1,3-二溴-5-(2-己基癸基)-4H-噻吩并[3,4-C]吡咯-4,6(5H)-二酮 | 1234306-57-0

• 物质功能分类: 医药中间体 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 1,3-二溴-5-(2-己基癸基)-4H-噻吩并[3,4-C]吡咯-4,6(5H)-二酮
• 中文别名: IN1618,1,3-二溴-5-(2-己基癸基)-4H-噻吩并[3,4-C]吡咯-4,6(5H)-二酮；1,3-二溴-5-(2-辛基十二烷基)-4H-噻吩并[3,4-C]吡咯-4,6(5H)-二酮
• 英文名称: 1,3-dibromo-5-(2-hexyldecyl)thieno[3,4-c]pyrrole-4,6-dione
• 英文别名: 1,3-dibromo-5-(2-hexyldecyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione
• CAS: 1234306-57-0
• 化学式: C₂₂H₃₃Br₂NO₂S
• 分子量: 535.384
• InChiKey: VYMBALVLRQSMNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  28
• 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

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  1,3-二溴-5-(2-己基癸基)-4H-噻吩并[3,4-C]吡咯-4,6(5H)-二酮 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-dodecyl)thien-2-yl]-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
• 作为产物：
  描述：

  2,5-二溴-噻吩-3,4-二羧酸 在 乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 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：

  适用于全聚合物本体异质结太阳能电池的Thieno [3,4-c]吡咯-4,6-二酮-3,4-二氟噻吩聚合物受体

  摘要：

  支链烷基取代的聚（噻吩并[3,4- c ^ ]吡咯-4,6- dione- ALT -3,4- difluorothiophene）（PTP-D [2F] T）可以用作在本体异质结的聚合物受体（BHJ ）具有低带隙聚合物供体（PCE10）的太阳能电池，通常与富勒烯一起使用。用PTPD [2F] T制造的“全聚合物” BHJ设备的效率高达4.4％。尽管迄今为止，最有效的聚合物受体是基于per二酰亚胺或萘二酰亚胺基序的，但我们对PTPD [2F] T聚合物的研究表明，具有充分取代的主链的线性全噻吩体系也可能有益于具有聚合物的高效BHJ太阳电池捐助者。

  DOI：

  10.1002/anie.201604307

文献信息

• 유기 반도체 화합물, 이의 제조방법 및 이를 포함하는 유기 전자 소자 및 유기 태양전지 소자
  申请人：Pusan National University Industry-University Cooperation Foundation 부산대학교 산학협력단(220040044843) BRN ▼621-82-06530

  公开号：KR20160004916A

  公开（公告）日：2016-01-13

  본 발명은 우수한 전기특성을 가지는 적층형 유기 태양전지의 유기반도체 화합물 그리고 단일층 유기 태양전지 소자에서 세계 최고 수준의 광-전 변환 효율을 나타내는 화합물, 이의 제조방법, 및 이를 함유하는 유기 전자 소자 및 유기 태양전지 소자에 관한 것으로, 본 발명의 유기반도체 화합물은 열적안정성, 용해도 및 전하이동도가 높아 이를 함유하는 적층형 유기 태양전지 소자에서 우수한 성능을 나타낸다.

  本发明涉及具有优异电特性的层叠型有机太阳能电池的有机半导体化合物，以及在世界最高水平的光-电转换效率的单层有机太阳能电池器件，其制造方法，以及包含该化合物的有机电子器件和有机太阳能电池器件。本发明的有机半导体化合物具有高的热稳定性、溶解度和电荷载流子迁移率，因此在包含该化合物的层叠型有机太阳能电池器件中表现出优异的性能。
• 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。
• Ternary Organic Solar Cells Based on Two Non‐fullerene Acceptors with Complimentary Absorption and Balanced Crystallinity
  作者：Lan Xie、Chen Yang、Ruimin Zhou、Zhen Wang、Jianqi Zhang、Kun Lu、Zhixiang Wei

  DOI：10.1002/cjoc.201900554

  日期：2020.9

  The ternary blend structure has been demonstrated as an effective approach to increase the power conversion efficiency of organic solar cells. An effective approach to enhance the power conversion efficiency of ternary solar cells is based on two non‐fullerene acceptors with complimentary absorption range and balanced crystallinity. In this work, we have introduced a high crystallinity small‐molecule

  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。
• SEMICONDUCTOR MATERIALS PREPARED FROM DITHIENYLVINYLENE COPOLYMERS
  申请人：Mishra Ashok Kumar

  公开号：US20120217482A1

  公开（公告）日：2012-08-30

  Disclosed are new semiconductor materials prepared from dithienylvinylene copolymers with aromatic or heteroaromatic π-conjugated systems. Such copolymers, with little or no post-deposition heat treatment, can exhibit high charge carrier mobility and/or good current modulation characteristics. In addition, the polymers of the present teachings can possess certain processing advantages such as improved solution-processability and low annealing temperature.

  本发明揭示了由含芳香或杂芳香π-共轭系统的二噻吩乙烯共聚物制备的新型半导体材料。这种共聚物在很少或没有沉积后热处理的情况下，可以表现出高载流子迁移率和/或良好的电流调制特性。此外，本发明所述的聚合物还具有某些加工优点，如改善的溶液加工性和低退火温度。
• 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。