3''-formyl-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene | 860116-63-8

• 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: 3''-formyl-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene
• 英文别名: 2,5-Bis(5-thiophen-2-ylthiophen-2-yl)thiophene-3-carbaldehyde；2,5-bis(5-thiophen-2-ylthiophen-2-yl)thiophene-3-carbaldehyde
• CAS: 860116-63-8
• 化学式: C₂₁H₁₂OS₅
• 分子量: 440.656
• InChiKey: LKGPGOPHSDCHHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  158
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3''-formyl-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene 、 bis(3-butyl-4-methyl-2-pyrrolyl)methane 在 三氟化硼乙醚 、 四氯苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 4.83h， 以56%的产率得到2,8,12,18-tetra-n-butyl-3,7,13,17-tetramethyl-5,15-bis[2',2'';5'',2''';5''',2'''';5'''',2''''']quinquethiophen-3'''-yl-porphyrin
  参考文献：
  名称：

  The design and synthesis of porphyrin/oligiothiophene hybrid monomers

  摘要：

  为了构建基于卟啉官能化聚噻吩的高效光伏电池，我们集中研究了三种单体类型的合成路线。通过控制单体的几何结构，这些材料的氧化应该能够产生具有不同建筑结构的聚合物，从而导致不同的光电特性。采用Wittig反应策略使我们能够获得卟啉部分通过烯烃连接到噻吩β位的单体。此外，还使用卟啉缩合方法构建了α-噻吩间位取代卟啉的单体。另一组单体也是通过卟啉缩合路线制备的，但使用了β-甲酰基噻吩。通过利用不同的甲酰基低聚噻吩，我们能够生成一系列单体，以用于控制卟啉在聚噻吩矩阵中的负载。

  DOI：

  10.1039/b502517f
• 作为产物：
  描述：

  3'-formyl-2,2':5',2''-terthiophene 在 四(三苯基膦)钯 N-溴代丁二酰亚胺(NBS) 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 3''-formyl-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene
  参考文献：
  名称：

  A modular procedure for the synthesis of functionalised β-substituted terthiophene monomers for conducting polymer applications

  摘要：

  An efficient modular strategy has been developed for the synthesis of beta-functionalised terthiophene monomers using Suzuki-Miyaura and Wittig/Horner-Emmons chemistries. This paper discusses the problems encountered with converting the beta-terthiophene aldehyde building block to the beta-terthiophene phosphonium salt and the use of this material in a Wittig condensation. An improved strategy using the beta-terthiophene phosphonate building block constructed via Suzuki-Miyaura coupling protocols was developed. We have synthesised and characterised a broad range of functionalised terthiophene materials that have been designed for specific end-use applications. The availability of these building blocks has dramatically increased access to a range of key monomers. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.022

文献信息

• The design and synthesis of porphyrin/oligiothiophene hybrid monomers
  作者：Gavin E. Collis、Wayne M. Campbell、David L. Officer、Anthony K. Burrell

  DOI：10.1039/b502517f

  日期：——

  In an effort to build effective photovoltaic cells based on porphyrin-functionalised polythiophenes we have focused on synthetic routes to three monomer types. By controlling the geometric structure of the monomer, oxidation of these materials should produce polymers with different architectural structures, and as a result, different opto-electronic properties. Employing Wittig protocols allowed access to monomers in which the porphyrin moiety is connected to the β-position of the thiophene via an alkene linkage. In addition, monomers were constructed using porphyrin condensation methods to afford α-thiophene meso-substituted porphryins. Another set of monomers was also prepared via porphyrin condensation routes, but instead utilising β-formylthiophenes. By utilising different formyloligothiophenes we were able to generate a series of monomers that can be used to control the loading of the porphyrin in the polythiophene matrix.

  为了构建基于卟啉官能化聚噻吩的高效光伏电池，我们集中研究了三种单体类型的合成路线。通过控制单体的几何结构，这些材料的氧化应该能够产生具有不同建筑结构的聚合物，从而导致不同的光电特性。采用Wittig反应策略使我们能够获得卟啉部分通过烯烃连接到噻吩β位的单体。此外，还使用卟啉缩合方法构建了α-噻吩间位取代卟啉的单体。另一组单体也是通过卟啉缩合路线制备的，但使用了β-甲酰基噻吩。通过利用不同的甲酰基低聚噻吩，我们能够生成一系列单体，以用于控制卟啉在聚噻吩矩阵中的负载。
• A modular procedure for the synthesis of functionalised β-substituted terthiophene monomers for conducting polymer applications
  作者：Gavin E. Collis、Anthony K. Burrell、Esther J. Blandford、David L. Officer

  DOI：10.1016/j.tet.2007.08.022

  日期：2007.11

  An efficient modular strategy has been developed for the synthesis of beta-functionalised terthiophene monomers using Suzuki-Miyaura and Wittig/Horner-Emmons chemistries. This paper discusses the problems encountered with converting the beta-terthiophene aldehyde building block to the beta-terthiophene phosphonium salt and the use of this material in a Wittig condensation. An improved strategy using the beta-terthiophene phosphonate building block constructed via Suzuki-Miyaura coupling protocols was developed. We have synthesised and characterised a broad range of functionalised terthiophene materials that have been designed for specific end-use applications. The availability of these building blocks has dramatically increased access to a range of key monomers. (c) 2007 Elsevier Ltd. All rights reserved.