4,7-bis(5-bromo-3-octylthiophen-2-yl)-2,1,3-benzothiadiazole | 1207196-62-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: 4,7-bis(5-bromo-3-octylthiophen-2-yl)-2,1,3-benzothiadiazole
• 英文别名: 4,7-bis(5-bromo-3-Octyl-2-thienyl)-2,1,3-benzothiadiazole；4,7-Bis(5-bromo-3-octylthiophen-2-yl)benzo[c][1,2,5]thiadiazole
• CAS: 1207196-62-0
• 化学式: C₃₀H₃₈Br₂N₂S₃
• 分子量: 682.651
• InChiKey: ZVHUUQVETAZCBC-UHFFFAOYSA-N

物化性质

• 沸点：
  684.3±55.0 °C(Predicted)
• 密度：
  1.351±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,7-bis(5-bromo-3-octylthiophen-2-yl)-2,1,3-benzothiadiazole 在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 40.0h， 生成 4,7-Bis[5-(5-bromo-3-octylthiophen-2-yl)-3-octylthiophen-2-yl]-2,1,3-benzothiadiazole
  参考文献：
  名称：

  Photoelectric materials and preparation thereof

  摘要：

  受体型寡硫代噻吩化合物，制备这些化合物的方法，以及在光电材料中使用这些化合物的方法。

  公开号：

  US09184315B2
• 作为产物：
  描述：

  2,1,3-苯并噻二唑 在 N-溴代丁二酰亚胺(NBS) 、 氢溴酸 、 溴 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 4,7-bis(5-bromo-3-octylthiophen-2-yl)-2,1,3-benzothiadiazole
  参考文献：
  名称：

  Synthesis of N-[4-Octylphenyl]dithieno[3,2-b:2′,3′-d]pyrrole-based broad absorbing polymers and their photovoltaic applications

  摘要：

  Electron rich, fused N-aryl pyrrole based monomer namely 2,6-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolan)-N-[4-octylphenyl]dithieno[3,2-b:2',3'-d]pyrrole (N-aryl DTP) was synthesized and copolymerized with electron deficient 4,7-bis(5-bromo-3-octyl-2-thienyl)-2,1,3-benzothiadiazole (TBT) to afford alternating polymer PDTPTBT. The absorption band of PDTPTBT was found to cover the entire visible part of the solar spectrum (300 nm-750 nm) and the optical band gap was estimated to be 1.62 eV. In order to extent the absorption of PDTPTBT, another strong electron acceptor unit such as 2,1,3-benzothiadiazole or dimethyl-2H-benzimidazole was incorporated in polymer main chain by copolymerizing three different comonomers (N-aryl DTP, TBT and 4,7-dibromo-2,1,3-benzothiadiazole (B) or 4,7-dibromo-2,2-dimethyl-2H-benzimidazole (BI)) at 2:1:1 ratio to afford polymers PDTPTBTB and PDTPTBTBI, respectively. The absorption band of PDTPTBTB and PDTPTBTBI was found to be extended up to 1000 nm and 1200 nm, respectively, and the optical band gap was calculated to be 1.33 eV and 1.07 eV, respectively. The HOMO-LUMO energy levels of PDTPTBT, PDTPTBTB and PDTPTBTBI were found to be suitable for polymer solar cell (PSC) applications. The single layer PSCs fabricated with the configuration of ITO/PEDOT:PSS/PDTPTBT, PDTPTBTB or PDTPTBTBI:PC60BM(1:3 wt/wt)/LiF/Al showed maximum power conversion efficiency (PCE) of 2.04%, 1.01% and 0.70%, respectively. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2013.04.049

文献信息

• Energy transfer along a sequence controlled hybrid polymer
  作者：Xiaoxiao Zhang、Hong Chi、Tianduo Li、FuKe Wang、Wee Shong Chin、Jing Xu

  DOI：10.1002/pola.29002

  日期：2018.6.15

  polymer chain. The dynamics of energy transfer in poly(fluorene‐POSS‐alt‐POSS‐benzothiodiazole) (PTBtTbOFl3) is studied by steady state as well as time resolved fluorescence spectroscopy at different donor/acceptor ratios. Results reveal that POSS can effectively shield inter‐chains energy transfer of the polymers, suggesting it is an effective model for energy transfer study with less inter‐chains effects

  通过使用大体积的多面体低聚倍半硅氧烷（POSS）来屏蔽聚合物主链，目前的工作为共轭聚合物的链内能量转移研究提供了理想模型。POSS为聚合物主链提供周向屏蔽，以防止聚合物链的紧密堆积，从而使链内能量转移在较大浓度范围内占主导地位。双功能POSS（B-POSS）专门设计用于在聚合物链中分离供体（芴）和受体（苯并噻二唑）。能量传递的在聚（芴POSS-动力学ALT -POSS-benzothiodiazole）（PTBtTbOFl 3通过稳态以及在不同供体/受体比率下的时间分辨荧光光谱法研究）。结果表明，POSS可以有效地屏蔽聚合物的链间能量转移，这表明它是进行链间影响较小的能量转移研究的有效模型。PTBtTbOFl 3用作化学传感器，在爆炸性衍生物的检测中也有报道。这些结果为优化用于光电器件的纳米结构材料提供了见识。©2018 Wiley Periodicals，Inc.J.Polym。科学，A部分：Polym。化学
• Synthesis of conjugated polymers with broad absorption bands and photovoltaic properties as bulk heterojuction solar cells
  作者：Vellaiappillai Tamilavan、Myungkwan Song、Sung-Ho Jin、Myung Ho Hyun

