N,N'-bis(octyl)-3,9-dihydroxy-3,9-bis(phenyl)-1,2,3,7,8,9,13,14-octahydro-perylene-1,2,7,8-tetracarbonyl bisimide | 876274-71-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: N,N'-bis(octyl)-3,9-dihydroxy-3,9-bis(phenyl)-1,2,3,7,8,9,13,14-octahydro-perylene-1,2,7,8-tetracarbonyl bisimide
• 英文别名: N,N'-bis(octyl)-3,9-dihydroxy-3,9-bis(phenyl)-1,2,3,7,8,9,13,14-octahydroperylene-1,2,7,8-tetracarboxyl diimide；8,20-Dihydroxy-5,17-dioctyl-8,20-diphenyl-5,17-diazaheptacyclo[12.10.1.12,9.03,7.015,19.021,25.013,26]hexacosa-1(25),9,11,13(26),21,23-hexaene-4,6,16,18-tetrone
• CAS: 876274-71-4
• 化学式: C₅₂H₅₈N₂O₆
• 分子量: 807.042
• InChiKey: IIVGFFCWDMJCFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  60
• 可旋转键数：
  16
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-bis(octyl)-3,9-dihydroxy-3,9-bis(phenyl)-1,2,3,7,8,9,13,14-octahydro-perylene-1,2,7,8-tetracarbonyl bisimide 在 对甲苯磺酸 、 sulfur 作用下， 以 二苯醚 、 甲苯 为溶剂， 反应 20.0h， 生成 N,N'-bis(octyl)-3,9-bis(phenyl)-perylene-1,2,7,8-tetracarbonyl bisimide
  参考文献：
  名称：

  Twisted, Z-Shaped Perylene Bisimide

  摘要：

  The first derivative of a new class of perylene bisimide chromophores, N,N'-bis(octyl)-3,9-bis(phenyl)perylene-1,2,7,8-tetracarboxyl bisimide, 1, has been synthesized and its fundamental photophysical and electrochemical properties assessed. The extended, Z-shaped structure was achieved by use of the classic photoenolization of an o-methylbenzophenone analogue, 1,5-dibenzoyl-9,10-dihydroanthracene, and in situ Diels-Alder trapping of the resulting o-xylylenol intermediates with N-octylmaleimide. Subsequent dehydration and aromatization of the resulting bisadduct afforded 1. In dichloromethane, bisimide 1 has an absorption lambdamax at 491 nm (epsilon = 29,600 M-1 cm-1), a fluorescence lambdamax at 517 nm with a high quantum yield (Phi = 0.70), and a single-exponential fluorescence decay (tau = 5.01 ns). Pure crystals of 1 have red emission, suggesting exciplex formation in the solid state. X-ray crystallographic analysis of 1 revealed significant twisting of its perylene core.

  DOI：

  10.1021/ja056912o
• 作为产物：
  描述：

  辛胺 以 苯 为溶剂， 反应 19.0h， 生成 N,N'-bis(octyl)-3,9-dihydroxy-3,9-bis(phenyl)-1,2,3,7,8,9,13,14-octahydro-perylene-1,2,7,8-tetracarbonyl bisimide
  参考文献：
  名称：

  Twisted, Z-Shaped Perylene Bisimide

  摘要：

  The first derivative of a new class of perylene bisimide chromophores, N,N'-bis(octyl)-3,9-bis(phenyl)perylene-1,2,7,8-tetracarboxyl bisimide, 1, has been synthesized and its fundamental photophysical and electrochemical properties assessed. The extended, Z-shaped structure was achieved by use of the classic photoenolization of an o-methylbenzophenone analogue, 1,5-dibenzoyl-9,10-dihydroanthracene, and in situ Diels-Alder trapping of the resulting o-xylylenol intermediates with N-octylmaleimide. Subsequent dehydration and aromatization of the resulting bisadduct afforded 1. In dichloromethane, bisimide 1 has an absorption lambdamax at 491 nm (epsilon = 29,600 M-1 cm-1), a fluorescence lambdamax at 517 nm with a high quantum yield (Phi = 0.70), and a single-exponential fluorescence decay (tau = 5.01 ns). Pure crystals of 1 have red emission, suggesting exciplex formation in the solid state. X-ray crystallographic analysis of 1 revealed significant twisting of its perylene core.

  DOI：

  10.1021/ja056912o

文献信息

• FLUORESCENT AROMATIC SENSORS AND THEIR METHODS OF USE
  申请人：Meador Michael A.

  公开号：US20080242870A1

  公开（公告）日：2008-10-02

  Aromatic molecules that can be used as sensors are described. The aromatic sensors include a polycyclic aromatic hydrocarbon core with a five-membered imide rings fused to the core and at least two pendant aryl groups. The aromatic sensor molecules can detect target analytes or molecular strain as a result of changes in their fluorescence, in many cases with on-off behavior. Aromatic molecules that fluoresce at various frequencies can be prepared by altering the structure of the aromatic core or the substituents attached to it. The aromatic molecules can be used as sensors for various applications such as, for example, the detection of dangerous chemicals, biomedical diagnosis, and the detection of damage or strain in composite materials. Methods of preparing aromatic sensor molecules are also described.

  描述了可以用作传感器的芳香分子。这些芳香传感器包括一个多环芳烃核心，该核心上融合了一个五元咪唑环，并且至少有两个侧链芳基基团。这些芳香传感器分子可以通过它们的荧光变化来检测目标分析物或分子应变，许多情况下具有开关行为。可以通过改变芳香核心的结构或连接到其上的取代基来制备在不同频率下发出荧光的芳香分子。这些芳香分子可以用作各种应用的传感器，例如检测危险化学品、生物医学诊断以及复合材料中的损伤或应变的检测。还描述了制备芳香传感器分子的方法。
• US8242162B2
  申请人：——

  公开号：US8242162B2

  公开（公告）日：2012-08-14