4-(4'-diphenylaminophenyl)-N-ethylhexyl-1,8-naphthalimide | 1605305-90-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(4'-diphenylaminophenyl)-N-ethylhexyl-1,8-naphthalimide
• 英文别名: 2-(2-ethylhexyl)-6-[4-(N-phenylanilino)phenyl]benzo[de]isoquinoline-1,3-dione
• CAS: 1605305-90-5
• 化学式: C₃₈H₃₆N₂O₂
• 分子量: 552.716
• InChiKey: XYVCPLWXOCFUHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-乙基己胺 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 4-(4'-diphenylaminophenyl)-N-ethylhexyl-1,8-naphthalimide
  参考文献：
  名称：

  New derivatives of triphenylamine and naphthalimide as ambipolar organic semiconductors: Experimental and theoretical approach

  摘要：

  Four new derivatives of triphenylamine containing different number of naphthalimide moieties were designed and synthesized by Suzuki condensation and their properties were studied by the experimental and theoretical tools. The compounds obtained are capable to form molecular glasses with glass transition temperatures ranging from 45 degrees C to 84 degrees C. They exhibit very high thermal stabilities with 5% weight loss temperatures ranging from 429 degrees C to 483 degrees C. Fluorescence quantum yields of the dilute solutions in nonpolar solvents of the synthesized materials range from 0.63 to 0.78. Due to the pronounced electron donor acceptor character, the compounds show dramatic solvatochromic red shifts of fluorescence (up to 250 nm) in polar solvents. The ionization potentials of the solid samples of the compounds established by electron photoemission spectrometry in air ranged from 5.57 to 6.01 eV. 4-(4 '(Di-(4 ''-methoxyphenyl)amino)pheny1)-N-(2-ethylhexyl)-1,8-naphthalimide (5) was found to show ambipolar charge transport in air with the mobilities of charges exceeding 10(-4) cm(2) V-1 s(-1) at high electric fields. The electron mobility of the compounds containing no methoxy groups were found to exceed the hole mobility by 2-3 orders of magnitude. The special role of methoxy groups in the ambipolar charge transport character of compound 5 is discussed in the frame of hopping Marcus theory, by applying a static theoretical analysis followed by a qualitative discussion of the positional disorder in some of these materials. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.dyepig.2014.02.023