1,3-dibromo-5-tetradecyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione | 1327275-53-5

• 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-tetradecyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione
• 英文别名: 1,3-dibromo-5-(n-tetradecyl)thieno[3,4-c]pyrrole-4,6-dione
• CAS: 1327275-53-5
• 化学式: C₂₀H₂₉Br₂NO₂S
• 分子量: 507.33
• InChiKey: IUOMUJRESPKVRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.57
• 重原子数：
  26.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,3-dibromo-5-tetradecyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-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-tetradecyl)thiophen-2-yl]-5-(n-tetradecyl)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-tetradecyl[3,4-c]thienopyrrole-4,6-dione 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 三氟乙酸 作用下， 以76%的产率得到1,3-dibromo-5-tetradecyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-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

• Importance of the Donor:Fullerene Intermolecular Arrangement for High-Efficiency Organic Photovoltaics
  作者：Kenneth R. Graham、Clement Cabanetos、Justin P. Jahnke、Matthew N. Idso、Abdulrahman El Labban、Guy O. Ngongang Ndjawa、Thomas Heumueller、Koen Vandewal、Alberto Salleo、Bradley F. Chmelka、Aram Amassian、Pierre M. Beaujuge、Michael D. McGehee

  DOI：10.1021/ja502985g

  日期：2014.7.9

  PV devices where fullerene derivatives serve as the electron-accepting materials. Furthermore, external quantum efficiency measurements of the charge-transfer state and solid-state two-dimensional (2D) (13)C(1)H} heteronuclear correlation (HETCOR) NMR analyses support that a specific polymer:fullerene arrangement is present for the highest performing PBDTTPD derivative, in which the fullerene is in

  假设有机光伏 (OPV) 材料系统的性能在很大程度上取决于供体：富勒烯界面处的分子间排列。对聚合物中使用的一些最有效的聚合物的回顾：富勒烯 PV 器件，结合对报告的聚合物供体材料的分析，其中使用相同的共轭骨架与不同的烷基取代基，支持这一假设。具体而言，文献表明，更高性能的供体-受体类型聚合物通常具有可与富勒烯衍生物在空间上发生相互作用的受体部分，而相应的供体部分往往具有在空间上阻碍与富勒烯相互作用的支链烷基取代基。进一步探讨最有益聚合物的想法：富勒烯排列涉及富勒烯与受体部分的对接，受体部分是苯并[1,2-b:4,5-b']二噻吩-噻吩并[3,4-c]吡咯-4,6-二酮聚合物（PBDTTPD衍生物）家族) 是在各种 PV 设备类型中合成和测试的，聚合物的聚集状态大不相同。与我们的假设一致，具有更立体可及的受体部分和更多空间受阻供体部分的 PBDTTPD 衍生物在体异质结、双层和低聚合物浓度 PV