3,4,9-triphenylperylene | 1415803-83-6

• 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: 3,4,9-triphenylperylene
• 英文别名: 3,4,9-Triphenylperylene
• CAS: 1415803-83-6
• 化学式: C₃₈H₂₄
• 分子量: 480.609
• InChiKey: ABIJNHKKSLQWSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  38
• 可旋转键数：
  3
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  苯硼酸酐 、 苝 在 邻四氯苯醌 、 palladium diacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以17%的产率得到3-phenylperylene
  参考文献：
  名称：

  Palladium-catalyzed direct phenylation of perylene: structural and optical properties of 3,4,9-triphenylperylene and 3,4,9,10-tetraphenylperylene

  摘要：

  We have developed one-step synthesis of multiphenylperylenes from perylene through palladium-catalyzed oxidative C-H/C-B coupling using phenylboroxin as a phenyl source. The combination of Pd(OAc)(2) as a catalyst and o-chloranil as an oxidant is the key for direct C-H arylation of perylene. The X-ray crystallography of 3,4,9-triphenylperylene (3) and 3,4,9,10-tetraphenylperylene (4) revealed twisted structures of petylene core caused by steric repulsion of neighboring phenyl groups. Compounds 3 and 4 showed red shift in both absorption and fluorescence spectra compared to perylene whereas absolute fluorescence quantum yields are similarly high (Phi(F)=0.94). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.037

文献信息

• EP2730554
  申请人：——

  公开号：——

  公开（公告）日：——
• Palladium-catalyzed direct phenylation of perylene: structural and optical properties of 3,4,9-triphenylperylene and 3,4,9,10-tetraphenylperylene
  作者：Katsuaki Kawasumi、Kenji Mochida、Yasutomo Segawa、Kenichiro Itami

  DOI：10.1016/j.tet.2013.01.037

  日期：2013.6

  We have developed one-step synthesis of multiphenylperylenes from perylene through palladium-catalyzed oxidative C-H/C-B coupling using phenylboroxin as a phenyl source. The combination of Pd(OAc)(2) as a catalyst and o-chloranil as an oxidant is the key for direct C-H arylation of perylene. The X-ray crystallography of 3,4,9-triphenylperylene (3) and 3,4,9,10-tetraphenylperylene (4) revealed twisted structures of petylene core caused by steric repulsion of neighboring phenyl groups. Compounds 3 and 4 showed red shift in both absorption and fluorescence spectra compared to perylene whereas absolute fluorescence quantum yields are similarly high (Phi(F)=0.94). (C) 2013 Elsevier Ltd. All rights reserved.