4-(2-pyren-1-yl-ethyl)-benzonitrile | 400822-57-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 4-(2-pyren-1-yl-ethyl)-benzonitrile
• 英文别名: 4-(2-Pyren-1-ylethyl)benzonitrile
• CAS: 400822-57-3
• 化学式: C₂₅H₁₇N
• 分子量: 331.417
• InChiKey: LDWBOERPKIXMHW-UHFFFAOYSA-N

物化性质

• 沸点：
  536.9±29.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,1-二氯甲醚 、 4-(2-pyren-1-yl-ethyl)-benzonitrile 在 四氯化钛 、 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 二氯甲烷 、 四氢呋喃 、 异丙醇 为溶剂， 生成 1-chloromethyl-8-[2-(4-cyanophenyl)-ethyl]-pyrene 、 1-chloromethyl-6-[2-(4-cyanophenyl)-ethyl]-pyrene
  参考文献：
  名称：

  Phenylene Alkylene Dendrons with Site-Specific Incorporated Fluorescent Pyrene Probes

  摘要：

  [GRAPHICS]This report deals with the synthesis and the spectroscopic properties of two second generation (G2) dendrons with site-specific incorporated phenyl pyrene derivatives as solvatochromic fluorescent probes. The generations that do not carry the probe are equipped with volume dummies, pyrene moieties that do not show a solvatochromic effect. Two complementary G2 phenylene alkylene dendrons were synthesized using Suzuki-Miyaura cross coupling. Most of the reactions used in the 10-step sequence generating the target compounds proceeded in good yields. The incorporated probes can be selectively photoexcited and show solvatochromic shifts that are of the same magnitude as for the free probes in a homogeneous solvent environment. In addition to the chargetransfer fluorescence, a broad emission band is observed that is assigned to an intramolecular exciplex formation between the aryl pyrene chromophores.

  DOI：

  10.1021/jo050302p
• 作为产物：
  描述：

  4-[2-(pyren-1-yl)vinyl]benzonitrile 在 10percent Pd/C magnesium 作用下， 以 丙醇 为溶剂， 反应 24.0h， 以96%的产率得到4-(2-pyren-1-yl-ethyl)-benzonitrile
  参考文献：
  名称：

  作为荧光极性探针模型化合物的芳烃取代芘衍生物的合成和光谱性质

  摘要：

  在本文中，报道了通过 Suzuki 交叉偶联合成各种取代的苯基芘 5a-n 和两个去耦类似物 10 和 17。已经通过荧光光谱研究了这些化合物。已经确定了它们发射带（斯托克斯位移）的溶剂化变色和甲基环己烷和乙腈中的量子产率。此外，还展示了芘-三(2,2'-联吡啶)钌(II)配合物19的晶体结构。

  DOI：

  10.1002/1099-0690(200110)2001:20<3819::aid-ejoc3819>3.0.co;2-w

文献信息

• Phenylene Alkylene Dendrons with Site-Specific Incorporated Fluorescent Pyrene Probes
  作者：Matthias Beinhoff、Wilfried Weigel、Wolfgang Rettig、Irene Bruedgam、Hans Hartl、A. Dieter Schlueter

  DOI：10.1021/jo050302p

  日期：2005.8.1

  [GRAPHICS]This report deals with the synthesis and the spectroscopic properties of two second generation (G2) dendrons with site-specific incorporated phenyl pyrene derivatives as solvatochromic fluorescent probes. The generations that do not carry the probe are equipped with volume dummies, pyrene moieties that do not show a solvatochromic effect. Two complementary G2 phenylene alkylene dendrons were synthesized using Suzuki-Miyaura cross coupling. Most of the reactions used in the 10-step sequence generating the target compounds proceeded in good yields. The incorporated probes can be selectively photoexcited and show solvatochromic shifts that are of the same magnitude as for the free probes in a homogeneous solvent environment. In addition to the chargetransfer fluorescence, a broad emission band is observed that is assigned to an intramolecular exciplex formation between the aryl pyrene chromophores.
• Synthesis and Spectroscopic Properties of Arene-Substituted Pyrene Derivatives as Model Compounds for Fluorescent Polarity Probes
  作者：Matthias Beinhoff、Wilfried Weigel、Martin Jurczok、Wolfgang Rettig、Claudia Modrakowski、Irene Brüdgam、Hans Hartl、A. Dieter Schlüter

  DOI：10.1002/1099-0690(200110)2001:20<3819::aid-ejoc3819>3.0.co;2-w

  日期：2001.10

  In this paper, the syntheses of a variety of substituted phenyl pyrenes 5a−n by Suzuki cross-coupling and of two decoupled analogues 10 and 17 are reported. These compounds have been investigated by fluorescence spectroscopy. The solvatochromism of their emission bands (Stokes shift) and the quantum yields in methylcyclohexane and acetonitrile have been determined. Furthermore, the crystal structure

  在本文中，报道了通过 Suzuki 交叉偶联合成各种取代的苯基芘 5a-n 和两个去耦类似物 10 和 17。已经通过荧光光谱研究了这些化合物。已经确定了它们发射带（斯托克斯位移）的溶剂化变色和甲基环己烷和乙腈中的量子产率。此外，还展示了芘-三(2,2'-联吡啶)钌(II)配合物19的晶体结构。