5,7-dibromo-2,3-bis(2-ethylhexyl)thieno[3,4-b]pyrazine | 1203451-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 1,3-噻唑并[5,4-d]嘧啶
• 英文名称: 5,7-dibromo-2,3-bis(2-ethylhexyl)thieno[3,4-b]pyrazine
• CAS: 1203451-24-4
• 化学式: C₂₂H₃₄Br₂N₂S
• 分子量: 518.399
• InChiKey: DPZWTBJNYUXFLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.73
• 重原子数：
  27.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  25.78
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5,7-dibromo-2,3-bis(2-ethylhexyl)thieno[3,4-b]pyrazine 在 (1,1′-(1,8-naphthyridine-2,7-diyl) bis(N-(2,6-disopropylphenyl)ethan-1-imine))Ni₂Br₂ 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2,3-bis(2-ethylhexyl)thienopyrazine
  参考文献：
  名称：

  具有氧化还原活性配体的双核配合物促进共轭聚合物合成的链增长机制

  摘要：

  证明了具有氧化还原活性配体的双核镍配合物作为引发剂用于供体和受体共轭单体的链增长聚合的效用。机理分析表明，多个金属中心与氧化还原活性配体的偶联允许获得新的自由基途径，从而扩展了共轭聚合物合成的已知方法。

  DOI：

  10.1002/anie.202206044
• 作为产物：
  描述：

  5,10-diethyltetradecane-7,8-dione 在 N-溴代丁二酰亚胺(NBS) 、 sodium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 5,7-dibromo-2,3-bis(2-ethylhexyl)thieno[3,4-b]pyrazine
  参考文献：
  名称：

  具有氧化还原活性配体的双核配合物促进共轭聚合物合成的链增长机制

  摘要：

  证明了具有氧化还原活性配体的双核镍配合物作为引发剂用于供体和受体共轭单体的链增长聚合的效用。机理分析表明，多个金属中心与氧化还原活性配体的偶联允许获得新的自由基途径，从而扩展了共轭聚合物合成的已知方法。

  DOI：

  10.1002/anie.202206044

文献信息

• Photocontrolled Synthesis of n‐Type Conjugated Polymers
  作者：Eliot F. Woods、Alexandra J. Berl、Julia A. Kalow

  DOI：10.1002/anie.201915819

  日期：2020.4.6

  synthesize π-conjugated polymers (CPs) are dominated by thermally driven, transition-metal-mediated reactions. Herein we show that electron-deficient Grignard monomers readily polymerize under visible-light irradiation at room temperature in the absence of a catalyst. The product distribution can be tuned by the wavelength of irradiation based on the absorption of the polymer. Conversion studies are

  目前合成π-共轭聚合物（CP）的方法主要由热驱动的过渡金属介导的反应控制。在本文中，我们表明缺乏电子的格氏单体在室温下在不存在催化剂的情况下在可见光辐射下容易聚合。可以基于聚合物的吸收通过照射的波长来调节产物分布。转化研究与不受控制的链增长过程一致；相应地，扩链产生全共轭的n型嵌段共聚物。初步结果表明，可以将聚合反应扩展为供体-受体交替共聚物。我们预计，该方法可以用作访问n型CP的新体系结构的平台，而无需过渡金属催化。
• Synthesis and Characterization of Bridged Bithiophene-Based Conjugated Polymers for Photovoltaic Applications: Acceptor Strength and Ternary Blends
  作者：Chiu-Hsiang Chen、Chao-Hsiang Hsieh、Martin Dubosc、Yen-Ju Cheng、Chain-Shu Hsu

  DOI：10.1021/ma902206u

  日期：2010.1.26

  Six of three-component donor-acceptor random copolymers P1-P6, symbolized as (thiophene donor)(m)-(thiophene acceptor)(n), were rationally designed and successfully synthesized by the palladium-catalyzed Stille Coupling, The 4H-cyclopenta[2, 1-b:3,4-b']dithiophene (CPDT) unit serves as the donor for P1-P4, while file benzothiadiazole (BT), quinoxaline (QU), dithienoquinoxaline, and thienopyrazine (TP) units are used as the acceptor for P1, P2, P3, and P4, respectively. P5 and P6 are structurally analogous to P1 and P2 except for using the dithieno[3.2-b:2',3'-d]silole (DTS) unit as the donor. Because the band gap lowering ability of the acceptor units in the polymer is in the order TP > BR > QU presumably due to the quinoid form Population in the polymers, the optical band gaps call be well adjusted to be 1.2, 1.6, and 1.8 eV for P4, P1, and P2, respectively. It is found that file two bridged bithiophene units, CPDT and DTS, have similar steric and electronic effects oil the P1 and P5 as well as P2 and P6, respectively, leading to comparable intrinsic properties and device performances. Bulk heterojunction photovoltaic cells based oil ITO/PEDOT:PSS/polymer:PC71BM/Ca/Al configuration were fabricated and characterized. Although P4 exhibits the lowest optical band gap, broadest absorption spectrum, and highest mobility, the too low-lying LUMO level hinders the efficient exciton dissociation, resulting in a low PCE of 0.7%. Compared with poly[2,6-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b']dithiophene)-alt-4,7-(2,1,3-benzothiadiazole)] (PCPDTBT), random copolymer P1 shows more blue-shifted, broader absorption spectrum, comparable mobility, and a higher PCE of 2.0%. In view of the fact that P1 shows it higher band gap with strong absorption in visible region, while PCPDTBT-has a lower band gap to mainly absorb NIR light, a BHJ device with the active layer containing ternary blend of PCPDTBT/P-1/PC71BM was investigated and achieved an enhanced PCE of 2.5%, which outperforms the devices based on the binary blending systems of PCPDTBT/PC7, BM (PCE = 1.4%) or P1/PC71 BM (PCE = 2.0%,,) Linder the identical conditions. Such an improvement is ascribed to file complementary absorption and compatible structure of P1 and PCPDTBT polymers.