2,6-二苯基二噻吩[3,2-B:2',3'-D]噻吩 | 881838-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻吩类
• 中文名称: 2,6-二苯基二噻吩[3,2-B:2',3'-D]噻吩
• 英文名称: 2,6-diphenyldithieno[3,2-b:2′,3′-d]thiophene
• 英文别名: DP-DTT；2,6-Diphenyldithieno[3,2-b:2',3'-d]thiophene；4,10-diphenyl-3,7,11-trithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene
• CAS: 881838-94-4
• 化学式: C₂₀H₁₂S₃
• 分子量: 348.513
• InChiKey: DHVHYUGTODNKLB-UHFFFAOYSA-N

物化性质

• 沸点：
  565.3±45.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为产物：
  描述：

  溴苯 、 二噻吩[3,2-B:2',3'-D]噻吩 在 正丁基锂 、 三丁基氯化锡 、 四(三苯基膦)钯 作用下， 以 乙醚 、 Petroleum ether 、 甲苯 为溶剂， 反应 25.0h， 以50%的产率得到2,6-二苯基二噻吩[3,2-B:2',3'-D]噻吩
  参考文献：
  名称：

  Functionalized dithieno[2,3-b:3′,2′-d]thiophenes (DTTs) for organic thin-film transistors

  摘要：

  A series of dithieno[2,3-b:3',2'-d]thiophene (DTT;1) derivatives were synthesized and characterized. Facile, one-pot [2 + 1] and [1 + 1 + 1] synthetic methods of DTT were developed, which enabled the efficient realization of a new DTT-based semiconductor series for organic thin-film transistors (OTFTs). These DTTs are end-functionalized with perfluorophenyl (FP-), perfluorobenzoyl (FB-), benzoyl (B-), 2-naphthylcarbonyl (Np-), 2-benzothiazolyl (BS-), 2-thienylcarbonyl (T-), and 2-(5-hexyl)thienylcarbonyl (HT-) groups. The molecular structures of DFP-DTT (3), DFB-DTT (4), FBB-DTT (5), DB-DTT (6), and DNp-TT (7) were determined via single-crystal X-ray diffraction. Our studies reveal that the majority of these carbonyl-containing derivatives exhibit p-channel transport with hole mobilities of up to 0.01 cm(2)/Vs for DB-DTT and DBS-DTT, while perfluorobenzoyl and perfluorophenyl-substituted compounds exhibit n-channel transport with mobilities up to 0.002 cm(2)/Vs for DFB-DTT, 0.03 cm(2)/Vs for FBB-DTT, and 0.07 cm(2)/Vs for DFP-DTT, rendering the latter the DTT derivative currently having the highest electron mobility in OTFT devices. Within this family, the carrier mobility values are strongly dependent upon the semiconductor growth temperature and the dielectric surface treatment. (C) 2010 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.orgel.2010.01.022

文献信息

• Improvement of the redox stability of dithieno[3,2-b:2′,3′-d]thiophene derivatives by using bulky substituents
  作者：Shinjiro Okada、Kenji Yamada

  DOI：10.1016/j.molstruc.2013.01.002

  日期：2013.4

  redox stability of dithieno[3,2-b:2′,3′-d]thiophene (DTT), we synthesized derivatives with differently sized substituents. It is well known that substituents in the 2, 6 positions of DTT are active in this respect. We provide in this article more insight into mechanism. The present study provides the first support for a size effect. Large size substituents in the 2, 6 positions of the DTT are more effective

