3,6-dibromo-9-[2-(2-methoxyethoxy)ethyl]carbazole | 1073369-83-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,6-dibromo-9-[2-(2-methoxyethoxy)ethyl]carbazole
• 英文别名: 3,6-Dibromo-9-[2-(2-methoxyethoxy)ethyl]carbazole
• CAS: 1073369-83-1
• 化学式: C₁₇H₁₇Br₂NO₂
• 分子量: 427.135
• InChiKey: ARTBGQUZGVCXAD-UHFFFAOYSA-N

物化性质

• 沸点：
  512.0±50.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  23.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-甲酰吗啉 、 3,6-dibromo-9-[2-(2-methoxyethoxy)ethyl]carbazole 在 正丁基锂 作用下， 以48%的产率得到9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole-3,6-dicarbaldehyde
  参考文献：
  名称：

  Cyanines as New Fluorescent Probes for DNA Detection and Two-Photon Excited Bioimaging

  摘要：

  A series of cyanine fluorophores based on fused aromatics as an electron donor for DNA sensing and two-photon bioimaging were synthesized, among which the carbazole-based biscyanine exhibits high sensitivity and efficiency as a fluorescent light-up probe for dsDNA, which shows selective binding toward the AT-rich regions. The synergetic effect of the bischromophoric skeleton gives a several-fold enhancement in a two-photon absorption cross-section as well as a 25- to 100-fold enhancement in two-photon excited fluorescence upon dsDNA binding.

  DOI：

  10.1021/ol100474b
• 作为产物：
  描述：

  9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以91%的产率得到3,6-dibromo-9-[2-(2-methoxyethoxy)ethyl]carbazole
  参考文献：
  名称：

  Cyanines as New Fluorescent Probes for DNA Detection and Two-Photon Excited Bioimaging

  摘要：

  A series of cyanine fluorophores based on fused aromatics as an electron donor for DNA sensing and two-photon bioimaging were synthesized, among which the carbazole-based biscyanine exhibits high sensitivity and efficiency as a fluorescent light-up probe for dsDNA, which shows selective binding toward the AT-rich regions. The synergetic effect of the bischromophoric skeleton gives a several-fold enhancement in a two-photon absorption cross-section as well as a 25- to 100-fold enhancement in two-photon excited fluorescence upon dsDNA binding.

  DOI：

  10.1021/ol100474b

文献信息

• Quantitative real time sensing reveals enhanced sensitivity of polar dendrimer thin films for plastic explosive taggants
  作者：Andrew J. Clulow、Hamish Cavaye、Guoqiang Tang、Paul E. Shaw、Justin J. Cooper-White、Paul L. Burn、Paul Meredith

  DOI：10.1039/c5tc01967b

  日期：——

  A method of introducing pulses of analyte vapours has been developed to study the interactions of nitro-containing analytes with fluorescent sensing films.

  已开发一种引入分析物蒸气脉冲的方法，用于研究含硝基分析物与荧光传感薄膜的相互作用。
• Fluorescence-Enhanced Chemosensor for Metal Cation Detection Based on Pyridine and Carbazole
  作者：Xin Jiang Feng、Pin Zhan Tian、Zheng Xu、Shao Fu Chen、Man Shing Wong

  DOI：10.1021/jo401808c

  日期：2013.11.15

  A series of donor-acceptor systems incorporating a carbazole moiety as the donating unit and pyridine moiety as the accepting unit have been designed and synthesized. The spectroscopic and electrochemical behaviors of the carbazole derivatives demonstrate that the carbazole unit interacts with the electron-accepting group through the pi-conjugated spacer, thus leading to the intramolecular charge transfer (ICT). The pyridine-substituted carbazole derivatives show significant sensing and coordinating properties toward a wide range of metal cations. Compound S2 exhibits fluorescence enhancement upon association with transition metal cations, and compound V3 shows high selectivity for Cu2+ among this series of materials. DFT calculations indicate the different association abilities of the dyes and the enhancement of ICT upon addition of the metal cations.