1,3-bis(5-bromothiophen-2-yl)-5-(n-dodecyl)thieno[3,4-c]pyrrole-4,6-dione | 1286745-62-7

• 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: 1,3-bis(5-bromothiophen-2-yl)-5-(n-dodecyl)thieno[3,4-c]pyrrole-4,6-dione
• 英文别名: 1,3-di(2-bromothien-5-yl)-5-dodecylthieno[3,4-c]pyrrole-4,6-dione；1,3-Bis(5-bromothiophen-2-yl)-5-dodecylthieno[3,4-c]pyrrole-4,6-dione；1,3-bis(5-bromothiophen-2-yl)-5-dodecylthieno[3,4-c]pyrrole-4,6-dione
• CAS: 1286745-62-7
• 化学式: C₂₆H₂₉Br₂NO₂S₃
• 分子量: 643.528
• InChiKey: BGHSTMKGNVWHRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-噻吩二羧酸酐 在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 硫酸 、 溴 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 氯仿 、 甲苯 为溶剂， 反应 16.0h， 生成 1,3-bis(5-bromothiophen-2-yl)-5-(n-dodecyl)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

• NOVEL PHOTOACTIVE POLYMERS
  申请人：Leclerc Mario

  公开号：US20130048075A1

  公开（公告）日：2013-02-28

  Photoactive polymers comprising first and second co-monomer repeat units, the first co-monomer repeat unit comprising a moiety selected from the group consisting of an alkylthieno[3,4-c]pyrrole-4,6-dione moiety and a 1,3-dithiophene-5-alkylthieno[3,4-c]pyrrole-4,6-dione moiety, and the second co-monomer repeat unit comprising a moiety selected from the group consisting of a 4,4′-dialkyl-dithieno[3,2-b:2′3′-d]silole moiety, an ethylene moiety, a thiophene moiety, an N-alkylcarbazole moiety, an N-(1-alkyl)dithieno[3,2-b:2′3′-d]pyrrole moiety and a 4,8-dialkyloxylbenzo[1,2-b:3,4-b]dithiophene moiety are described herein. These polymers are suitable for use in photovoltaic cells and field effect transistors.

  本文描述了包含第一和第二共聚单体重复单元的光致聚合物，其中第一共聚单体重复单元包括从羧基[3,4-c]吡咯-4,6-二酮基团和1,3-二硫杂吡咯-5-烷基[3,4-c]吡咯-4,6-二酮基团中选择的基团，而第二共聚单体重复单元包括从4,4'-二烷基-二硫杂吡咯[3,2-b:2'3'-d]硅烷基团、乙烯基团、噻吩基团、N-烷基咔唑基团、N-(1-烷基)二硫杂吡咯[3,2-b:2'3'-d]吡咯基团和4,8-二烷氧基苯并[1,2-b:3,4-b]二噻吩基团中选择的基团。这些聚合物适用于光伏电池和场效应晶体管。
• FLUORENE-CONTAINING ORGANIC SEMICONDUCTOR MATERIAL, PREPARATION METHOD AND USE THEREOF
  申请人：Zhou Mingjie

  公开号：US20130172508A1

  公开（公告）日：2013-07-04

  A fluorene-containing organic semiconductor material, preparation method and use thereof are provided. Said fluorene-containing organic semiconductor material has the following formula (P), wherein n is an integer of 1-100; m is an integer of 1-20; x and y are positive real number, and x+y=1; R 1 and R 2 are respectively H, F, CN, C 1 -C 40 linear or branched alkyl or alkoxyl, aryl or heteroaryl groups; R 3 is H, C 1 -C 20 alkyl. Said fluorene organic semiconductor material has a high carrier mobility, strong light absorbency and broad light absorption region, which improves utilization ratio to the sunlight.
• US8816035B2
  申请人：——

  公开号：US8816035B2

  公开（公告）日：2014-08-26
• Thieno[3,4-<i>c</i>]pyrrole-4,6-dione-Based Polymer Semiconductors: Toward High-Performance, Air-Stable Organic Thin-Film Transistors
  作者：Xugang Guo、Rocio Ponce Ortiz、Yan Zheng、Myung-Gil Kim、Shiming Zhang、Yan Hu、Gang Lu、Antonio Facchetti、Tobin J. Marks

  DOI：10.1021/ja205398u

  日期：2011.8.31

  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.