  摘要 为了提高二噻吩并 [3,2-b:2',3'-d] 噻吩 (DTT) 的长期氧化还原稳定性，我们合成了具有不同大小取代基的衍生物。众所周知，DTT 2、6 位的取代基在这方面是有活性的。我们在本文中提供了对机制的更多见解。本研究为规模效应提供了第一个支持。DTT 2、6 位的大尺寸取代基比小尺寸取代基更有效。在这些化合物中，DTT 充当 HOMO 所在分子的核心，而取代基充当笼子以保护核心免受来自外部的各种攻击。这种核心笼系统不仅可以有效防止聚合，而且还可以提高长期氧化还原稳定性。具有大尺寸取代基的化合物，如 (1,1':3', 1″-三联苯)-2-基和4,4'-二-叔丁基-(1,1'-联苯)-2-基表现出优异的长期氧化还原稳定性。氧化电位在分别高达 17,000 次和 20,000 次的重复氧化过程中保持不变。具有小尺寸取代基的化合物，如苯基和甲基，显示出该耐久性的 1/10 或更少
• PHOTOELECTRIC CONVERSION ELEMENT AND IMAGING DEVICE
  申请人：Sony Corporation

  公开号：EP3686944A1

  公开（公告）日：2020-07-29

  [Problem] Provided are a photoelectric conversion device and an imaging apparatus capable of improving quantum efficiency and a response speed. [Solving means] A first photoelectric conversion device according to one embodiment of the present disclosure includes a first electrode, a second electrode opposed to the first electrode, and a photoelectric conversion layer. The photoelectric conversion layer is provided between the first electrode and the second electrode and includes at least one type of one organic semiconductor material having crystallinity. Variation in a ratio between horizontally-oriented crystal and vertically-oriented crystal in the photoelectric conversion layer is three times or less between a case where film formation of the one organic semiconductor material is performed at a first temperature and a case where the film formation of the one organic semiconductor material is performed at a second temperature. The second temperature is higher than the first temperature.

  [问题]提供了一种能够提高量子效率和响应速度的光电转换装置和成像设备。 [解决方法]根据本公开的一个实施例，第一光电转换器件包括第一电极、与第一电极相对的第二电极和光电转换层。光电转换层设置在第一电极和第二电极之间，包括至少一种具有结晶性的有机半导体材料。光电转换层中水平方向晶体和垂直方向晶体的比例变化在第一温度下有机半导体材料成膜和第二温度下有机半导体材料成膜的情况之间为三倍或更小。第二温度高于第一温度。
• Photoelectric conversion device and imaging apparatus
  申请人：Sony Corporation

  公开号：US11538863B2

  公开（公告）日：2022-12-27

  [Problem] Provided are a photoelectric conversion device and an imaging apparatus capable of improving quantum efficiency and a response speed. [Solving means] A first photoelectric conversion device according to one embodiment of the present disclosure includes a first electrode, a second electrode opposed to the first electrode, and a photoelectric conversion layer. The photoelectric conversion layer is provided between the first electrode and the second electrode and includes at least one type of one organic semiconductor material having crystallinity. Variation in a ratio between horizontally-oriented crystal and vertically-oriented crystal in the photoelectric conversion layer is three times or less between a case where film formation of the one organic semiconductor material is performed at a first temperature and a case where the film formation of the one organic semiconductor material is performed at a second temperature. The second temperature is higher than the first temperature.

  [问题]提供了一种能够提高量子效率和响应速度的光电转换装置和成像设备。 [解决方法]根据本公开的一个实施例，第一光电转换器件包括第一电极、与第一电极相对的第二电极和光电转换层。光电转换层设置在第一电极和第二电极之间，包括至少一种具有结晶性的有机半导体材料。光电转换层中水平方向晶体和垂直方向晶体的比例变化在第一温度下有机半导体材料成膜和第二温度下有机半导体材料成膜的情况之间为三倍或更小。第二温度高于第一温度。
• ELECTROCHROMIC ELEMENT
  申请人：Canon Kabushiki Kaisha

  公开号：EP2719702B1

  公开（公告）日：2016-05-11
• ORGANIC COMPOUND AND ELECTROCHROMIC DEVICE INCLUDING THE SAME
  申请人：Canon Kabushiki Kaisha

  公开号：EP2588484B1

  公开（公告）日：2015-11-04