4,7-diethynylbenzo[c][1,2,5]selenadiazole | 1404224-70-9

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 4,7-diethynylbenzo[c][1,2,5]selenadiazole
• 英文别名: 4,7-Diethynyl-2,1,3-benzoselenadiazole；4,7-diethynyl-2,1,3-benzoselenadiazole
• CAS: 1404224-70-9
• 化学式: C₁₀H₄N₂Se
• 分子量: 231.115
• InChiKey: PDVQSMZZHRNAEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.65
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-碘苯甲醚 、 4,7-diethynylbenzo[c][1,2,5]selenadiazole 在 copper(l) iodide 、 bis(triphenylphosphine)palladium(II) dichloride 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以75%的产率得到4,7-bis(2-(4-methoxyphenyl)ethynyl)benzo[c][1,2,5]selenadiazole
  参考文献：
  名称：

  D-π-A benzo[c][1,2,5]selenadiazole-based derivatives via an ethynyl bridge: Photophysical properties, solvatochromism and applications as fluorescent sensors

  摘要：

  A series of novel D-pi-A benzo[c][1,2,5]selenadiazole (BSe)-based derivatives 7a-i including electrondonating/electron-withdrawing groups were prepared by Pd-catalyzed Sonogashira-Hagihara reaction of 4,7-diethynylbenzoselenadiazole with various diiodo aryl compounds. Photophysical properties of these compounds were investigated by absorption and emission spectra analyses. Compound 7c containing methoxy group exhibited positive solvatochromism and its solvatochromic properties were analyzed by the Lippert-Mataga equation and Kamlet-Taft equation, respectively. The resulting compounds showed tunable band gaps in the range of 2.21-2.70 eV using theoretical calculations, which was in good agreement with the results derived from the absorption of UV-vis spectra. In addition, fluorescent sensors 7c and 7d showed highly sensitive response for Hg2+ and traces of water using BSe as an acceptor or a fluorophore in real-time detection, respectively. These findings indicate that BSe-based molecules can be developed as excellent fluorophores for fluorescent material applications. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2014.06.035
• 作为产物：
  描述：

  2,1,3-苯并噻二唑 在 selenium(IV) oxide 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium tetrahydroborate 、 copper(l) iodide 、 氢溴酸 、 溴 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 15.0h， 生成 4,7-diethynylbenzo[c][1,2,5]selenadiazole
  参考文献：
  名称：

  Highly sensitive conjugated polymer fluorescent sensors based on benzochalcogendiazole for nickel ions in real-time detection

  摘要：

  使用苯硒二唑单元和三唑单元作为协同受体合成了两种共轭聚合物荧光传感器，用于高灵敏度检测镍离子。

  DOI：

  10.1039/c4tc01112k

文献信息

• Synthesis, optical and electrochemical properties of novel D-π-A type conjugated polymers based on benzo[c][1,2,5]selenadiazole unit via alkyne module
  作者：Duanqin Li、Hui Li、Miaochang Liu、Jiuxi Chen、Jinchang Ding、Xiaobo Huang、Huayue Wu

  DOI：10.1016/j.polymer.2013.09.017

  日期：2013.10

  Three novel donor-π-acceptor (D-π-A) type conjugated polymers P-1, P-2, and P-3 based on benzo[c][1,2,5]selenadiazole moiety and phenyl or naphthyl group via alkyne module were firstly prepared by Sonogashira–Hagihara reaction of various diiodo aryl compounds with the key monomer 4,7-diethynylbenzo[c] [1,2,5]selenadiazole (M-1), which was synthesized by a strategy of firstly introducing the trimethylsilylacetylene

