1,3-dibromo-5-(n-decyl)thieno[3,4-c]pyrrole-4,6-dione | 1327275-52-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 1,3-dibromo-5-(n-decyl)thieno[3,4-c]pyrrole-4,6-dione
• 英文别名: 1,3-Dibromo-5-decylthieno[3,4-c]pyrrole-4,6-dione
• CAS: 1327275-52-4
• 化学式: C₁₆H₂₁Br₂NO₂S
• 分子量: 451.222
• InChiKey: INQNRTKYRYGXOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  65.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-dibromo-5-(n-decyl)thieno[3,4-c]pyrrole-4,6-dione 在 bis-triphenylphosphine-palladium(II) chloride 、 溴 、 溶剂黄146 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 16.0h， 生成 1,3-bis[5-bromo-3-(n-decyl)thiophen-2-yl]-5-(n-decyl)thieno[3,4-c]pyrrole-4,6-dione
  参考文献：
  名称：

  Thieno[3,4-c]pyrrole-4,6-dione-Based Polymer Semiconductors: Toward High-Performance, Air-Stable Organic Thin-Film Transistors

  摘要：

  We report a new,p-type semiconducting polymer family based on the thieno[3,4-c]pyrrole-4,6-dione (TPD) building block, which exhibits good processability as well as good mobility and lifetime stability in thin-film transistors (TFTs). TPD homopolymer P1 was synthesized via Yamamoto coupling, whereas copolymers P2-P8 were synthesized via Stile coupling. All of these polymers were characterized by chemical analysis as well as thermal analysis, optical spectroscopy, and cyclic voltammetry. P2-P7 have lower-lying HOMOs than does P3HT by 0.24-0.57 eV, depending on the donor counits, and exhibit large oscillator strengths in the visible region with similar optical band gaps throughout the series (similar to 1.80 eV). The electron-rich character of the dialkoxybithiophene counits in P8 greatly compresses the band gap, resulting in the lowest E-g(opt) in the series (1.66 eV), but also raising the HOMO energy to -5.11 eV. Organic thin-film transistor (OTFT) electrical characterization indicates that device performance is very sensitive to the oligothiophene conjugation length, but also to the solubilizing side chain substituEnts (length, positional pattern). The corresponding thin-film microstructures and morphologies were investigated by XRD and AFM to correlate with the OTFT performance. By strategically varying the oligothiophene donor conjugation length and optimizing the solubilizing side chains, a maximum OTFT hole mobility of similar to 0.6 cm(2) V-1 s(-1) is achieved for P4-based devices. OTFT environmental (storage) and operational (bias) stability in ambient was investigated, and enhanced performance is observed due to the low-lying HOMOs. These results indicate that the TPD is an excellent building block for constructing high-performance polymers for p-type transistor applications due to the excellent processability, substantial hole mobility, and good device stability.

  DOI：

  10.1021/ja205398u
• 作为产物：
  描述：

  5-Decylthieno[3,4-c]pyrrole-4,6-dione 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 三氟乙酸 作用下， 以78%的产率得到1,3-dibromo-5-(n-decyl)thieno[3,4-c]pyrrole-4,6-dione
  参考文献：
  名称：

  Thieno[3,4-c]pyrrole-4,6-dione-Based Polymer Semiconductors: Toward High-Performance, Air-Stable Organic Thin-Film Transistors

  摘要：

  We report a new,p-type semiconducting polymer family based on the thieno[3,4-c]pyrrole-4,6-dione (TPD) building block, which exhibits good processability as well as good mobility and lifetime stability in thin-film transistors (TFTs). TPD homopolymer P1 was synthesized via Yamamoto coupling, whereas copolymers P2-P8 were synthesized via Stile coupling. All of these polymers were characterized by chemical analysis as well as thermal analysis, optical spectroscopy, and cyclic voltammetry. P2-P7 have lower-lying HOMOs than does P3HT by 0.24-0.57 eV, depending on the donor counits, and exhibit large oscillator strengths in the visible region with similar optical band gaps throughout the series (similar to 1.80 eV). The electron-rich character of the dialkoxybithiophene counits in P8 greatly compresses the band gap, resulting in the lowest E-g(opt) in the series (1.66 eV), but also raising the HOMO energy to -5.11 eV. Organic thin-film transistor (OTFT) electrical characterization indicates that device performance is very sensitive to the oligothiophene conjugation length, but also to the solubilizing side chain substituEnts (length, positional pattern). The corresponding thin-film microstructures and morphologies were investigated by XRD and AFM to correlate with the OTFT performance. By strategically varying the oligothiophene donor conjugation length and optimizing the solubilizing side chains, a maximum OTFT hole mobility of similar to 0.6 cm(2) V-1 s(-1) is achieved for P4-based devices. OTFT environmental (storage) and operational (bias) stability in ambient was investigated, and enhanced performance is observed due to the low-lying HOMOs. These results indicate that the TPD is an excellent building block for constructing high-performance polymers for p-type transistor applications due to the excellent processability, substantial hole mobility, and good device stability.

  DOI：

  10.1021/ja205398u

文献信息

• COPOLYMER, ORGANIC SEMICONDUCTOR MATERIAL, ORGANIC ELECTRICAL DEVICE, AND PHOTOVOLTAIC MODULE
  申请人：MITSUBISHI CHEMICAL CORPORATION

  公开号：US20150094436A1

  公开（公告）日：2015-04-02

  A copolymer containing a repeating unit having a dioxopyrrole condensed ring skeleton and a repeating unit having a dithieno condensed ring skeleton and also having a specific substituent is provided.

  提供一种共聚物，其中包含具有二氧杂吡咯环骨架的重复单元和具有二噻吩环骨架的重复单元，并且具有特定取代基。
• COPOLYMER, ORGANIC SEMICONDUCTOR MATERIAL, ORGANIC ELECTRICAL DEVICE, AND SOLAR CELL MODULE
  申请人：Mitsubishi Chemical Corporation

  公开号：EP2857429A1

  公开（公告）日：2015-04-08

  It is an object of the present invention to provide a copolymer that can be used as a semiconductor material and is highly stable in solution. The problem is solved by a copolymer containing a repeating unit having a dioxopyrrole condensed ring skeleton and a repeating unit having a dithieno condensed ring skeleton and also having a specific substituent.

  本发明的目的是提供一种可用作半导体材料且在溶液中高度稳定的共聚物。要解决这个问题，就需要一种共聚物，该共聚物含有一个具有二氧吡咯缩合环骨架的重复单元和一个具有二噻吩缩合环骨架的重复单元，并且还具有一个特定的取代基。
• US9249257B2
  申请人：——

  公开号：US9249257B2

  公开（公告）日：2016-02-02