5-tetradecyl[3,4-c]thienopyrrole-4,6-dione | 1355961-61-3

• 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-tetradecyl[3,4-c]thienopyrrole-4,6-dione
• 英文别名: 5-Tetradecylthieno[3,4-c]pyrrole-4,6-dione；5-tetradecylthieno[3,4-c]pyrrole-4,6-dione
• CAS: 1355961-61-3
• 化学式: C₂₀H₃₁NO₂S
• 分子量: 349.538
• InChiKey: CFSKNWSSXQUUKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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-tetradecyl[3,4-c]thienopyrrole-4,6-dione 在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 溴 、 溶剂黄146 、 三氟乙酸 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：

  3,4-噻吩二羧酸酐 在 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 28.0h， 生成 5-tetradecyl[3,4-c]thienopyrrole-4,6-dione
  参考文献：
  名称：

  聚（5-烷基-噻吩并[3,4- c ]吡咯-4,6-二酮）：π-共轭氧化还原聚合物作为锂离子电池负极材料的研究

  摘要：

  在过去的几年中，已经研究了有机聚合物作为活性电极材料，尽管已经开发出了具有高能量密度和可调节氧化还原电位的材料，但是它们溶解于电解质中以及其低电导率限制了它们在可再充电电池中的使用。为了克服这些缺点，基于5-烷基-噻吩并[3,4- c]的七种n型π-共轭氧化还原聚合物已经开发了用于可再充电电池负极材料的]吡咯-4，6-二酮。已经证明了羰基对这些聚合物的电化学活性的作用，以及烷基链和共聚单体单元对其电化学性能的影响。该聚合物的氧化还原电位已显示以改变在一定范围的400毫伏，并用1.55 V的合适的氧化还原电势的聚合物对比对于Li / Li +为锂离子电池的负极已经找到。

  DOI：

  10.1039/c7ta03786d

文献信息

• 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。
• US9505876B2
  申请人：——

  公开号：US9505876B2

  公开（公告）日：2016-11-29
• [EN] PREPARATION OF HIGH MOLECULAR WEIGHT POLYMERS 8Y DIRECT ARYLATION AND HETEROARYLATION<br/>[FR] PRÉPARATION DE POLYMÈRES DE POIDS MOLÉCULAIRE ÉLEVÉ PAR ARYLATION ET HÉTÉROARYLATION DIRECTES
  申请人：UNIV LAVAL

  公开号：WO2013056355A1

  公开（公告）日：2013-04-25

  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