  三种新型给体- π -受体（d-π-A）型共轭聚合物P-1 ，P-2 ，和P-3基于苯并[ C ^ ] [1,2,5] selenadiazole部分和苯基或萘基经由首先通过各种二碘代芳基化合物与关键单体4,7-二乙炔基苯并[c] [1,2,5]硒代二唑（M-1）的Sonogashira-Hagihara反应制备炔烃模块，该方法是通过首先引入策略合成的三甲基甲硅烷基乙炔柔性基团，然后引入硒原子。聚合物在503至510 nm处显示出明显的吸收峰，并且在576–595 nm范围内出现窄的橙红色或红色荧光，这是因为苯并[ c]] [1,2,5]硒代二唑单元可有效降低这些聚合物的最低未占据分子轨道（LUMO）能级。通过使用不同的芳基供体基团，可以在1.37–1.76 eV的范围内调节这些聚合物的带隙。这些发现表明，这些基于苯并[ c ] [1,2,5]硒代二唑的共轭聚合物可以开发出优异的荧光材料。
• Water-Soluble Bis-triazolyl Benzochalcogendiazole Cycloadducts as Tunable Metal Ion Sensors
  作者：Jonathan J. Bryant、Benjamin D. Lindner、Uwe H. F. Bunz

  DOI：10.1021/jo3024889

  日期：2013.2.1

  A series of bis-triazolyl benzochalcogendiazoles was synthesized to investigate their metal-binding capabilities. These fluorophores were formed through the cycloaddition of an ethynylated benzochalcogendiazole and a water-soluble azide. Variation of the chalcogen heteroatom was seen to affect the photophysical properties as well as the metal-binding activity. These cycloadducts exhibited a distinct response to Cu2+, Ni2+, and Ag+ in water. The binding affinity for the copper and nickel ions increased moving the chalcogen atom from O to Se. Statistical analysis of the spectral data enabled differentiation of Ag+, Cu2+, and Ni2+ ions.
• D-π-A benzo[c][1,2,5]selenadiazole-based derivatives via an ethynyl bridge: Photophysical properties, solvatochromism and applications as fluorescent sensors
  作者：Hui Li、Yang Guo、Yunxiang Lei、Wenxia Gao、Miaochang Liu、Jiuxi Chen、Yuefei Hu、Xiaobo Huang、Huayue Wu

  DOI：10.1016/j.dyepig.2014.06.035

  日期：2015.1

  A series of novel D-pi-A benzo[c][1,2,5]selenadiazole (BSe)-based derivatives 7a-i including electrondonating/electron-withdrawing groups were prepared by Pd-catalyzed Sonogashira-Hagihara reaction of 4,7-diethynylbenzoselenadiazole with various diiodo aryl compounds. Photophysical properties of these compounds were investigated by absorption and emission spectra analyses. Compound 7c containing methoxy group exhibited positive solvatochromism and its solvatochromic properties were analyzed by the Lippert-Mataga equation and Kamlet-Taft equation, respectively. The resulting compounds showed tunable band gaps in the range of 2.21-2.70 eV using theoretical calculations, which was in good agreement with the results derived from the absorption of UV-vis spectra. In addition, fluorescent sensors 7c and 7d showed highly sensitive response for Hg2+ and traces of water using BSe as an acceptor or a fluorophore in real-time detection, respectively. These findings indicate that BSe-based molecules can be developed as excellent fluorophores for fluorescent material applications. (C) 2014 Elsevier Ltd. All rights reserved.
• Highly sensitive conjugated polymer fluorescent sensors based on benzochalcogendiazole for nickel ions in real-time detection
  作者：Yunxiang Lei、Hui Li、Wenxia Gao、Miaochang Liu、Jiuxi Chen、Jinchang Ding、Xiaobo Huang、Huayue Wu

  DOI：10.1039/c4tc01112k

  日期：——

  Two conjugated polymer fluorescent sensors using a benzochalcogendiazole unit and a triazole unit as cooperative receptors were synthesized for the highly sensitive detection of nickel ions.

  使用苯硒二唑单元和三唑单元作为协同受体合成了两种共轭聚合物荧光传感器，用于高灵敏度检测镍离子。