4,7-di(thiophen-2-yl)benzo[c][1,2,5]oxadiazole | 1033235-00-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: 4,7-di(thiophen-2-yl)benzo[c][1,2,5]oxadiazole
• 英文别名: 4,7-dithiophen-2-yl-2,1,3-benzoxadiazole
• CAS: 1033235-00-5
• 化学式: C₁₄H₈N₂OS₂
• 分子量: 284.362
• InChiKey: WYJDLCCBMIGQDL-UHFFFAOYSA-N

物化性质

• 沸点：
  471.4±55.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,7-di(thiophen-2-yl)benzo[c][1,2,5]oxadiazole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 邻二氯苯 为溶剂， 生成 2,1,3-苯并恶二唑,4,7-双(5-溴-2-噻吩)-
  参考文献：
  名称：

  D?A?D low band gap molecule containing triphenylamine and benzoxadiazole/benzothiadiazole units: Synthesis and photophysical properties

  摘要：

  Two D-A-D-type low band gap organic dyes based on triphenylamine and benzoxadiazole/benzothiadiazole, 4,7-Bis{5-{4-{2-[4-(N,N-diphenylamino)phenyl]-1-nitrilethenyl}phenyl}-2-thienyl}-2,1,3-benzoxadiazole (BDNTBX) and 4,7-Bis{5-{4-{2-[4-(N,N-diphenylamino)phenyl]-1-nitrilethenyl}phenyl}-2-thienyl}-2,1,3-benzothiadiazole (BDNTBT) were successfully synthesized. The properties of two compounds were investigated by density functional theory (DFT) calculations, UV-vis absorption spectroscopy, cyclic voltammetry and fluorescence quenching experiment. The calculated ground-state geometries demonstrate intramolecular charge transfer (ICE) occurs in both molecules during the procedure of charge excitation from HOMO to LUMO. From the data in electrochemistry and fluorescence quenching experiments, the molecules reveal lower HOMO energy levels compared with that of P3HT and proper LUMO energy levels to obtain efficient charge separation with PCBM. Two synthesized compounds exhibit broad absorption range covering the whole visible spectral region. These photophysical and electrochemical properties call attention to that our materials are prospective candidates as donor materials for solution-processable organic photovoltaic cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.04.001
• 作为产物：
  描述：

  甲基硝基苯 在 吗啉 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium hypochlorite 、 四丁基溴化铵 、 溴 、 铁粉 、 sulfur 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 乙二醇 为溶剂， 生成 4,7-di(thiophen-2-yl)benzo[c][1,2,5]oxadiazole
  参考文献：
  名称：

  D?A?D low band gap molecule containing triphenylamine and benzoxadiazole/benzothiadiazole units: Synthesis and photophysical properties

  摘要：

  Two D-A-D-type low band gap organic dyes based on triphenylamine and benzoxadiazole/benzothiadiazole, 4,7-Bis{5-{4-{2-[4-(N,N-diphenylamino)phenyl]-1-nitrilethenyl}phenyl}-2-thienyl}-2,1,3-benzoxadiazole (BDNTBX) and 4,7-Bis{5-{4-{2-[4-(N,N-diphenylamino)phenyl]-1-nitrilethenyl}phenyl}-2-thienyl}-2,1,3-benzothiadiazole (BDNTBT) were successfully synthesized. The properties of two compounds were investigated by density functional theory (DFT) calculations, UV-vis absorption spectroscopy, cyclic voltammetry and fluorescence quenching experiment. The calculated ground-state geometries demonstrate intramolecular charge transfer (ICE) occurs in both molecules during the procedure of charge excitation from HOMO to LUMO. From the data in electrochemistry and fluorescence quenching experiments, the molecules reveal lower HOMO energy levels compared with that of P3HT and proper LUMO energy levels to obtain efficient charge separation with PCBM. Two synthesized compounds exhibit broad absorption range covering the whole visible spectral region. These photophysical and electrochemical properties call attention to that our materials are prospective candidates as donor materials for solution-processable organic photovoltaic cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.04.001

文献信息

• Structural Design Principle of Small-Molecule Organic Semiconductors for Metal-Free, Visible-Light-Promoted Photocatalysis
  作者：Lei Wang、Wei Huang、Run Li、Dominik Gehrig、Paul W. M. Blom、Katharina Landfester、Kai A. I. Zhang

  DOI：10.1002/anie.201603789

  日期：2016.8.8

  on the structural design principle of small‐molecule organic semiconductors as metal‐free, pure organic and visible light‐active photocatalysts. Two series of electron‐donor and acceptor‐type organic semiconductor molecules were synthesized to meet crucial requirements, such as 1) absorption range in the visible region, 2) sufficient photoredox potential, and 3) long lifetime of photogenerated excitons

