N,N'-di(2-trifluoroethyl)-1,7-dibromoperylene-3,4,9,10-tetracarboxylic acid bisimide | 1079752-94-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N,N'-di(2-trifluoroethyl)-1,7-dibromoperylene-3,4,9,10-tetracarboxylic acid bisimide
• 英文别名: N,N'-bis(2,2,2-trifluoroethyl)-1,7-dibromo-perylene-3,4:9,10-bis(dicarboximide)
• CAS: 1079752-94-5
• 化学式: C₂₈H₁₀Br₂F₆N₂O₄
• 分子量: 712.197
• InChiKey: AASSFQDSHKFZEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.58
• 重原子数：
  42.0
• 可旋转键数：
  2.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  74.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N,N'-di(2-trifluoroethyl)-1,7-dibromoperylene-3,4,9,10-tetracarboxylic acid bisimide 、 氰化锌 在 tris-(dibenzylideneacetone)dipalladium(0) 作用下， 以71%的产率得到N,N'-bis(2,2,2-trifluoroethyl)-1,7-dicyano-perylene-3,4:9,10-bis(dicarboximide)
  参考文献：
  名称：

  Organic n-Channel Transistors Based on Core-Cyanated Perylene Carboxylic Diimide Derivatives

  摘要：

  Five core-cyanated perylene carboxylic diimides end-functionalized with fluorine-containing linear and cyclic substituents have been synthesized and employed in the fabrication of air-stable n-channel organic thin-film field-effect transistors with carrier mobilities up to 0.1 cm(2)/Vs. The relationships between molecular structure, thin-film morphology, substrate temperature during vacuum deposition, transistor performance, and air stability have been investigated. Our experiments led us to conclude that the role of the fluorine functionalization in the air-stable n-channel operation of the transistors is different than previously thought.

  DOI：

  10.1021/ja074675e
• 作为产物：
  描述：

  2,2,2-三氟乙基胺 、 1,7-二溴-3,4,9,10-苝四羧基双酐 以62%的产率得到N,N'-di(2-trifluoroethyl)-1,7-dibromoperylene-3,4,9,10-tetracarboxylic acid bisimide
  参考文献：
  名称：

  Organic n-Channel Transistors Based on Core-Cyanated Perylene Carboxylic Diimide Derivatives

  摘要：

  Five core-cyanated perylene carboxylic diimides end-functionalized with fluorine-containing linear and cyclic substituents have been synthesized and employed in the fabrication of air-stable n-channel organic thin-film field-effect transistors with carrier mobilities up to 0.1 cm(2)/Vs. The relationships between molecular structure, thin-film morphology, substrate temperature during vacuum deposition, transistor performance, and air stability have been investigated. Our experiments led us to conclude that the role of the fluorine functionalization in the air-stable n-channel operation of the transistors is different than previously thought.

  DOI：

  10.1021/ja074675e

文献信息

• Perylenebisimide regioisomers: Effect of substituent position on their spectroscopic, electrochemical, and photovoltaic properties
  作者：Ying Liu、Yang Wang、Ling Ai、Zhiyang Liu、Xinhua Ouyang、Ziyi Ge

  DOI：10.1016/j.dyepig.2015.05.032

  日期：2015.10

  New disubstituent fluorinated perylenebisimide regioisomers were synthesized and characterized. The single-crystal structure of a 1,6-disubstituted perylenebisimide was elucidated for the first time, which revealed that the molecules are arranged in stacks along the b-axis of the unit cell and share more than 50% of their core surface. Owing to the steric encumbrance of the substituents, the perylene cores were highly twisted. The effect of substituent positions on their spectroscopic, electrochemical, and photovoltaic properties were also examined. Moreover, the two substituent positions on perylenebisimides were found to have a large impact on the solar cell performance. Different perylenebisimide regioisomers made an impact on open circuit voltage, but strongly affected the short circuit current density, indirectly influencing the overall photovoltaic performance of the device. (C) 2015 Elsevier Ltd. All rights reserved.