3,6-diethynylcarbazole-9-carboxylic acid 1,1-dimethyltridecyl ester | 935682-38-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3,6-diethynylcarbazole-9-carboxylic acid 1,1-dimethyltridecyl ester
• 英文别名: 2-Methyltetradecan-2-yl 3,6-diethynylcarbazole-9-carboxylate；2-methyltetradecan-2-yl 3,6-diethynylcarbazole-9-carboxylate
• CAS: 935682-38-5
• 化学式: C₃₂H₃₉NO₂
• 分子量: 469.667
• InChiKey: JDGGKKWFSZVDPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,6-diethynylcarbazole-9-carboxylic acid 1,1-dimethyltridecyl ester 、 4-苯甲酰-4`-溴联苯 在 copper(l) iodide 、 tris(dibenzylideneacetone)dipalladium (0) 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以69%的产率得到3,6-bis(benzoylbiphenyl)ethynylcarbazole-9-carboxylic acid 1,1-dimethyltridecyl ester
  参考文献：
  名称：

  Detection of Explosives with a Fluorescent Nanofibril Film

  摘要：

  A new type of fluorescence sensory material has been developed from an alkoxycarbonyl-substituted carbazole-cornered tetracycle. Films fabricated from such materials are shown to be efficient in detecting explosive vapor, probably owing to the extended 1D molecular stacking between the component molecules and intrinsic nanoporous morphology thus formed within the film. The former facilitates long-range exciton migration, while the latter favors adsorption and diffusion of gaseous adsorbates within the film. A combination of these two characteristics enables efficient fluorescence quenching of the film by gaseous quenchers.

  DOI：

  10.1021/ja070747q
• 作为产物：
  描述：

  3,6-二溴咔唑 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 哌啶 、 4-二甲氨基吡啶 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.75h， 生成 3,6-diethynylcarbazole-9-carboxylic acid 1,1-dimethyltridecyl ester
  参考文献：
  名称：

  Detection of Explosives with a Fluorescent Nanofibril Film

  摘要：

  A new type of fluorescence sensory material has been developed from an alkoxycarbonyl-substituted carbazole-cornered tetracycle. Films fabricated from such materials are shown to be efficient in detecting explosive vapor, probably owing to the extended 1D molecular stacking between the component molecules and intrinsic nanoporous morphology thus formed within the film. The former facilitates long-range exciton migration, while the latter favors adsorption and diffusion of gaseous adsorbates within the film. A combination of these two characteristics enables efficient fluorescence quenching of the film by gaseous quenchers.

  DOI：

  10.1021/ja070747q

文献信息

• Flourescent organic nanofibrils as sensory materials for explosives detection
  申请人：Zang Ling

  公开号：US20090233374A1

  公开（公告）日：2009-09-17

  The present invention relates to a class of fluorescent, organic nanofibrils, and particularly the films comprising entangled piling of these nanofibrils exhibiting effective quenching of their fluorescence upon exposure the vapor of explosives. The invention also relates to a sensor and a method for sensing the explosives vapor and other volatile organic compounds, including the explosives taggants through the modulation of the fluorescence of the nanofibril film and the electrical conductivity of the nanofibrils. The invention also relates to a development of synthetic methods, protocols and techniques that leads to production of various arylene-ethynylene macrocycle (AEM) molecules, which consist of a shape-persistent, toroidal scaffold in planar conformation, with minimal ring strain and highly tunable ring sizes (from 0.5 nm to above 10 nm). The invention also relates to an approach to optimization of the one-dimensional molecular arrangement along the long axis of the nanofibril, which provides increased exciton (excited state) migration (via cofacial intermolecular electronic coupling) and charge transport (via pi-electronic delocalization). A combination of long-range exciton migration and efficient charge transport makes the nanofibrils ideal as sensory materials for detecting explosives and other volatile organic compounds through both optical and electrical sensing mechanisms.
• FLUORESCENT ORGANIC NANOFIBRILS AS SENSORY MATERIALS FOR EXPLOSIVES DETECTION
  申请人：Zang Ling

  公开号：US20120288950A1

  公开（公告）日：2012-11-15

  A class of fluorescent, organic nanofibrils, and particularly the films comprising entangled piling of these nanofibrils exhibiting effective quenching of their fluorescence upon exposure the vapor of explosives is disclosed. A sensor and a method for sensing the explosives vapor and other volatile organic compounds is disclosed, including the explosives taggants through the modulation of the fluorescence of the nanofibril film and the electrical conductivity of the nanofibrils. A development of synthetic methods is disclosed, such as protocols and techniques that lead to the production of various arylene-ethynylene macrocycle (AEM) molecules, which consist of a shape-persistent, toroidal scaffold in planar conformation, with minimal ring strain and highly tunable ring sizes (from 0.5 nm to above 10 nm). An approach to optimization of the one-dimensional molecular arrangement along the long axis of the nanofibril is also disclosed, which provides increased exciton migration and charge transport (via pi-electronic delocalization).
• US8153065B2
  申请人：——

  公开号：US8153065B2

  公开（公告）日：2012-04-10
• Detection of Explosives with a Fluorescent Nanofibril Film
  作者：Tammene Naddo、Yanke Che、Wei Zhang、Kaushik Balakrishnan、Xiaomei Yang、Max Yen、Jincai Zhao、Jeffrey S. Moore、Ling Zang

  DOI：10.1021/ja070747q

  日期：2007.6.6

  A new type of fluorescence sensory material has been developed from an alkoxycarbonyl-substituted carbazole-cornered tetracycle. Films fabricated from such materials are shown to be efficient in detecting explosive vapor, probably owing to the extended 1D molecular stacking between the component molecules and intrinsic nanoporous morphology thus formed within the film. The former facilitates long-range exciton migration, while the latter favors adsorption and diffusion of gaseous adsorbates within the film. A combination of these two characteristics enables efficient fluorescence quenching of the film by gaseous quenchers.