4,7-dibromo-2-methylbenzo[d]thiazole | 1417896-97-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 4,7-dibromo-2-methylbenzo[d]thiazole
• 英文别名: 4,7-Dibromo-2-methylbenzo[d]thiazole；4,7-dibromo-2-methyl-1,3-benzothiazole
• CAS: 1417896-97-9
• 化学式: C₈H₅Br₂NS
• 分子量: 307.008
• InChiKey: WWQMAQGZZNEKOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,7-dibromo-2-methylbenzo[d]thiazole 在 四(三苯基膦)钯 、 ammonium acetate 、 sodium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 52.0h， 生成 2-cyano-3-(5-(4-(4-(diphenylamino)phenyl)-2-methylbenzo[d]thiazol-7-yl)thiophen-2-yl) acrylic acid
  参考文献：
  名称：

  Influence of the benzo[d]thiazole-derived π-bridges on the optical and photovoltaic performance of D–π–A dyes

  摘要：

  New metal-free organic sensitizers containing a benzo[d]thiazole or phenyl unit as the pi-conjugated system, a triphenylamine as an electron donor, and a cyanoacrylic acid moiety as an electron acceptor were synthesized and used for dye-sensitized solar cells. Photophysical and electrochemical properties of these dyes were investigated, and their performances as sensitizers in solar cells were measured. The introduction of a benzo[d]thiazole unit into the molecular structure resulted in a high incident photon-to-current conversion efficiency (more than 70%) from 340 nm to 600 nm. One solar cell containing a benzo[d]thiazole unit, produced a eta of 5.85% (J(SC) = 10.63 mA cm(-2), V-OC = 0.72 V, and ff = 0.77) under 100 mW cm(-2) simulated AM 1.5 G solar irradiation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.11.004
• 作为产物：
  描述：

  2,5-二溴硝基苯 在 吡啶 、 tetraphosphorus decasulfide 、 六甲基二硅氧烷 、 铁粉 、 溶剂黄146 、 potassium hexacyanoferrate(III) 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 6.03h， 生成 4,7-dibromo-2-methylbenzo[d]thiazole
  参考文献：
  名称：

  结合噻唑部分的基于聚合物的荧光传感器，用于直接和视觉检测Hg 2+和Ag +

  摘要：

  通过4,7-二溴-2-甲基苯并[ d ]噻唑与1,4-二乙炔基-2,5-双（辛氧基）苯的聚合反应，通过Pd催化的Sonogashira偶联反应合成了噻唑类共轭聚合物。共轭聚合物发出明亮的绿色荧光，并且相对于其他阳离子（例如Li +，K +，Ca 2 +，Mg 2 +，Ba 2 +，Zn）对Hg 2+和Ag +表现出“熄灭”荧光猝灭响应。2+，Cd 2 +，Co 2 +，Ni 2 +，Pb 2 +，Cu 2 +，Al 3+和Fe3+。更重要的是，在添加Hg 2+（绿色至无色）和Ag +（绿色至黄色）后，用肉眼可以清楚地观察到该聚合物溶液的颜色变化，表明可以使用这种基于噻唑的共轭聚合物材料。作为比色传感器，可直接视觉检测Hg 2+和Ag +。

  DOI：

  10.1016/j.tet.2015.01.052

文献信息

• Influence of the benzo[d]thiazole-derived π-bridges on the optical and photovoltaic performance of D–π–A dyes
  作者：Zhenhua Ci、Xiaoqiang Yu、Ming Bao、Chaolei Wang、Tingli Ma

  DOI：10.1016/j.dyepig.2012.11.004

  日期：2013.3

  New metal-free organic sensitizers containing a benzo[d]thiazole or phenyl unit as the pi-conjugated system, a triphenylamine as an electron donor, and a cyanoacrylic acid moiety as an electron acceptor were synthesized and used for dye-sensitized solar cells. Photophysical and electrochemical properties of these dyes were investigated, and their performances as sensitizers in solar cells were measured. The introduction of a benzo[d]thiazole unit into the molecular structure resulted in a high incident photon-to-current conversion efficiency (more than 70%) from 340 nm to 600 nm. One solar cell containing a benzo[d]thiazole unit, produced a eta of 5.85% (J(SC) = 10.63 mA cm(-2), V-OC = 0.72 V, and ff = 0.77) under 100 mW cm(-2) simulated AM 1.5 G solar irradiation. (C) 2012 Elsevier Ltd. All rights reserved.
• Polymer-based fluorescence sensor incorporating thiazole moiety for direct and visual detection of Hg2+ and Ag+
  作者：Fei Li、Fandian Meng、Yuxiang Wang、Chengjian Zhu、Yixiang Cheng

  DOI：10.1016/j.tet.2015.01.052

  日期：2015.3

  conjugated polymer emits bright green fluorescence and exhibits ‘turn-off’ fluorescent quenching responses towards both Hg2+ and Ag+ over other cations, such as Li+, K+, Ca2+, Mg2+, Ba2+, Zn2+, Cd2+, Co2+, Ni2+, Pb2+, Cu2+, Al3+ and Fe3+. More importantly, the color change of this polymer solution could be clearly observed by the naked eyes upon the addition of Hg2+ (green to colorless) and Ag+ (green

  通过4,7-二溴-2-甲基苯并[ d ]噻唑与1,4-二乙炔基-2,5-双（辛氧基）苯的聚合反应，通过Pd催化的Sonogashira偶联反应合成了噻唑类共轭聚合物。共轭聚合物发出明亮的绿色荧光，并且相对于其他阳离子（例如Li +，K +，Ca 2 +，Mg 2 +，Ba 2 +，Zn）对Hg 2+和Ag +表现出“熄灭”荧光猝灭响应。2+，Cd 2 +，Co 2 +，Ni 2 +，Pb 2 +，Cu 2 +，Al 3+和Fe3+。更重要的是，在添加Hg 2+（绿色至无色）和Ag +（绿色至黄色）后，用肉眼可以清楚地观察到该聚合物溶液的颜色变化，表明可以使用这种基于噻唑的共轭聚合物材料。作为比色传感器，可直接视觉检测Hg 2+和Ag +。