N，N'-二十八烷基-3,4,9,10-per二芳基酰亚胺 | 25834-02-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: N，N'-二十八烷基-3,4,9,10-per二芳基酰亚胺
• 中文别名: N,N'-二十八烷基-3,4,9,10-per二芳基酰亚胺
• 英文名称: N,N'-dioctadecyl-3,4,9,10-perylenebiscarboximide
• 英文别名: N,N'-Dioctadecyl-3,4,9,10-perylenedicarboximide；7,18-dioctadecyl-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone
• CAS: 25834-02-0
• 化学式: C₆₀H₈₂N₂O₄
• 分子量: 895.322
• InChiKey: SPPVDEHBIATCNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.4
• 重原子数：
  66
• 可旋转键数：
  34
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N，N'-二十八烷基-3,4,9,10-per二芳基酰亚胺 在 磺酰氯 、 碘苯 、 碘 作用下， 以 硝基苯 为溶剂， 反应 14.0h， 以31%的产率得到1,6,7,12-Tetrachloro-N-N'-bis(octadecyl)-perylene-3,4,9,10-tetracarboxylic acid diimide
  参考文献：
  名称：

  新型苝-3,4:9,10-双(二甲酰亚胺)和苝-3,4:9,10-双(苯并咪唑)衍生物的合成、电化学和光吸收性能

  摘要：

  一系列在海湾被二或四取代的苝-3,4:9,10-双（二甲酰亚胺）（PBI）和苝-3,4:9,10-双（苯并咪唑）（PTCBI）衍生物通过给电子或吸电子基团的区域已被合成为可溶性 n 型半导体。光吸收光谱和电化学分析表明，湾区的取代性质在调节这些 PBI 和 PTCBI 衍生物的电子特性中起着至关重要的作用。根据理论研究确定的能级检查这些光学和电化学数据，可以建立结构和电子特性之间的关系。

  DOI：

  10.1002/ejoc.201100513
• 作为产物：
  描述：

  十八烷醛肟 在 咪唑 、 红铝 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 N，N'-二十八烷基-3,4,9,10-per二芳基酰亚胺
  参考文献：
  名称：

  Demming, Stefan; Langhals, Heinz, Chemische Berichte, 1988, vol. 121, p. 225 - 230

  摘要：

  DOI：

文献信息

• Green and highly efficient synthesis of perylene and naphthalene bisimides in nothing but water
  作者：Bettina Baumgartner、Anastasiya Svirkova、Johannes Bintinger、Christian Hametner、Martina Marchetti-Deschmann、Miriam M. Unterlass

  DOI：10.1039/c6cc06567h

  日期：——

  A green one-pot hydrothermal route quantitatively generates high-purity fluorescence bisimide dyes without the need for catalysts or organic solvents.

  绿色的一锅法水热路线可定量生成高纯度的荧光双酰亚胺染料，而无需催化剂或有机溶剂。
• Self-assembly, photophysical and electrochemical properties and activation of the TiO₂ photocatalyst by perylene bisimide
  作者：Adhimoolam Senthilraja、Balu Krishnakumar、Meenakshisundaram Swaminathan、Samuthira Nagarajan

  DOI：10.1039/c3nj01356a

  日期：——

  DPBI exists as highly fluorescent molecular wires and DPBI loaded TiO₂ is more efficient in RO4 photodegradation.

  DPBI是高度荧光的分子导线，DPBI负载的TiO₂在RO4光降解中更有效。
• Langhals, H.; Demmig, St.; Potrawa, Th., Journal fur praktische Chemie (Leipzig 1954), 1991, vol. 333, # 5, p. 733 - 748
  作者：Langhals, H.、Demmig, St.、Potrawa, Th.

  DOI：——

  日期：——
• Liquid Crystalline Perylene Diimides:  Architecture and Charge Carrier Mobilities
  作者：Corien W. Struijk、Alexander B. Sieval、Jarno E. J. Dakhorst、Marinus van Dijk、Peter Kimkes、Rob B. M. Koehorst、Harry Donker、Tjeerd J. Schaafsma、Stephen J. Picken、Anick M. van de Craats、John M. Warman、Han Zuilhof、Ernst J. R. Sudhölter

  DOI：10.1021/ja000991g

  日期：2000.11.1

  The phase behavior of three N-alkyl-substituted perylene diimide derivatives is examined by differential scanning calorimetry and polarized optical microscopy. The occurrence of multiple phase transitions indicates several crystalline and several liquid crystalline phases. X-ray diffraction measurements show that the liquid crystalline phases display high structural ordering in all three dimensions: smectic layers are formed, and within these smectic layers an additional ordering in columns is observed. Molecular modeling confirms this result and substantiates smectic ordering with interdigitating alkyl chains that determine the distance between the smectic layers. The ordering in columns is favored by pi-pi interactions between the cofacially oriented perylene molecules and by the elliptic shape of the molecule. Finally, intermolecular dipole-dipole interactions between the carbonyl groups of the imide moieties cause the perylene molecules to orient on average with a slight rotation between neighboring molecules within a columnar stack. Following the determination of the electronic transition dipole moment, this orientation, which still involves substantial pi-pi interactions, could be confirmed by UV/vis spectroscopy of perylene aggregates. To gauge the potential of these materials as organic semiconductors, the charge carrier mobility of one of the perylene derivatives has been measured by pulse-radiolysis time-resolved microwave conductivity. A value in excess of 0.1 cm(2) V-1 s(-1) is found in the liquid crystalline phase, and a value in excess of 0.2 cm(2) V-1 s(-1) is found for the crystalline phase. These values are comparable with the highest values previously found for other discotic materials.
• DEMMING, STEFAN;LANGHALS, HEINZ, CHEM. BER., 121,(1988) N 2, 225-230
  作者：DEMMING, STEFAN、LANGHALS, HEINZ

  DOI：——

  日期：——