2-ethynyl-4,5-dihexylbenzo[1,2-b:4,3-b']dithiophene | 960074-55-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2-ethynyl-4,5-dihexylbenzo[1,2-b:4,3-b']dithiophene
• 英文别名: 2-Ethynyl-4,5-dihexylthieno[3,2-e][1]benzothiole
• CAS: 960074-55-9
• 化学式: C₂₄H₃₀S₂
• 分子量: 382.634
• InChiKey: BGBYJOZTVJUBNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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-ethynyl-4,5-dihexylbenzo[1,2-b:4,3-b']dithiophene 、 1,2-bis(7-iodo-4,5-dihexylbenzo[1,2-b:4,3-b']dithiophen-2-yl)acetylene 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以73%的产率得到7-[2-(4,5-Dihexylthieno[3,2-e][1]benzothiol-2-yl)ethynyl]-2-[2-[7-[2-(4,5-dihexylthieno[3,2-e][1]benzothiol-2-yl)ethynyl]-4,5-dihexylthieno[3,2-e][1]benzothiol-2-yl]ethynyl]-4,5-dihexylthieno[3,2-e][1]benzothiole
  参考文献：
  名称：

  Synthesis and Properties of a Series of Well-Defined and Polydisperse Benzo[1,2-b:4,3-b‘]dithiophene Oligomers

  摘要：

  [Graphics]Monodisperse and polydisperse oligomers of benzo[1,2-b:4,3-b']dithiophene (BDT) (1-14), including three types of oligomers with different spacers combining BDT units (direct linkage, vinylene spacers, and ethynylene spacers), were synthesized, and their thermal, optical, and electrochemical properties were investigated. The oligomers were synthesized using Suzuki, Stille, Wittig, and Sonogashira coupling reactions. All of the monodisperse oligomers showed high melting points and 5% weight loss temperatures (T-d > 400 degrees C). The fluorescence maxima of all oligomers were red-shifted, and the emission colors varied from blue to yellow as the chain lengths-and thus the conjugation lengths-increased. The vinylene-bridged oligomers emitted at longer wavelengths than the direct-linked and ethynylene-bridged oligomers. UV-vis absorption spectra in toluene solution indicated an effective conjugation length of about six BDT units for polydisperse oligomer 5. Cyclic voltammetry measurement indicated that tetramer 3 had high electrochemical stability. Although tetramer 3 and vinylene-bridged tetramer 8 exhibited reversible oxidation waves, ethynylene-bridged tetramer 13 showed an irreversible oxidation process. Each type of monodisperse oligomer exhibited higher HOMO levels with increasing chain length.

  DOI：

  10.1021/jo071062b
• 作为产物：
  描述：

  2-[(trimethylsilyl)ethynyl]-4,5-dihexylbenzo[1,2-b:4,3-b']dithiophene 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 17.0h， 以73%的产率得到2-ethynyl-4,5-dihexylbenzo[1,2-b:4,3-b']dithiophene
  参考文献：
  名称：

  Synthesis and Properties of a Series of Well-Defined and Polydisperse Benzo[1,2-b:4,3-b‘]dithiophene Oligomers

  摘要：

  [Graphics]Monodisperse and polydisperse oligomers of benzo[1,2-b:4,3-b']dithiophene (BDT) (1-14), including three types of oligomers with different spacers combining BDT units (direct linkage, vinylene spacers, and ethynylene spacers), were synthesized, and their thermal, optical, and electrochemical properties were investigated. The oligomers were synthesized using Suzuki, Stille, Wittig, and Sonogashira coupling reactions. All of the monodisperse oligomers showed high melting points and 5% weight loss temperatures (T-d > 400 degrees C). The fluorescence maxima of all oligomers were red-shifted, and the emission colors varied from blue to yellow as the chain lengths-and thus the conjugation lengths-increased. The vinylene-bridged oligomers emitted at longer wavelengths than the direct-linked and ethynylene-bridged oligomers. UV-vis absorption spectra in toluene solution indicated an effective conjugation length of about six BDT units for polydisperse oligomer 5. Cyclic voltammetry measurement indicated that tetramer 3 had high electrochemical stability. Although tetramer 3 and vinylene-bridged tetramer 8 exhibited reversible oxidation waves, ethynylene-bridged tetramer 13 showed an irreversible oxidation process. Each type of monodisperse oligomer exhibited higher HOMO levels with increasing chain length.

  DOI：

  10.1021/jo071062b