5,5'-二溴-3,3'-二氟-2,2'-联噻吩 | 1619967-08-6

• 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
• 中文名称: 5,5'-二溴-3,3'-二氟-2,2'-联噻吩
• 英文名称: 5,5'-dibromo-3,3'-difluoro-2,2'-bithiophene
• 英文别名: 5-bromo-2-(5-bromo-3-fluorothiophen-2-yl)-3-fluorothiophene
• CAS: 1619967-08-6
• 化学式: C₈H₂Br₂F₂S₂
• 分子量: 360.041
• InChiKey: FEFQRVDSNOVCNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis(4-(methylthio)phenyl)amine 、 5,5'-二溴-3,3'-二氟-2,2'-联噻吩 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium t-butanolate 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以70.5%的产率得到3,3'-difluoro-N5,N5,N5',N5'-tetra(4-(methylthio)phenyl)-[2,2'-bithiophene]-5,5'-diamine
  参考文献：
  名称：

  基于双氟连噻吩单元的有机分子及其作为空穴传输材料在钙钛矿太阳能电池中的应用

  摘要：

  本发明属于有机功能材料技术领域，本发明公开了基于双氟连噻吩单元的有机分子及其作为空穴传输材料在钙钛矿太阳能电池中的应用，选取3‑氟噻吩单元作为中心基元，构建具有电子给体单元(D)‑平面氟代π桥‑电子给体单元(D)的分子空穴传输材料。具体合成出3,3'‑二氟‑[2,2'‑连噻吩]两端对称性连接双(4‑(甲硫基)二苯)胺和双(4‑(甲硫基)三苯)胺的有机分子材料(DFBT‑DPA‑MT和DFBT‑TPA‑MT)，并将两种材料作为空穴传输层在平面钙钛矿太阳能电池中进行应用。基于DFBT‑DPA‑MT和DFBT‑TPA‑MT作为空穴传输层的平面钙钛矿太阳能电池，能量转换效率分别可以超过19％。

  公开号：

  CN111875579A
• 作为产物：
  描述：

  2-溴-4-氟噻吩 在 1,10-邻二氮杂菲-5,6-二酮 、 氧气 、 palladium diacetate 、 copper(II) acetate monohydrate 、 对苯醌 作用下， 以 二甲基亚砜 为溶剂， 120.0 ℃ 、111.46 kPa 条件下， 反应 16.0h， 以73%的产率得到5,5'-二溴-3,3'-二氟-2,2'-联噻吩
  参考文献：
  名称：

  Pd催化噻吩的好氧氧化偶联：菲咯啉二酮和铜助催化剂的协同作用

  摘要：

  取代的联噻吩是功能性有机材料中的重要片段，它们理想地通过直接氧化 CH/CH 偶联制备。在这里，我们报告了一种新型 PdII 催化剂体系，采用 1,10-phenanthroline-5,6-dione (phd) 作为辅助配体，能够实现 2-溴噻吩和其他相关杂环的有氧氧化同系偶联。这些观察结果代表了首次使用 phd 来支持 Pd 催化的有氧氧化。该反应还得益于 Cu(OAc)2 助催化剂，机理研究表明，Cu 促进了 CC 偶联，这表明 CuII 的作用不同于其对 Pd 催化剂再氧化的传统贡献。

  DOI：

  10.1021/jacs.0c09962

文献信息

• Method for Aerobic Oxidative Coupling of Thiophenes with a Ligand-Supported Palladium Catalyst
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20190210993A1

  公开（公告）日：2019-07-11

  An oxidative homocoupling method of synthesizing certain 2,2′-bithiophenes from thiophenes using oxygen as the terminal oxidant is disclosed. In non-limiting examples, the method uses oxygen along with a catalytic system that includes palladium, an assistive ligand, and a non-palladium metal additive to catalyze one of the following reactions: Associated catalytic systems and compositions are also disclosed.

