N-(1-heptyl-octyl)-perylene-3,4,9,10-tetracarboxylic acid bisimide | 502637-05-0

• 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-(1-heptyl-octyl)-perylene-3,4,9,10-tetracarboxylic acid bisimide
• 英文别名: N-(1-heptyloctyl)-perylene-3,4,9,10-tetracarboxylic bisimide；N-(1-heptyloctyl)-perylene-3,4:9,10-tetracarboxylic diimide；7-Pentadecan-8-yl-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；7-pentadecan-8-yl-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: 502637-05-0
• 化学式: C₃₉H₄₀N₂O₄
• 分子量: 600.758
• InChiKey: WHWQDZZFKUIBLX-UHFFFAOYSA-N

物化性质

• 沸点：
  797.5±42.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(1-heptyl-octyl)-perylene-3,4,9,10-tetracarboxylic acid bisimide 在 吡啶 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 N-(1-heptyloctyl)-N'-(2-ethyloxycarbonyl-2'-anthraquinonyl)-perylene-3,4:9,10-tetracarboxylic bisimide
  参考文献：
  名称：

  双发色per衍生物：来自非荧光发色团的能量转移。

  摘要：

  在非荧光发色团（例如芴酮和蒽醌）处的激发能量已通过快速转移到高荧光per双酰亚胺中而被捕获。为此，蒽醌，芴酮和蒽衍生物已通过非共轭间隔基与per联双酰亚胺连接，并且已确定了此类组件的荧光量子产率与激发波长的关系。在这种组件中的能量转移受两个生色团的取向的强烈影响。这对于荧光开关的构造是令人感兴趣的。

  DOI：

  10.1002/1521-3765(20021216)8:24<5630::aid-chem5630>3.0.co;2-z
• 作为产物：
  描述：

  3,4,9,10-perylenetetracarboxylic-3,4-anhydride-9,10-imide 、 8-十五烷胺 在 咪唑 作用下， 反应 2.0h， 以77%的产率得到N-(1-heptyl-octyl)-perylene-3,4,9,10-tetracarboxylic acid bisimide
  参考文献：
  名称：

  双发色per衍生物：来自非荧光发色团的能量转移。

  摘要：

  在非荧光发色团（例如芴酮和蒽醌）处的激发能量已通过快速转移到高荧光per双酰亚胺中而被捕获。为此，蒽醌，芴酮和蒽衍生物已通过非共轭间隔基与per联双酰亚胺连接，并且已确定了此类组件的荧光量子产率与激发波长的关系。在这种组件中的能量转移受两个生色团的取向的强烈影响。这对于荧光开关的构造是令人感兴趣的。

  DOI：

  10.1002/1521-3765(20021216)8:24<5630::aid-chem5630>3.0.co;2-z

文献信息

• Synthesis of a π-extended TTF–perylenediimide donor–acceptor dyad
  作者：Rafael Gómez、Carmen Coya、José L. Segura

  DOI：10.1016/j.tetlet.2008.03.091

  日期：2008.5

  A donor-acceptor dyad containing perylenediimide as the electron acceptor and pi-extended tetrathiafulvalene as electron donor has been successfully synthesized by means of a Wittig reaction. Cyclic voltammetry and absorption spectroscopy show that both electroactive units preserve their nature, whereas preliminar photophysical investigations show a strong fluorescence quenching. (c) 2008 Elsevier Ltd. All rights reserved.
• NMRP versus “Click” Chemistry for the Synthesis of Semiconductor Polymers Carrying Pendant Perylene Bisimides
  作者：Andreas S. Lang、Anne Neubig、Michael Sommer、Mukundan Thelakkat

