(E)-4-(5-(2-(2,5-dibromothiophen-3-yl)vinyl)thiophen-2-yl)-N,N-diphenylaniline | 1275591-14-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-4-(5-(2-(2,5-dibromothiophen-3-yl)vinyl)thiophen-2-yl)-N,N-diphenylaniline
• 英文别名: MTD；4-[5-[(E)-2-(2,5-dibromothiophen-3-yl)ethenyl]thiophen-2-yl]-N,N-diphenylaniline
• CAS: 1275591-14-4
• 化学式: C₂₈H₁₉Br₂NS₂
• 分子量: 593.406
• InChiKey: ORDRCSKTJGXLQM-DTQAZKPQSA-N

物化性质

• 沸点：
  661.9±55.0 °C(predicted)
• 密度：
  1.559±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-溴三苯胺 在 四(三苯基膦)钯 、 正丁基锂 、 sodium methylate 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 16.0h， 生成 (E)-4-(5-(2-(2,5-dibromothiophen-3-yl)vinyl)thiophen-2-yl)-N,N-diphenylaniline
  参考文献：
  名称：

  Bulky side-chain density effect on the photophysical, electrochemical and photovoltaic properties of polythiophene derivatives

  摘要：

  Low band-gap polythiophene (PT) derivatives, with bulky conjugated side-chains composed of the triphenylamine, thiophene, and vinylene groups (TPATh), are synthesized. The copolymers, synthesized by Grignard metathesis and Stille coupling with different copolymer configurations and side-chain densities, are regioregular-TPATh-PT (rr-TPATh-PT) and random-TPATh-PT (r-TPATh-PT), respectively. The incorporation of bulky conjugated moiety curtails the effective conjugation length in the main chain; thus, low HOMO levels are obtained for the copolymers. Moreover, r-TPATh-PT with less bulky side-chain content exhibits a better conjugation along the polymer backbone than rr-TPATh-PT. Higher absorption intensity in the vision region is observed for r-TPATh-PT in comparison with rr-TPATh-PT. In addition, polymer solar cells (PSCs) are fabricated based on an interpenetrating network of PT derivatives as the electron donor and the fullerene derivatives (PC61BM and PC71BM) as the electron acceptors. Better compatibility is observed for the r-TPATh-PT/PC61BM-blend film as compared to the rr-TPATh-PT/PC61BM-blend film. Higher photovoltaic (PV) performances of the r-TPATh-PT/PC61BM-based PSCs are observed in comparison with the rr-TPATh-PT/PC61BM-based PSCs. The power conversion efficiency (PCE) of the PSC based on the blend of r-TPATh-PT and PC61BM (w/w = 1:1) reaches 0.94% under an illumination of AM 1.5G, 100 mW cm(-2), which is almost twice that of the cell based on rr-TPATh-PT. Further improvement of PV performance is achieved for the PSC fabricated from the blend of r-TPATh-PT and fullerene derivative PC71BM (w/w = 1:3), with a short-circuit current of 6.83 mA cm(-2), an open-circuit voltage of 0.71 V and a PCE of 1.75%. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2010.11.036

文献信息

• Effect of side chain conjugation lengths on photovoltaic performance of two-dimensional conjugated copolymers that contain diketopyrrolopyrrole and thiophene with side chains
  作者：You-Ren Liu、Li-Hsin Chan、Horng-Yi Tang

  DOI：10.1002/pola.27767

  日期：2015.12.15

  Two new two‐dimensional conjugated copolymers that contain diketopyrrolopyrrole and thiophene with different π conjugation lengths as side chains, called PDPPMTD and PDPPBTD, were designed and synthesized for use in polymer solar cells (PSCs). The resulting copolymers in the thin film state displayed broad absorption in the visible range with an absorption edge at over 1000 nm, and both had relatively

  设计并合成了两种新型的二维共轭共聚物，称为PDPPMTD和PDPPBTD，它们含有不同的π共轭长度作为侧链的二酮吡咯并吡咯和噻吩，用于聚合物太阳能电池（PSC）。所得的薄膜状态的共聚物在可见光范围内显示出广泛的吸收，吸收边缘超过1000 nm，并且两者均具有相对较低的HOMO水平，分别对于PDPPMTD和PDPPBTD分别为-5.20和-5.18 eV 。基于PDPPBTD / PC61BM（w / w = 1：2）的PSC的功率转换效率（PCE）达到4.10％，J sc为14.5 mA / cm2，V oc为0.59 V，FF为48 ％， 尽管PDPPMTD / PC61BM（w / w = 1：2）的PCE为2.96％，J sc为12.6 mA / cm2，V oc为0.60 V，FF为39％。这些结果表明，化学结构的微调可以显着影响J sc和FF。©2015 Wiley Periodicals，Inc
• Bulky side-chain density effect on the photophysical, electrochemical and photovoltaic properties of polythiophene derivatives
  作者：Hsing-Ju Wang、Li-Hsin Chan、Chih-Ping Chen、Shin-Lei Lin、Rong-Ho Lee、Ru-Jong Jeng

  DOI：10.1016/j.polymer.2010.11.036

  日期：2011.1

  Low band-gap polythiophene (PT) derivatives, with bulky conjugated side-chains composed of the triphenylamine, thiophene, and vinylene groups (TPATh), are synthesized. The copolymers, synthesized by Grignard metathesis and Stille coupling with different copolymer configurations and side-chain densities, are regioregular-TPATh-PT (rr-TPATh-PT) and random-TPATh-PT (r-TPATh-PT), respectively. The incorporation of bulky conjugated moiety curtails the effective conjugation length in the main chain; thus, low HOMO levels are obtained for the copolymers. Moreover, r-TPATh-PT with less bulky side-chain content exhibits a better conjugation along the polymer backbone than rr-TPATh-PT. Higher absorption intensity in the vision region is observed for r-TPATh-PT in comparison with rr-TPATh-PT. In addition, polymer solar cells (PSCs) are fabricated based on an interpenetrating network of PT derivatives as the electron donor and the fullerene derivatives (PC61BM and PC71BM) as the electron acceptors. Better compatibility is observed for the r-TPATh-PT/PC61BM-blend film as compared to the rr-TPATh-PT/PC61BM-blend film. Higher photovoltaic (PV) performances of the r-TPATh-PT/PC61BM-based PSCs are observed in comparison with the rr-TPATh-PT/PC61BM-based PSCs. The power conversion efficiency (PCE) of the PSC based on the blend of r-TPATh-PT and PC61BM (w/w = 1:1) reaches 0.94% under an illumination of AM 1.5G, 100 mW cm(-2), which is almost twice that of the cell based on rr-TPATh-PT. Further improvement of PV performance is achieved for the PSC fabricated from the blend of r-TPATh-PT and fullerene derivative PC71BM (w/w = 1:3), with a short-circuit current of 6.83 mA cm(-2), an open-circuit voltage of 0.71 V and a PCE of 1.75%. (C) 2010 Elsevier Ltd. All rights reserved.