  披露了一种利用氧气作为末端氧化剂，从噻吩合成特定的2,2′-双噻吩的氧化性自偶联方法。在非限制性的示例中，该方法使用氧气以及包括钯、辅助配体和非钯金属添加剂的催化系统来催化以下反应之一：同时还披露了相关的催化系统和组合物。
• Oligothiophene-based small molecules with 3,3′-difluoro-2,2′-bithiophene central unit for solution-processed organic solar cells
  作者：Bin Kan、Qian Zhang、Xiangjian Wan、Xin Ke、Yunchuang Wang、Huanran Feng、Mingtao Zhang、Yongsheng Chen

  DOI：10.1016/j.orgel.2016.08.014

  日期：2016.11

  Two new oligothiophene-based small molecules, namely DRCN6T-F and DRCN8T-F, with 3,3′-difluoro-2,2′-bithiophene as the central building block and 2-(1,1-dicyanomethylene)-rhodanine as end groups, were designed and synthesized. Compared to their non-fluorinated counterparts DRCN6T and DRCN8T, DRCN6T-F and DRCN8T-F exhibit enhanced intermolecular interactions and lower HOMO energy levels. However, PCEs

  两个新的基于寡聚噻吩的小分子，即DRCN6T-F和DRCN8T-F，以3,3'-二氟-2,2'-联噻吩为中心结构单元，以2-（1,1-二氰基亚甲基）-罗丹宁为末端设计并合成了两个组。与它们的非氟化对应物DRCN6T和DRCN8T相比，DRCN6T-F和DRCN8T-F表现出增强的分子间相互作用和较低的HOMO能级。但是，基于DRCN6T-F和DRCN8T-F的优化器件的PCE分别为2.26％和5.07％，低于非氟化分子DRCN6T和DRCN8T的PCE。。DRCN6T-F和DRCN8T-F相对较差的性能主要是由于其不良的形态和低的载流子迁移率而导致的短路电流密度低。
• Tetra-aryl indacenodithiophene-based polycyclic polymers and their use
  申请人：Merck Patent GmbH

  公开号：US10270034B2

  公开（公告）日：2019-04-23

  The present invention relates to compounds comprising a tetra-aryl indacenodithiophene-based structural unit, the synthesis of such compounds as well as their use in organic electronic devices. The invention further relates to organic electronic devices comprising such compounds.

  本发明涉及包含四芳基茚并噻吩结构单元的化合物、此类化合物的合成及其在有机电子器件中的应用。本发明还涉及包含此类化合物的有机电子器件。
• Method for aerobic oxidative coupling of thiophenes with a ligand-supported palladium catalyst
  申请人：Wisconsin Alumni Research Foundation

  公开号：US10858334B2

  公开（公告）日：2020-12-08

  An oxidative homocoupling method of synthesizing certain 2,2′-bithiophenes from thiophenes using oxygen as the terminal oxidant is disclosed. In non-limiting examples, the method uses oxygen along with a catalytic system that includes palladium, an assistive ligand, and a non-palladium metal additive to catalyze one of the following reactions: Associated catalytic systems and compositions are also disclosed.

  本发明公开了一种以氧为末端氧化剂从噻吩合成某些2,2′-噻吩的氧化均偶联方法。在非限制性实例中，该方法使用氧气和包括钯、辅助配体和非钯金属添加剂的催化体系来催化下列反应之一： 还公开了相关的催化体系和组合物。
• Implication of Fluorine Atom on Electronic Properties, Ordering Structures, and Photovoltaic Performance in Naphthobisthiadiazole-Based Semiconducting Polymers
  作者：Kazuaki Kawashima、Tomohiro Fukuhara、Yousuke Suda、Yasuhito Suzuki、Tomoyuki Koganezawa、Hiroyuki Yoshida、Hideo Ohkita、Itaru Osaka、Kazuo Takimiya

  DOI：10.1021/jacs.6b05418

  日期：2016.8.17

  The development of semiconducting polymers is imperative to improve the performance of polymer-based solar cells (PSCs). In this study, new semiconducting polymers based on naphtho[1,2-c:5,6-c']bis[1,2,5]thiadiazole (NTz), PNTz4TF2 and PNTz4TF4, having 3,3'-difluoro-2,2'-bithiophene and 3,3',4,4'-tetrafluoro-2,2'-bithiophene, respectively, are designed and synthesized. These polymers possess a deeper HOMO energy level than their counterpart, PNTz4T, which results in higher open-circuit voltages in solar cells. This concequently reduces the photon energy loss that is one of the most important issues surrounding PSCs. The PNTz4TF4 cell exhibits up to 6.5% power conversion efficiency (PCE), whereas the PNTz4TF2 cell demonstrates outstanding device performance with as high as 10.5% PCE, which is quite high for PSCs. We further discuss the performances of the PSCs based on these polymers by correlating the charge generation and recombination dynamics with the polymer structure and ordering structure. We believe that the results provide new insights into the design of semiconducting polymers and that there is still much room for improvement of PSC efficiency.