  DOI：10.1021/ma100708h

  日期：2010.9.14

  The synthesis of well-defined polymers with pendant perylene bisimide (PBI) groups by a combination of nitroxide-mediated radical polymerization (NMRP) of trimethylsilyl propargyl acrylate followed by copper-catalyzed azide-alkyne cycloaddition (CuAAC, "click" chemistry) is described. The kinetics of NMRP of trimethylsilyl propargyl acrylate polymerization was monitored by H-1 NMR and size exclusion chromatography (SEC). Almost quantitative conversion in the "click" reaction with an azide functionalized PBI derivative was proven by Fritz and H-1 NMR analysis. Thus, semiconductor polymers carrying PBI pendant groups with M-n up to 15800 g.mol(-1) and polydispersity indices as good as 1.16 were obtained by this route. These polymers were compared with poly(perylene bisimide acrylate)s, PPerAcr-(CH2)(11), and PPerAcr(CH2)(6), which were synthesized by direct NMRP of PBI acrylates. These samples do not carry any triazol unit and they differ in their spacer length connecting the PBI unit to the main chain. All polymers were comparatively studied by SEC, thermogravimetry, differential scanning calorimetry, polarization microscopy, UV/vis spectroscopy, and photoluminescence measurements. The crystalline structure of the polymers was analyzed by X-ray diffraction. Inductively coupled plasma mass spectrometry analysis confirmed that copper content in the "click" polymer could be reduced down to 126 ppm (w/w).
• Bichromophoric Perylene Derivatives: Energy Transfer from Non-Fluorescent Chromophores
  作者：Heinz Langhals、Sigrid Saulich

  DOI：10.1002/1521-3765(20021216)8:24<5630::aid-chem5630>3.0.co;2-z

  日期：2002.12.16

  The energy of excitation at non-fluorescent chromophores such as fluorenone and anthraquinone has been trapped by a fast energy transfer to the highly fluorescent perylene bisimides. To this end, anthraquinone, fluorenone and anthracene derivatives have been linked to the perylene bisimides by non-conjugating spacers and fluorescence quantum yield of such assemblies have been determined as a function

  在非荧光发色团（例如芴酮和蒽醌）处的激发能量已通过快速转移到高荧光per双酰亚胺中而被捕获。为此，蒽醌，芴酮和蒽衍生物已通过非共轭间隔基与per联双酰亚胺连接，并且已确定了此类组件的荧光量子产率与激发波长的关系。在这种组件中的能量转移受两个生色团的取向的强烈影响。这对于荧光开关的构造是令人感兴趣的。
• Swallow-Tail Substituted Liquid Crystalline Perylene Bisimides: Synthesis and Thermotropic Properties
  作者：André Wicklein、Andreas Lang、Mathis Muth、Mukundan Thelakkat

  DOI：10.1021/ja905260c

  日期：2009.10.14

  unsymmetrically substituted. We avoided substitution at bay positions of the perylene core to maintain the planarity and strong pi-pi interactions, which favor intermolecular order and charge carrier transport. The thermotropic behavior, which is strongly influenced by the nature of the substituents was investigated using differential scanning calorimetry (DSC), polarization optical microscopy (POM), and X-ray

  介绍了几种燕尾 N-取代苝双酰亚胺 (PBI) 染料的定制合成和结构-性能关系。PBI 衍生物是通过两种不同的合成方法合成的，本文对细节进行了评估。所有 PBI 都带有烷基燕尾或低聚乙二醇醚 (OEG) 燕尾部分作为 N 取代基，其中许多是不对称取代的。我们避免在苝核的海湾位置进行取代，以保持平面性和强 pi-pi 相互作用，这有利于分子间有序和电荷载流子传输。使用差示扫描量热法 (DSC)、偏振光学显微镜 (POM) 和 X 射线衍射测量 (XRD) 研究了受取代基性质强烈影响的热致行为。在大多数情况下，OEG 燕尾单元的引入促进了热致液晶行为，并且不对称取代允许调整中间相宽度。中间相表现出特征的柱状六边形 (Col(h)) 堆积，这是由共面取向的苝分子之间的 pi-pi 相互作用引起的。因此，通过仅在酰亚胺位置加入柔性 OEG 燕尾单元，可以有效抑制 PBI 分子的固有结晶趋势。这种分