  在此，我们报告了小分子有机半导体作为无金属，纯有机和可见光活性光催化剂的结构设计原理。合成了两个系列的电子给体和受体型有机半导体分子以满足关键要求，例如1）可见光区域的吸收范围，2）足够的光氧化还原电势和3）光生激子的寿命长。在富含丙二酸酯衍生物的富电子杂芳族化合物的分子间CH官能化中证明了光催化活性。描述了光诱导电子在有机光催化剂，底物和牺牲剂之间传输的机理。凭借其可调的吸收范围和定义的能带结构，
• Effects of including electron-withdrawing atoms on the physical and photovoltaic properties of indacenodithieno[3,2-b]thiophene-based donor–acceptor polymers: towards an acceptor design for efficient polymer solar cells
  作者：Ping Cai、Xiaofeng Xu、Jiangman Sun、Junwu Chen、Yong Cao

  DOI：10.1039/c7ra01049d

  日期：——

  Three new D–A polymers using indacenodithieno[3,2-b]thiophene (IDTT) as an electron-rich unit and benzoxadiazole (BO), benzodiathiazole (BT) or difluorobenzothiadiazole (FBT) as an electron-deficient unit were synthesized and applied in solar cells.

  以茚并二噻吩并[3,2-b]噻吩（IDTT）为富电子单元，苯并噁二唑（BO）、苯并二噻唑（BT）或二氟苯并噻二唑（FBT）为缺电子单元，合成了三种新型 D-A 聚合物，并将其应用于太阳能电池。
• Benzochalcogendiazole-based conjugated molecules: investigating the effects of substituents and heteroatom juggling
  作者：Heta A. Patel、Viraj J. Bhanvadia、Hemant M. Mande、Sanjio S. Zade、Arun L. Patel

  DOI：10.1039/c9ob01762c

  日期：——

  photophysical properties of the synthesized benzochalcogendiazole-based small molecules, having different terminal substituents, have been compared. Moreover, the structural aspects, including the packing patterns and non-bonding interactions of the conjugated molecules, have been investigated using the single crystal X-ray diffraction (SCXRD) technique.

  使用聚苯胺（PANI）固定的钯作为非均相催化剂，已经获得了一种方便有效的基于苯并硫属元素二唑的小分子合成方法。已经比较了具有不同末端取代基的合成的苯并硫属元素二唑基小分子的光物理性质。此外，已经使用单晶X射线衍射（SCXRD）技术研究了包括共轭分子的堆积模式和非键相互作用在内的结构方面。
• Synthesis, photophysical, electrochemical and single-crystal x-ray diffraction study of (<i>Z</i>)-2-phenyl-3-(5-(4-(thiophen-2-yl)benzo[c][1,2,5]thiadiazol-7-yl)thiophen-2-yl)acrylonitrile
  作者：Viraj J. Bhanvadia、Heta A. Patel、Neha N. Sharma、Arun L. Patel

  DOI：10.1080/00397911.2016.1185125

  日期：2016.6.17

  properties, thermogravimetric stability and single-crystal X-ray diffraction study of (Z)-2-phenyl-3-(5-(4-(thiophen-2-yl)benzo[c][1,2,5]thiadiazol-7-yl)thiophen-2-yl)acrylonitrile are examined using ultraviolet–visible spectrophotometry, cyclic voltammetry, thermal gravimetric analysis–diffraction scanning calorimetry analysis, single-crystal X-ray diffraction and density functional theory calculations

  摘要 (Z)-2-苯基-3-(5-(4-(噻吩-2-基)苯并[c][1, 2,5]噻二唑-7-基)噻吩-2-基)丙烯腈使用紫外-可见分光光度法、循环伏安法、热重分析-衍射扫描量热分析、单晶X射线衍射和密度泛函理论计算进行检测。显然，化合物 6 的晶体结构是由许多弱的非常规分子间吸引力维持的，例如 CH ... N、CH ... π 供体 - 受体相互作用。图形概要
• POLYMERS OF 8,9-DIHYDROBENZO[DEF]CARBAZOLE AND THEIR USE AS ORGANIC SEMICONDUCTORS
  申请人：Blouin Nicolas

  公开号：US20130001476A1

  公开（公告）日：2013-01-03

  The invention relates to novel polymers containing 8,9-dihydrobenzo[def]carbazole units, methods and materials for their preparation, their use as semiconductors in organic electronic (OE) devices, and to OE devices comprising these polymers.

  该发明涉及含有8,9-二氢苯并[def]咔唑单元的新型聚合物，以及它们的制备方法和材料，它们作为有机电子（OE）器件中的半导体的用途，以及包含这些聚合物的OE器件。