5-(2-hexyldecyl)thieno[3,4-c]pyrrole-4,6-dione | 1355961-59-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-(2-hexyldecyl)thieno[3,4-c]pyrrole-4,6-dione
• 英文别名: 5-(2-Hexyldecyl)thieno[3,4-c]pyrrole-4,6-dione
• CAS: 1355961-59-9
• 化学式: C₂₂H₃₅NO₂S
• 分子量: 377.591
• InChiKey: YEPZNGBDKUURIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  5-(2-hexyldecyl)thieno[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81%的产率得到1,3-二溴-5-(2-己基癸基)-4H-噻吩并[3,4-C]吡咯-4,6(5H)-二酮
  参考文献：
  名称：

  基于两个具有互补吸收和平衡结晶性的非富勒烯受体的三元有机太阳能电池

  摘要：

  三元共混结构已被证明是提高有机太阳能电池功率转换效率的有效方法。一种有效的提高三元太阳能电池功率转换效率的方法是基于两个具有互补吸收范围和平衡结晶度的非富勒烯受体。在这项工作中，我们将高结晶度的小分子受体C8IDTT-4Cl与合适的烷基侧链引入到共轭聚合物供体PBDT-TPD和稠环电子受体ITIC-4F的低结晶混合物中。基于PBDT‐TPD：ITIC‐4F：C8IDTT‐4Cl共混物的三元器件具有9.51％的最佳功率转换效率，同时短路电流密度提高到18.76 mA·cm –2填充因子高达67.53％。C8IDTT-4Cl的吸收起始点位于900 nm，因此良好互补的光吸收有益于光电流。此外，三元器件中高结晶度的C8IDTT-4Cl的存在有助于调节结晶度，改善异质结形态和堆叠结构，从而实现更高的电荷迁移率和更好的性能。

  DOI：

  10.1002/cjoc.201900554
• 作为产物：
  描述：

  3,4-噻吩二羧酸酐 在 氯化亚砜 作用下， 以 甲苯 为溶剂， 生成 5-(2-hexyldecyl)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

• Synthesis of 5-Alkyl[3,4-c]thienopyrrole-4,6-dione-Based Polymers by Direct Heteroarylation
  作者：Philippe Berrouard、Ahmed Najari、Agnieszka Pron、David Gendron、Pierre-Olivier Morin、Jean-Rémi Pouliot、Justine Veilleux、Mario Leclerc

  DOI：10.1002/anie.201106411

  日期：2012.2.27

  Don't stand Stille: A direct heteroarylation polycondensation reaction was used for the synthesis of high‐molecular‐weight thienopyrroledione‐based polymers (see scheme) in an impressive yield (up to 96 %) and in only a few synthetic steps. This new method is an alternative to the standard Stille coupling reaction and thus avoids formation of toxic tin by‐products.

  不要停滞不前：直接杂芳基缩聚反应用于高分子量噻吩并吡咯二酮基聚合物的合成（见方案），收率很高（高达96％），而且仅需几个合成步骤。此新方法是标准Stille偶联反应的替代方法，因此避免了有毒锡副产物的形成。
• PREPARATION OF HIGH MOLECULAR WEIGHT POLYMERS BY DIRECT ARYLATION AND HETEROARYLATION
  申请人：UNIVERSITE LAVAL

  公开号：US20140371409A1

  公开（公告）日：2014-12-18

  A method for preparing polymers by direct heteroarylation or arylation polycondensation is described herein. The method includes preparing a reaction mixture including at least a monomer to be polymerized, a catalyst and a ligand; heating the reaction mixture, and, optionally, end-capping the reaction mixture.

  本文描述了一种通过直接杂环化或芳基化聚合制备聚合物的方法。该方法包括制备反应混合物，其中至少包括一个要聚合的单体、一个催化剂和一个配体；加热反应混合物，以及可选地对反应混合物进行端基化处理。
• Preparation of high molecular weight polymers by direct arylation and heteroarylation
  申请人：UNIVERSITE LAVAL

  公开号：US10584203B2

  公开（公告）日：2020-03-10

  A method for preparing polymers by direct heteroarylation or arylation polycondensation is described herein. The method includes preparing a reaction mixture including at least a monomer to be polymerized, a catalyst and a ligand; heating the reaction mixture; and, optionally, end-capping the reaction mixture.

  本文描述了一种通过直接杂芳基化或芳基化缩聚制备聚合物的方法。该方法包括制备一种反应混合物，其中至少包括一种待聚合的单体、一种催化剂和一种配体；加热反应混合物；以及，可选地，对反应混合物进行末端封端。
• Robust Direct (Hetero)arylation Polymerization in Biphasic Conditions
  作者：François Grenier、Karine Goudreau、Mario Leclerc

  DOI：10.1021/jacs.6b12955

  日期：2017.2.22

  The synthesis of conjugated polymers from direct (hetero)arylation polymerization (DHAP) has been achieved for the first time using biphasic water/toluene conditions. This protocol is robust enough to form polymers even when air is introduced in the system. General reactivity is demonstrated for a single set of polymerization conditions with thienyl- or phenyl-based substrates, whether they are electron-rich or electron-poor. Complete characterization from differential scanning calorimetry and H-1 NMR and UV-vis-NIR spectroscopies is presented, demonstrating this DHAP protocol offers comparable or better properties than the very best values published thus far. High molecular weights are obtained, showcasing the perfect equilibrium of reactivity and selectivity attained with this method. Moreover, this efficient and versatile methodology, which also uses low-cost, "wet" reagents, is scalable and done at ambient pressure.
• US9505876B2
  申请人：——

  公开号：US9505876B2

  公开（公告）日：2016-11-29