2,5-bis(3-dodecyl-5-(tributylstannyl)thiophen-2-yl)thieno[3,2-b]thiophene | 1407188-15-1

• 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: 2,5-bis(3-dodecyl-5-(tributylstannyl)thiophen-2-yl)thieno[3,2-b]thiophene
• CAS: 1407188-15-1
• 化学式: C₆₂H₁₀₈S₄Sn₂
• 分子量: 1219.22
• InChiKey: HZRNZZRWBOMITG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.46
• 重原子数：
  68.0
• 可旋转键数：
  44.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-dodecyl-5H-benzo[b]carbazol-3-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate 、 2,5-bis(3-dodecyl-5-(tributylstannyl)thiophen-2-yl)thieno[3,2-b]thiophene 在 四(三苯基膦)钯 、 N,N-二甲基甲酰胺 、 lithium chloride 作用下， 反应 24.0h， 以77%的产率得到2,5-bis(5-dodecyl-8,9-dipropyl-5H-benzo[b]carbazol-3-yl)thieno[3,2-b]thiophene
  参考文献：
  名称：

  相标记辅助合成苯并[ b ]咔唑端基寡聚噻吩

  摘要：

  在苯并[ b ]咔唑的新合成中，已使用相标记的引入和去除来引发环化事件。该方法已被用于新的苯并[ b ]咔唑封端的低聚噻吩的标签辅助方法中，用于半导体的初步评估。

  DOI：

  10.1021/ol302748h
• 作为产物：
  描述：

  2,5-bis(3-dodecylthiophen-2-yl)thieno[3,2-b]thiophene 、 三丁基氯化锡 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以100%的产率得到2,5-bis(3-dodecyl-5-(tributylstannyl)thiophen-2-yl)thieno[3,2-b]thiophene
  参考文献：
  名称：

  相标记辅助合成苯并[ b ]咔唑端基寡聚噻吩

  摘要：

  在苯并[ b ]咔唑的新合成中，已使用相标记的引入和去除来引发环化事件。该方法已被用于新的苯并[ b ]咔唑封端的低聚噻吩的标签辅助方法中，用于半导体的初步评估。

  DOI：

  10.1021/ol302748h

文献信息

• The Good Host: Formation of Discrete One-Dimensional Fullerene “Channels” in Well-Ordered Poly(2,5-bis(3-alkylthiophen-2-yl)thieno[3,2-<i>b</i>]thiophene) Oligomers
  作者：Lei Zhang、Feng Liu、Ying Diao、Hilary S. Marsh、Nicholas S. Colella、Arthi Jayaraman、Thomas P. Russell、Stefan C. B. Mannsfeld、Alejandro L. Briseno

  DOI：10.1021/ja510976n

  日期：2014.12.31

  Due to the unique crystallinity of poly(2,5-bis(3-alkylthiophen-2-yl)thieno[3,2-b]thiophene) (PBTTT), it is an excellent model polymer to study the structureproperty relationship in organic devices, especially those relying on junctions of electron- and hole-transporting materials. Here, we report the synthesis and characterization of a series of monodisperse PBTTT oligothiophenes (n = 15) and systematically examine the evolution of crystalline behavior, morphology, and interaction with [6,6]-phenyl C-61-butyric acid methyl ester (PCBM) as the molecular conjugation length increases. We discovered that fullerene intercalation occurs when there is enough free volume between the side chains to accommodate the fullerene molecule. The intercalation of PCBM is observed beyond BTTT-2 and longer oligomers, likely similar to that of PBTTT. Interestingly, both experiments and molecular simulations show that PCBM intercalation also appears to catalyze a more efficient packing of the BTTT-2 dimers. Crystal structure analysis revealed that the straight BTTT-2 side chains form one-dimensional (1D) channels that could perfectly host PCBM but, in the pure material, accommodate the interdigitated side chains from adjacent layers. In the blend with PCBM, these channels are maintained and enable the cocrystallization and intercalation of PCBM. This is the first time the actual sublattice cell of PCBM has been determined from the X-ray data, and demonstration the utility of the oligomers as model systems for their polymer counterparts. Among the organic photovoltaic devices (OPVs) made from the BTTT oligomers and [6,6]-phenyl C(71-)butyric acid methyl ester (PC71BM) blends, the ones containing the BTTT-2 dimer exhibit the highest performance.