9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole-3,6-dicarbaldehyde | 1227413-56-0

• 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: 9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole-3,6-dicarbaldehyde
• 英文别名: 9-[2-(2-Methoxyethoxy)ethyl]carbazole-3,6-dicarbaldehyde；9-[2-(2-methoxyethoxy)ethyl]carbazole-3,6-dicarbaldehyde
• CAS: 1227413-56-0
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: JMYGFLUQADLVKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole-3,6-dicarbaldehyde 、 4-溴苄基亚磷酸二乙酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以83%的产率得到
  参考文献：
  名称：

  Fluorescence-Enhanced Chemosensor for Metal Cation Detection Based on Pyridine and Carbazole

  摘要：

  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.

  DOI：

  10.1021/jo401808c
• 作为产物：
  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

文献信息

• Two-photon fluorescence probes for imaging of mitochondria and lysosomes
  作者：Wanggui Yang、Pui Shan Chan、Miu Shan Chan、King Fai Li、Pik Kwan Lo、Nai Ki Mak、Kok Wai Cheah、Man Shing Wong

  DOI：10.1039/c3cc41240g

  日期：——

  Novel biocompatible cyanines show not only a very large two-photon cross-section of up to 5130 GM at 910 nm in aqueous medium for high-contrast and -brightness two-photon fluorescence live cell imaging but also highly selective subcellular localization properties including localization of mitochondria and lysosomes.

  新型生物相容性花青素不仅在水性介质中在910 nm处具有高达5130 GM的非常大的双光子横截面，可用于高对比度和高亮度双光子荧光活细胞成像，而且还具有高度选择性的亚细胞定位特性，包括线粒体和溶酶体。
• Cyanines as New Fluorescent Probes for DNA Detection and Two-Photon Excited Bioimaging
  作者：Xin Jiang Feng、Po Lam Wu、Frédéric Bolze、Heidi W. C. Leung、King Fai Li、Nai Ki Mak、Daniel W. J. Kwong、Jean-François Nicoud、Kok Wai Cheah、Man Shing Wong

  DOI：10.1021/ol100474b

  日期：2010.5.21

  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.
• 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.