5-bromo-2,3-diphenylbenzo[b]thiophene | 23042-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 5-bromo-2,3-diphenylbenzo[b]thiophene
• 英文别名: 5-Bromo-2,3-diphenyl-1-benzothiophene
• CAS: 23042-82-2
• 化学式: C₂₀H₁₃BrS
• 分子量: 365.293
• InChiKey: HEBUZXKPBSRABV-UHFFFAOYSA-N

物化性质

• 熔点：
  176-177 °C
• 沸点：
  475.5±33.0 °C(Predicted)
• 密度：
  1.406±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  22
• 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：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-bromo-2,3-diphenylbenzo[b]thiophene 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 四(三苯基膦)钯 、 potassium acetate 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 72.0h， 生成 9,9'-(5-(triphenylen-2-yl)-1,3-phenylene)bis(9H-carbazole)
  参考文献：
  名称：

  Thermally-stable 2,3-diphenylated benzotiophene containing host materials for red phosphorescent organic light-emitting diodes

  摘要：

  This study reports a series of benzo[b]thiophene (BT) derivatives with good electronic properties as host materials for red phosphorescent organic light-emitting diodes (PHOLEDs). We applied thermally-stable materials for red PHOLEDs which contain BT and carbazole moieties which also provide a good charge transport ability, as well as a good charge confinement effect (T-1 > 2.25 eV). To control the appropriate charge transporting ability, two different structures having one or two carbazole units connected to the single BT moiety were prepared. Using this approach, we found that the material with a single carbazole and a single BT unit showed the best current efficiency and external quantum efficiency (up to 23.6 cd/A and 12.8%, respectively). The results of the experiment also suggest that BT could be used as an electron-transporting unit when utilized with carbazole moiety, although it has previously been utilized as a p-type material. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2014.06.002
• 作为产物：
  描述：

  2,3-diphenylbenzo[b]thiophene 在 溴 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以70%的产率得到5-bromo-2,3-diphenylbenzo[b]thiophene
  参考文献：
  名称：

  Thermally-stable 2,3-diphenylated benzotiophene containing host materials for red phosphorescent organic light-emitting diodes

  摘要：

  This study reports a series of benzo[b]thiophene (BT) derivatives with good electronic properties as host materials for red phosphorescent organic light-emitting diodes (PHOLEDs). We applied thermally-stable materials for red PHOLEDs which contain BT and carbazole moieties which also provide a good charge transport ability, as well as a good charge confinement effect (T-1 > 2.25 eV). To control the appropriate charge transporting ability, two different structures having one or two carbazole units connected to the single BT moiety were prepared. Using this approach, we found that the material with a single carbazole and a single BT unit showed the best current efficiency and external quantum efficiency (up to 23.6 cd/A and 12.8%, respectively). The results of the experiment also suggest that BT could be used as an electron-transporting unit when utilized with carbazole moiety, although it has previously been utilized as a p-type material. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2014.06.002

文献信息

• Radical Cyclization of Arenesulfonyl Chlorides and Alkynes: A Rapid Access to π-Conjugated Benzothio­phenes
  作者：Danyang Wan、Yudong Yang、Xingyan Liu、Mingliang Li、Siling Zhao、Jingsong You

  DOI：10.1002/ejoc.201501439

  日期：2016.1

  A metal-free radical cyclization of arenesulfonyl chlorides with alkynes has been developed, which provides a rapid and practical access to a variety of π-conjugated benzothiophenes with a broad reactive functional group tolerance. Furthermore, dialkynyl compounds could also undergo this transformation to give extended π-systems in good yields.

  已经开发了芳烃磺酰氯与炔烃的金属自由基环化，这为获得各种具有广泛反应官能团耐受性的 π 共轭苯并噻吩提供了快速实用的途径。此外，二炔基化合物也可以进行这种转化，以良好的产率得到扩展的 π 系统。
• Effenberger, Franz; Russ, Werner, Chemische Berichte, 1982, vol. 115, # 12, p. 3719 - 3736
  作者：Effenberger, Franz、Russ, Werner

  DOI：——

  日期：——
• EFFENBERGER, F.;RUSS, W., CHEM. BER., 1982, 115, N 12, 3719-3736
  作者：EFFENBERGER, F.、RUSS, W.

  DOI：——

  日期：——