  DOI：10.1016/j.polymer.2011.03.040

  日期：2011.5

  832 nm in film. The electrochemical band gaps of the polymers were calculated to be 1.88 eV and 1.87 eV, respectively, while the optical band gaps of the polymers were calculated to be 1.94 eV and 1.87 eV, respectively. The photovoltaic properties of polymers were investigated with bulk heterojunction (BHJ) solar cells fabricated in ITO/PEDOT:PSS/polymer:PC70BM(1:5 wt%)/TiOx/Al configurations. The maximum

  两个新的宽吸收交替共聚物，聚[1-（2,6-二异丙基苯基）-2,5-双（2-噻吩基）吡咯ALT -4,7-双（3-辛基-噻吩基）苯并噻二唑（PTPTTBT - P1）和聚[1-（p辛基苯基）-2,5-双（2-噻吩基）吡咯ALT -4,7-双（3-辛基-噻吩基）苯并噻二唑（PTPTTBT - P2）通过Suzuki缩聚反应以高收率制备。发现这两种聚合物在太阳光谱的可见光区域显示出特征吸收。有趣的是PTPTTBT - P1的吸收发现膜中可见光区域覆盖了350至650 nm，最大和平坦吸收范围为440 nm至510 nm，而PTPTTBT - P2的吸收率覆盖了350至950 nm可见区域，且吸收率相对不同薄膜在425和522 nm处有最大吸收，在832 nm处有非常弱的吸收最大值。聚合物的电化学带隙经计算分别为1.88eV和1.87eV，而聚合物的光学带隙经计算分别为1.94eV和1.87eV。使用在ITO
• PHOTOELECTRIC MATERIALS AND PREPARATION THEREOF
  申请人：Chen Yongsheng

  公开号：US20140142308A1

  公开（公告）日：2014-05-22

  Receptor type oligothiopene compounds, methods of preparing the compounds, and use of the compounds in photoelectric materials.

  受体型寡硫杂苯化合物，制备该化合物的方法，以及在光电材料中使用该化合物的方法。
• Donor−Acceptor Polymers Incorporating Alkylated Dithienylbenzothiadiazole for Bulk Heterojunction Solar Cells: Pronounced Effect of Positioning Alkyl Chains
  作者：Huaxing Zhou、Liqiang Yang、Shengqiang Xiao、Shubin Liu、Wei You

  DOI：10.1021/ma902241b

  日期：2010.1.26

  4,7-Di(thiophen-2-yl)benzothiadiazole (DTBT) has been used to construct a number of donor-acceptor low band gap polymers for bulk heterojunction (BHJ) photovoltaics with high efficiency numbers. Its strong tendency to pi-stack often leads to polymers with low molecular weight and poor solubility, which could potentially be alleviated by anchoring solubilizing chains onto the DTBT unit. A systematic study of the effect of positioning alkyl chains on DTBT on properties of polymers was implemented by investigating a small library of structurally related polymers with identical Conjugated backbone. This series of donor-acceptor polymers employed a common donor unit, benzo[2,1-b:3,4-b']dithiophene (BDT). and modified DTBT as the acceptor unit. Three variations of modified DTBT units Were prepared with alkyl side chains at (a) the 5- and 6-positions of 2,1,3-benzothiadiazole (DTsolBT), (b) 3-positions of the flanking thienyl groups (3DTBT), and (c) 4-positions (4DTBT), in addition to the unmodified DTBT. Contrary to results from previous studies, optical and electrochemical studies disclosed almost identical band gap and energy levels between PBDT-4DTBT and PBDT-DTBT. These results indicated that anchoring solubilizing alkyl chains on the 4-positions of DTBT only introduced a minimum steric hindrance within BDT-DTBT maintaining the extended conjugation of the fundamental structural unit (BDT-DTBT). More importantly, the additional high molecular weight and excellent solubility of PBDT-4DTBT led to a more uniform mixture with PCBM, with better control on the film morphology. All these features of PBDT-4DTBT led to a significantly improved efficiency of related BHJ solar cells (up to 2.2% has beep, observed), triple the efficiency obtained from BHJ devices fabricated from the "conventional" PBDT-DTBT (0.72%). Our discovery reinforced the importance of high molecular weight and good solubility of donor polymers for BHJ solar cells, in addition to a low band gap and a low HOMO energy level, in order to further enhance the device efficiencies.
• US9184315B2
  申请人：——

  公开号：US9184315B2

  公开（公告）日：2015-11-10