5'-bromo-3,4-dimethyl-[2,2'-bithiophene]-5-carbaldehyde | 1384127-58-5

• 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: 5'-bromo-3,4-dimethyl-[2,2'-bithiophene]-5-carbaldehyde
• 英文别名: 5-(5-Bromothiophen-2-yl)-3,4-dimethylthiophene-2-carbaldehyde
• CAS: 1384127-58-5
• 化学式: C₁₁H₉BrOS₂
• 分子量: 301.228
• InChiKey: KZAMYJRIGHPRMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  73.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5'-bromo-3,4-dimethyl-[2,2'-bithiophene]-5-carbaldehyde 在 四(三苯基膦)钯 、 β-丙氨酸 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2,2'-[(3,4,3'''',4''''-tetramethyl-2,2':5',2'':5'',2''':5''',2''''-quinquethien-5,5''''-diyl)bis(methane-1-yl-1-ylidene)]dimalononitrile
  参考文献：
  名称：

  Correlation of π-Conjugated Oligomer Structure with Film Morphology and Organic Solar Cell Performance

  摘要：

  The novel methyl-substituted dicyanovinyl-capped quinquethiophenes 1-3 led to highly efficient organic solar cells with power conversion efficiencies of 4.8-6.9%. X-ray analysis of single crystals and evaporated neat and blend films gave insights into the packing and morphological behavior of the novel compounds that rationalized their improved photovoltaic performance.

  DOI：

  10.1021/ja302320c
• 作为产物：
  描述：

  3,4-dimethyl-2,2'-bithiophene-5-carbaldehyde 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 58.0h， 以92%的产率得到5'-bromo-3,4-dimethyl-[2,2'-bithiophene]-5-carbaldehyde
  参考文献：
  名称：

  Correlation of π-Conjugated Oligomer Structure with Film Morphology and Organic Solar Cell Performance

  摘要：

  The novel methyl-substituted dicyanovinyl-capped quinquethiophenes 1-3 led to highly efficient organic solar cells with power conversion efficiencies of 4.8-6.9%. X-ray analysis of single crystals and evaporated neat and blend films gave insights into the packing and morphological behavior of the novel compounds that rationalized their improved photovoltaic performance.

  DOI：

  10.1021/ja302320c

文献信息

• Syntheses and Photovoltaic Properties of Octyl Cyanoacetate Terminated Small Molecules Based on Benzo[1,2-b:4,5-b’]dithiophene for OPVs
  作者：Min-Ah Park、Sangman Park、Sung Kwon Hong、Dong Hak Suh、Changjin Lee、Sung Cheol Yoon

  DOI：10.1080/15421406.2014.937283

  日期：2014.9.2

  There have been tremendous efforts to synthesize photoactive materials that are consisted of both donor and acceptor components together to increase the power conversion efficiency (PCE) of organic photovoltaic cells (OPVs). In order to improve the performance of the OPVs, in this study, we proposed new A-D-A (Acceptor-Donor-Acceptor) type small molecular donors based on the donor unit of benzo[1,2-b:4.5-b']dithiophene (BDT) with an acceptor unit of alkyl cyanoacetate. We characterized prepared photoactive materials using H-1 NMR spectroscopy, DSC, CV (cyclic voltammetry), and UV/Vis spectroscopy. We also investigated the relationship between PCEs of OPVs and the active materials with variation of substituted methyl groups. The OPVs based on synthesized photoactive materials with different methyl substitutions showed different PCEs. Our results indicate that synthesized small molecular donor materials are promising donor materials for performance OPVs