearly reveal the influence of the heteroatoms on the electronic properties. The electron-withdrawing character of the central heterocycles renders the oxidation of the oligomer more difficult while reduction is facilitated. Moreover, in some cases a hypsochromic shift of the longest-wavelength absorption and emission is observed along with a significant enhancement of the fluorescence quantum yield in solution and in the solid state. The HOMO/LUMO energy difference, determined from optical and electrochemical measurements, corresponds qualitatively well with the values obtained from semiempirical calculations. An X-ray structural determination was performed on oligoheterocycle 6 and the experimental and calculated data are compared.