4,4'-(4,4,9,9-tetrakis(4-hexylphenyl)-4,9-dihydro-sec-indaceno[1,2-b:5,6-b']dithiophene-2,7-diyl)bis(7-bromo-[1,2,5]thiadiazolo[3,4-c]pyridine) | 1415665-84-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 4,4'-(4,4,9,9-tetrakis(4-hexylphenyl)-4,9-dihydro-sec-indaceno[1,2-b:5,6-b']dithiophene-2,7-diyl)bis(7-bromo-[1,2,5]thiadiazolo[3,4-c]pyridine)
• 英文别名: 4,4'-(4,4,9,9-tetrakis-(4-hexylphenyl)-4,9-dihydro-s-indaceno[1,2-b:5,6-b']dithiophene-2,7-diyl)bis(7-bromo[1,2,5]thiadiazolo[3,4-c]pyridine)；7-Bromo-4-[15-(7-bromo-[1,2,5]thiadiazolo[3,4-c]pyridin-4-yl)-9,9,18,18-tetrakis(4-hexylphenyl)-5,14-dithiapentacyclo[10.6.0.03,10.04,8.013,17]octadeca-1(12),2,4(8),6,10,13(17),15-heptaen-6-yl]-[1,2,5]thiadiazolo[3,4-c]pyridine；7-bromo-4-[15-(7-bromo-[1,2,5]thiadiazolo[3,4-c]pyridin-4-yl)-9,9,18,18-tetrakis(4-hexylphenyl)-5,14-dithiapentacyclo[10.6.0.03,10.04,8.013,17]octadeca-1(12),2,4(8),6,10,13(17),15-heptaen-6-yl]-[1,2,5]thiadiazolo[3,4-c]pyridine
• CAS: 1415665-84-7
• 化学式: C₇₄H₇₄Br₂N₆S₄
• 分子量: 1335.51
• InChiKey: HMLONIVUHSYULR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  25.1
• 重原子数：
  86
• 可旋转键数：
  26
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  190
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4,7-二溴-[1,2,5]噻二唑并[3,4-c]吡啶 、 2,7-二(三甲基锡)-4,4,9,9-四(对己基苯)-引达省并二噻吩 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 1.17h， 以83%的产率得到4,4'-(4,4,9,9-tetrakis(4-hexylphenyl)-4,9-dihydro-sec-indaceno[1,2-b:5,6-b']dithiophene-2,7-diyl)bis(7-bromo-[1,2,5]thiadiazolo[3,4-c]pyridine)
  参考文献：
  名称：

  Regioregular pyridyl[2,1,3]thiadiazole-co-indacenodithiophene conjugated polymers

  摘要：

  我们合成了含有吡啶并[2,1,3]噻二唑（PT）和茚并噻吩（IDT）交替结构单元的正交共轭聚合物。在这些共聚物中，PT 上的吡啶基氮原子沿着骨架精确排列，因此每个氮原子在两个 IDT 侧翼单元上都有一个相邻的近端和一个相邻的远端对应物。我们发现，尽管在轨道能级和光带隙方面没有明显的差异，但通过使用场效应晶体管器件测定，这些团状材料表现出更大的电荷载流子迁移率，与富勒烯混合制成体异质结活性层时，可产生更高的太阳能电池功率转换效率。

  DOI：

  10.1039/c3cc43229g

文献信息

• Regioregular pyridal[2,1,3]thiadiazole π-conjugated copolymers for organic semiconductors
  申请人：Bazan Guillermo C.

  公开号：US09293708B2

  公开（公告）日：2016-03-22

  A method of regioselectively preparing a pyridine-containing compound is provided. In particular embodiments, the method includes reacting halogen-functionalized pyridal[2,1,3]thiadiazole with organotin-functionalized cyclopenta[2,1-b:3,4-b′]dithiophene or organotin-functionalized indaceno[1,2-b:5,6-b′]dithiophene. Also provided is a method of preparing a polymer. The method includes regioselectively preparing a monomer that includes a pyridal[2,1,3]thiadiazole unit; and reacting the monomer to produce a polymer that includes a regioregular conjugated backbone section, wherein the section includes a repeat unit containing the pyridal[2,1,3]thiadiazole unit. A polymer that includes a regioregular conjugated backbone section, and electronic devices that include the polymer, are also provided.

