1-nitropyrene-8-carboxylic acid | 30269-00-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1-nitropyrene-8-carboxylic acid
• 英文别名: 8-nitropyrene-1-carboxylic acid；8-Nitro-pyren-1-carbonsaeure；8-Nitro-1-pyrenecarboxylic acid
• CAS: 30269-00-2
• 化学式: C₁₇H₉NO₄
• 分子量: 291.263
• InChiKey: APGBNSGRXPPXSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.44
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-nitropyrene-8-carboxylic acid 在 镍 氢气 作用下， 生成 8-Amino-pyren-1-carbonsaeure
  参考文献：
  名称：

  Gerasimenko,Yu.; Poteleshchenko,V.P., Journal of Organic Chemistry USSR (English Translation), 1972, vol. 8, p. 362 - 365

  摘要：

  DOI：
• 作为产物：
  描述：

  1-芘甲酸 在 4-二甲氨基吡啶 、 氯化亚砜 、 dinitrogen tetraoxide 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 1-nitropyrene-8-carboxylic acid
  参考文献：
  名称：

  硝基芘光探针：制造它们，它们有什么用？

  摘要：

  芘衍生物是最广泛使用的有机荧光光探针之一。它们中的许多是用于空穴注入的光敏剂。然而，芘主要是紫外线吸收剂，限制了它们在光子应用中的实用性。芘的硝化将其吸收转移到可见光区。相反，已经衍生化用于共价标记的芘的硝化会产生难以分离的异构体混合物。我们提出了一种获得异构纯硝基芘的稳健程序。NMR 分析提供了区域异构体和二取代硝基芘结构的明确归属。添加的取代基对硝基芘的电子性质的影响可以忽略不计。光激发的硝基芘进行有效的三线态形成，使它们成为三线态敏化剂和光氧化剂的有吸引力的选择。因此，二取代硝基芘的简便可靠的制备为探索其电子和光子效用提供了场所。

  DOI：

  10.1002/ejoc.201501339

文献信息

• Helix Triangle:  Unique Peptide-Based Molecular Architecture
  作者：Kentaro Yoshida、Shin-ichi Kawamura、Tomoyuki Morita、Shunsaku Kimura

  DOI：10.1021/ja061989d

  日期：2006.6.1

  We here report a unique cyclic peptide structure, "helix triangle", as a unique example of peptide-based molecular architecture. The cyclic peptide is designed to have a triangular shape in which three 9mer helical peptide units make the sides and three pyrene derivatives make the apexes. The helical peptide units are ideally linear, and the pyrene units are ideal 60 angular components. The yield of the cyclic peptide was relatively high despite its large cycle size. Absorption and fluorescence spectroscopy revealed that the three pyrene units do not interact with each other electronically, and circular dichroism spectroscopy indicated that the helical peptide units take 3(10)-helical conformation. Geometry optimization by the semi-empirical molecular orbital method gave a triangular structure with 3(10)-helices as the plausible molecular structure. To gain more information on the geometry and demonstrate one example of its self-assemblies, the monolayer of the cyclic peptide was prepared at the air/water interface, and its surface pressure-molecular area isotherm was studied. The isotherm indicated formation of a stable monolayer and suggested that the cyclic peptide actually takes the triangular structure predicted by the geometry optimization. The monolayer was then transferred onto a substrate and characterized by various methods. Ellipsometry and infrared reflection-absorption spectroscopy confirmed that the cyclic peptide has horizontal orientation to the surface in the monolayer. Furthermore, absorption and fluorescence spectroscopy showed that the isolated electronic properties of the pyrene units are intact even in a condensed state in the monolayer.