4-(8-quinolyl)amino-7-nitro-2,1,3-benzoxadiazole | 1424910-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-(8-quinolyl)amino-7-nitro-2,1,3-benzoxadiazole
• 英文别名: 4-(8-Quinolyl)amino-7-nitro-2,1,3-benzoxadiazole；4-nitro-N-quinolin-8-yl-2,1,3-benzoxadiazol-7-amine
• CAS: 1424910-66-6
• 化学式: C₁₅H₉N₅O₃
• 分子量: 307.268
• InChiKey: HQHOIUJZBUXXOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  8-氨基喹啉 、 4-氯-7-硝基苯并-2-氧杂-1,3-二唑 以 三乙胺 为溶剂， 反应 3.0h， 以63.5%的产率得到4-(8-quinolyl)amino-7-nitro-2,1,3-benzoxadiazole
  参考文献：
  名称：

  4-(8-Quinolyl)amino-7-nitro-2,1,3-benzoxadiazole as a new selective and sensitive fluorescent and colorimetric pH probe with dual-responsive ranges in aqueous solutions

  摘要：

  Fluorescent and colorimetric pH probe possess many advantages including rapid response time, nondestructive testing, and excellent pH sensitivity. However, they usually cannot be utilized simultaneously in both acidic and basic pH ranges. In this study, a new selective and sensitive fluorescent and colorimetric pH probe, 4-(8quinolyl)amino-7-nitro-2,1,3-benzoxadiazole (1), was designated and synthesized. The optical probe exhibited dual-responsive pH ranges to both acidic and basic aqueous solutions. When the solution pH was gradually increased from 8.5 to 13.3, the absorption spectra of 1 showed an obvious hyperchromicity, accompanied with a red shift of the absorption band at 340 nm, a blue shift of the absorption band at 482 nm, and a distinct color change from orange to violet pink to yellow. Within the pH range from 2.2 to 0.2, the fluorescent spectra of 1 showed a "turn-on" response signal to solution pH. In order to understand the response mechanism of the probe to solution pH, the probe molecule was split into two parts, 8-aminoquinoline (2) and 4-amino-7- nitrobenzofurazan (3). UV-vis absorption and fluorescent experiments of 2 and 3 indicated that both are sensitive optical pH probes. Furthermore, the NMR experiment of 1 was explored in basic and acidic conditions. The results indicated that the colorimetric responses of 1 to pH under basic condition should be attributed to the deprotonation of the imino group on the quinolyl ring, and the fluorescent recognition of 1 to pH under acidic condition was probably due to the protonation of the nitrogen atoms from the benzofurazan and quinolyl rings. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2015.09.006

文献信息

• 4-(8-Quinolyl)amino-7-nitro-2,1,3-benzoxadiazole as a new colorimetric probe for rapid and visual detection of Hg2+
  作者：Ke Wang、Lixue Yang、Chuan Zhao、Huimin Ma

  DOI：10.1016/j.saa.2012.11.114

  日期：2013.3

  4-Amino-7-nitro-2,1,3-benzoxadiazole (ANBD) usually serves as a scaffold for developing fluorescent probes. In this paper, however, ANBD has been used as a chromogenic unit to design a new colorimetric probe, 4-(8-quinolyl)amino-7-nitro-2,1,3-benzoxadiazole (1), for rapid and visual detection of Hg2+. The reaction of 1 with Hg2+ in NaH2PO4-Na2HPO4 buffer (pH 7.0) containing 70% (v/v) acetonitrile forms a 1:1 complex, accompanying a red shift of the absorption maximum from 482 nm to 557 nm and a distinct color change from orange to violet. Moreover the color reaction exhibits a high selectivity and sensitivity to Hg2+ only, instead of other common metal ions. This behavior may be ascribed to the formation of a specific 1-Hg2+ complex, which is supported by H-1 NMR titration experiments. The present study is not only a supplement to the detection method of Hg2+, but also a merit to the chemistry of 4-amino-7-nitro-2,1,3-benzoxadiazole. (C) 2012 Elsevier B.V. All rights reserved.