3-[(4-硝苯基)偶氮基]-9H-咔唑-9-乙醇 | 177100-04-8

• 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
• 中文名称: 3-[(4-硝苯基)偶氮基]-9H-咔唑-9-乙醇
• 中文别名: 3-[(4-硝基苯)偶氮]-9H-咔唑-9-乙醇
• 英文名称: 3-[(4-nitrophenyl)]azo-9H-carbazole-9-ethanol
• 英文别名: 3-[(4-Nitrophenyl)azo]-9H-carbazole-9-ethanol；2-[3-[(4-nitrophenyl)diazenyl]carbazol-9-yl]ethanol
• CAS: 177100-04-8
• 化学式: C₂₀H₁₆N₄O₃
• 分子量: 360.372
• InChiKey: UAWDYRPQXCAZKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  95.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[(4-硝苯基)偶氮基]-9H-咔唑-9-乙醇 、 丙烯酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到(4-nitrophenyl)-[3-[N-[2-(acryloyloxy)ethyl]carbazolyl]]diazene
  参考文献：
  名称：

  FRET-based acrylic nanoparticles with dual-color photoswitchable properties in DU145 human prostate cancer cell line labeling

  摘要：

  Dual-color photoswitchable fluorescent polymer nanoparticles have emerged as an important type of cell detectors. Here, dual-color acrylic nanoparticles containing spiropyran and azo-carbazole derivatives with remarkable photostability and photoreversibility were employed. These prominent properties were attributed to the covalent bonding between the incorporated chromophores and the polymeric matrix and provided efficient fluorescence resonance energy transfer phenomenon. The obtained nanoparticles were purified after dialysis and delivered into DU145 cancer cells. Trypan blue dye exclusion assays showed that these nanoparticles were biocompatible with no toxicity to the cells. Fluorescence microscopy images demonstrated that the prostate cancer cells containing nanoparticles exhibited excellent cell uptake with green and red fluorescence emissions after primary excitation at 410 nm and subsequent irradiation at 365 nm, respectively, depicting their dual-color characteristics. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2016.06.042
• 作为产物：
  描述：

  咔唑 在 盐酸 、 potassium hydroxide 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-[(4-硝苯基)偶氮基]-9H-咔唑-9-乙醇
  参考文献：
  名称：

  FRET Phenomenon in Photoreversible Dual-Color Fluorescent Polymeric Nanoparticles Based on Azocarbazole/Spiropyran Derivatives

  摘要：

  Incorporation of chromophores into a polymer chain results in prominent photoreversibility and fatigue resistance, photostability over the long term, and restriction of the internal conversion (IC). Here, we report the copolymerization of two photoactive monomers with methyl methacrylate via emulsion polymerization in order to obtain photoswitchable dual-color fluorescent nanoparticles. For this purpose, azocarbazole ethyl acrylate (AzoCzEA) and spiropyran ethyl acrylate (SPEA) were synthesized and the fluorescence polymeric latex nanoparticles were prepared correspondingly. FT-IR and (HNMR)-H-1 spectra were used to confirm the structure of novel fluorescent AzoCzEA. UV vis studies of the obtained nanoparticles displayed the spectral features of both AzoCzEA and SPEA under stimuli-irradiation and inclusion of these chromophores into the polymer particles. DSC analysis revealed an increase in Tg of the prepared copolymer, indicating covalently incorporation of the photoactive monomers into the polymer chains. The optimum ratio of two chromophores to achieve complete quenching and highest energy transfer was determined by UV vis spectroscopy. DLS and SEM results demonstrated particle size distribution of 40-80 nm with spherical morphology. Fluorescence spectra revealed remarkable fluorescence resonance energy transfer (FRET) from AzoCzEA to SPEA after UV irradiation at 365 nm and dual-color characteristic of the prepared nanoparticles. Besides, an enhancement in the photoreversibility, photostability, prevention of IC, dye leakage, and aggregation were studied elaborately. The obtained results were attributed to the involvement of such chromophores into the polymeric matrix via covalent bonding. Labeling and tracking of living cells and rewriteable patterning are potential applications for such dual-color fluorescent nanoparticles.

  DOI：

  10.1021/acs.macromol.5b02401

文献信息

• FRET-based acrylic nanoparticles with dual-color photoswitchable properties in DU145 human prostate cancer cell line labeling
  作者：Jaber Keyvan Rad、Ali Reza Mahdavian、Samideh Khoei、Azam Janati Esfahani

  DOI：10.1016/j.polymer.2016.06.042

  日期：2016.8

  Dual-color photoswitchable fluorescent polymer nanoparticles have emerged as an important type of cell detectors. Here, dual-color acrylic nanoparticles containing spiropyran and azo-carbazole derivatives with remarkable photostability and photoreversibility were employed. These prominent properties were attributed to the covalent bonding between the incorporated chromophores and the polymeric matrix and provided efficient fluorescence resonance energy transfer phenomenon. The obtained nanoparticles were purified after dialysis and delivered into DU145 cancer cells. Trypan blue dye exclusion assays showed that these nanoparticles were biocompatible with no toxicity to the cells. Fluorescence microscopy images demonstrated that the prostate cancer cells containing nanoparticles exhibited excellent cell uptake with green and red fluorescence emissions after primary excitation at 410 nm and subsequent irradiation at 365 nm, respectively, depicting their dual-color characteristics. (C) 2016 Elsevier Ltd. All rights reserved.
• FRET Phenomenon in Photoreversible Dual-Color Fluorescent Polymeric Nanoparticles Based on Azocarbazole/Spiropyran Derivatives
  作者：Jaber Keyvan Rad、Ali Reza Mahdavian、Hamid Salehi-Mobarakeh、Amin Abdollahi

  DOI：10.1021/acs.macromol.5b02401

  日期：2016.1.12

  Incorporation of chromophores into a polymer chain results in prominent photoreversibility and fatigue resistance, photostability over the long term, and restriction of the internal conversion (IC). Here, we report the copolymerization of two photoactive monomers with methyl methacrylate via emulsion polymerization in order to obtain photoswitchable dual-color fluorescent nanoparticles. For this purpose, azocarbazole ethyl acrylate (AzoCzEA) and spiropyran ethyl acrylate (SPEA) were synthesized and the fluorescence polymeric latex nanoparticles were prepared correspondingly. FT-IR and (HNMR)-H-1 spectra were used to confirm the structure of novel fluorescent AzoCzEA. UV vis studies of the obtained nanoparticles displayed the spectral features of both AzoCzEA and SPEA under stimuli-irradiation and inclusion of these chromophores into the polymer particles. DSC analysis revealed an increase in Tg of the prepared copolymer, indicating covalently incorporation of the photoactive monomers into the polymer chains. The optimum ratio of two chromophores to achieve complete quenching and highest energy transfer was determined by UV vis spectroscopy. DLS and SEM results demonstrated particle size distribution of 40-80 nm with spherical morphology. Fluorescence spectra revealed remarkable fluorescence resonance energy transfer (FRET) from AzoCzEA to SPEA after UV irradiation at 365 nm and dual-color characteristic of the prepared nanoparticles. Besides, an enhancement in the photoreversibility, photostability, prevention of IC, dye leakage, and aggregation were studied elaborately. The obtained results were attributed to the involvement of such chromophores into the polymeric matrix via covalent bonding. Labeling and tracking of living cells and rewriteable patterning are potential applications for such dual-color fluorescent nanoparticles.