  提供了一种区域选择性制备含吡啶化合物的方法。在特定实施例中，该方法包括将卤素功能化的吡啶[2,1,3]噻二唑与有机锡功能化的环戊[2,1-b:3,4-b']二硫噻吩或有机锡功能化的吲哚并[1,2-b:5,6-b']二硫噻吩反应。还提供了一种制备聚合物的方法。该方法包括区域选择性制备包含吡啶[2,1,3]噻二唑单元的单体，并将单体反应以产生包含区域富集的共轭骨架部分的聚合物，其中该部分包含重复单元，其中包含吡啶[2,1,3]噻二唑单元。还提供了包含区域富集的共轭骨架部分的聚合物和包含该聚合物的电子器件。
• REGIOREGULAR PYRIDAL[2,1,3]THIADIAZOLE PI-CONJUGATED COPOLYMERS FOR ORGANIC SEMICONDUCTORS
  申请人：BAZAN Guillermo C.

  公开号：US20120322966A1

  公开（公告）日：2012-12-20

  A method of regioselectively preparing a pyridine-containing compound is provided. In particular embodiments, the method includes reacting halogen-functionalized pyridal[2,1,3]thiadiazole with organotin-functionalized cyclopenta[2,1-b:3,4-b′]dithiophene or organotin-functionalized indaceno[1,2-b:5,6-b′]dithiophene. Also provided is a method of preparing a polymer. The method includes regioselectively preparing a monomer that includes a pyridal[2,1,3]thiadiazole unit; and reacting the monomer to produce a polymer that includes a regioregular conjugated backbone section, wherein the section includes a repeat unit containing the pyridal[2,1,3]thiadiazole unit. A polymer that includes a regioregular conjugated backbone section, and electronic devices that include the polymer, are also provided.

  提供了一种区域选择性制备含吡啶化合物的方法。特别地，该方法包括将卤代功能化的吡啶并[2,1,3]噻二唑与有机锡功能化的环戊[2,1-b:3,4-b′]二硫苯或有机锡功能化的吲哚并[1,2-b:5,6-b′]二硫苯反应。还提供了一种制备聚合物的方法。该方法包括区域选择性地制备包含吡啶并[2,1,3]噻二唑单元的单体；并反应该单体以产生包含区域规则的共轭骨架部分的聚合物，其中该部分包含含有吡啶并[2,1,3]噻二唑单元的重复单元。还提供了一种包含区域规则的共轭骨架部分的聚合物和包含该聚合物的电子器件。
• US9293708B2
  申请人：——

  公开号：US9293708B2

  公开（公告）日：2016-03-22
• Regioregular pyridyl[2,1,3]thiadiazole-co-indacenodithiophene conjugated polymers
  作者：Wen Wen、Lei Ying、Ben B. Y. Hsu、Yuan Zhang、Thuc-Quyen Nguyen、Guillermo C. Bazan

  DOI：10.1039/c3cc43229g

  日期：——

  Regioregular conjugated polymers containing alternating pyridyl[2,1,3]thiadiazole (PT) and indacenodithiophene (IDT) structural units were synthesized. In these copolymers, the pyridyl nitrogen atoms on PT are precisely arranged along the backbone so that each one has an adjacent proximal and an adjacent distal counterpart across the two IDT flanking units. We find that despite the absence of obvious differences in orbital energy levels and optical bandgap, the regioregular materials exhibit larger charge carrier mobilities, as determined by using field effect transistor devices, and can yield higher solar cell power conversion efficiencies when mixed with fullerenes in bulk heterojunction active layers.

  我们合成了含有吡啶并[2,1,3]噻二唑（PT）和茚并噻吩（IDT）交替结构单元的正交共轭聚合物。在这些共聚物中，PT 上的吡啶基氮原子沿着骨架精确排列，因此每个氮原子在两个 IDT 侧翼单元上都有一个相邻的近端和一个相邻的远端对应物。我们发现，尽管在轨道能级和光带隙方面没有明显的差异，但通过使用场效应晶体管器件测定，这些团状材料表现出更大的电荷载流子迁移率，与富勒烯混合制成体异质结活性层时，可产生更高的太阳能电池功率转换效率。