2,6-bis(tributylstannyl)-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene | 1315511-12-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2,6-bis(tributylstannyl)-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene
• CAS: 1315511-12-6
• 化学式: C₄₉H₉₀S₂Sn₂
• 分子量: 980.806
• InChiKey: YEZLNWSQDJWQLA-UHFFFAOYSA-N

物化性质

• 沸点：
  790.4±70.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  17.4
• 重原子数：
  53
• 可旋转键数：
  32
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 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：

  2,6-bis(tributylstannyl)-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene 、 4-溴-7-甲基苯并[1,2,5]噻二唑 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 12.0h， 以98%的产率得到2,6-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[1,2-b;3,4-b']dithiophene)-4,7-benzo[2,1,3]thiadiazole
  参考文献：
  名称：

  Charge Photogeneration in Donor–Acceptor Conjugated Materials: Influence of Excess Excitation Energy and Chain Length

  摘要：

  We investigate the role of excess excitation energy on the nature of photoexcitations in donor-acceptor pi-conjugated materials. We compare the polymer poly(2,6-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[1,2-b;3,4-b']dithiophene)-4,7-benzo[2,1,3]thiadiazole) (PCPDTBT) and a short oligomer with identical constituents at different excitation wavelengths, from the near-infrared up to the ultraviolet spectral region. Ultrafast spectroscopic measurements clearly show an increased polaron pair yield for higher excess energies directly after photoexcitation when compared to the exciton population. This effect, already observable in the polymer, is even more pronounced for the shorter oligomer. Supported by quantum chemical simulations, we show that excitation in high-energy states generates electron and hole wave functions with reduced overlap, which likely act as precursors for the polaron pairs. Interestingly, in the oligomer we observe a lifetime of polaron pairs which is one order of magnitude longer. We suggest that this behavior results from the intermolecular nature of polaron pairs in oligomers. The study excludes the presence of carrier multiplication in these materials and highlights new aspects in the photophysics of donor-acceptor small molecules when compared to polymers. The former are identified as promising materials for efficient organic photovoltaics.

  DOI：

  10.1021/ja309252a

文献信息

• Charge Photogeneration in Donor–Acceptor Conjugated Materials: Influence of Excess Excitation Energy and Chain Length
  作者：Raphael Tautz、Enrico Da Como、Christian Wiebeler、Giancarlo Soavi、Ines Dumsch、Nils Fröhlich、Giulia Grancini、Sybille Allard、Ullrich Scherf、Giulio Cerullo、Stefan Schumacher、Jochen Feldmann

  DOI：10.1021/ja309252a

  日期：2013.3.20

  We investigate the role of excess excitation energy on the nature of photoexcitations in donor-acceptor pi-conjugated materials. We compare the polymer poly(2,6-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[1,2-b;3,4-b']dithiophene)-4,7-benzo[2,1,3]thiadiazole) (PCPDTBT) and a short oligomer with identical constituents at different excitation wavelengths, from the near-infrared up to the ultraviolet spectral region. Ultrafast spectroscopic measurements clearly show an increased polaron pair yield for higher excess energies directly after photoexcitation when compared to the exciton population. This effect, already observable in the polymer, is even more pronounced for the shorter oligomer. Supported by quantum chemical simulations, we show that excitation in high-energy states generates electron and hole wave functions with reduced overlap, which likely act as precursors for the polaron pairs. Interestingly, in the oligomer we observe a lifetime of polaron pairs which is one order of magnitude longer. We suggest that this behavior results from the intermolecular nature of polaron pairs in oligomers. The study excludes the presence of carrier multiplication in these materials and highlights new aspects in the photophysics of donor-acceptor small molecules when compared to polymers. The former are identified as promising materials for efficient organic photovoltaics.