diethyl ((7-bromobenzo[c][1,2,5]-thiadiazol-4-yl)methyl)phosphonate | 862974-64-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: diethyl ((7-bromobenzo[c][1,2,5]-thiadiazol-4-yl)methyl)phosphonate
• 英文别名: 4-bromo-7-(diethylphosphonomethyl)benzo-2,1,3-thiadiazole；4-Bromo-7-(diethoxyphosphorylmethyl)-2,1,3-benzothiadiazole
• CAS: 862974-64-9
• 化学式: C₁₁H₁₄BrN₂O₃PS
• 分子量: 365.188
• InChiKey: AWZNNJLFXFFVJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  89.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl ((7-bromobenzo[c][1,2,5]-thiadiazol-4-yl)methyl)phosphonate 在 copper(l) iodide sodium hydride 、 sodium chloride 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 生成
  参考文献：
  名称：

  Stepwise Unidirectional Synthesis of Oligo Phenylene Vinylenes with a Series of Monomers. Use in Plastic Solar Cells

  摘要：

  Four new monomers for directional stepwise synthesis of oligophenylenevinylenes (OPVs) (4-{2[4-(5,5-dimethyl [1,31 dioxan-2-yl)-2,5-dipropoxyphenyl] vinyl }benzyl)phosphonic acid diethyl ester, (5-{2- [4-(5,5-dimethyl [1,31 dioxan-2-yl)-2,5-dipropylphenyl] vinyl }thiophene-2-yl-methyl)phosphonic acid diethyl ester, (5-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropoxyphenyl]vinyl}thiophene-2-yl-methyl)phosphonic acid diethyl ester, and (7-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropylphenyl]-vinyl}benzo[1,2,5]thiadiazol-4-ylmethyl)phosphonic acid diethyl ester have been prepared. Trimeric OPVs were then synthesized and tested as active materials in photovoltaic cells. Conversion efficiencies in the range of 0.5-1% were obtained in blends with the soluble C-60 derivative PCBM. A terpyridine end-functionalized trimer and a heterotrimer with a mixed composition of monomers were also prepared.

  DOI：

  10.1021/jo0506783
• 作为产物：
  描述：

  2,3-二氨基甲苯 在 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 氢溴酸 、 溴 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 溶剂黄146 、 苯 为溶剂， 反应 89.5h， 生成 diethyl ((7-bromobenzo[c][1,2,5]-thiadiazol-4-yl)methyl)phosphonate
  参考文献：
  名称：

  Stepwise Unidirectional Synthesis of Oligo Phenylene Vinylenes with a Series of Monomers. Use in Plastic Solar Cells

  摘要：

  Four new monomers for directional stepwise synthesis of oligophenylenevinylenes (OPVs) (4-{2[4-(5,5-dimethyl [1,31 dioxan-2-yl)-2,5-dipropoxyphenyl] vinyl }benzyl)phosphonic acid diethyl ester, (5-{2- [4-(5,5-dimethyl [1,31 dioxan-2-yl)-2,5-dipropylphenyl] vinyl }thiophene-2-yl-methyl)phosphonic acid diethyl ester, (5-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropoxyphenyl]vinyl}thiophene-2-yl-methyl)phosphonic acid diethyl ester, and (7-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropylphenyl]-vinyl}benzo[1,2,5]thiadiazol-4-ylmethyl)phosphonic acid diethyl ester have been prepared. Trimeric OPVs were then synthesized and tested as active materials in photovoltaic cells. Conversion efficiencies in the range of 0.5-1% were obtained in blends with the soluble C-60 derivative PCBM. A terpyridine end-functionalized trimer and a heterotrimer with a mixed composition of monomers were also prepared.

  DOI：

  10.1021/jo0506783

文献信息

• New low bandgap molecules based on ethylene-separated benzothiadiazoles: synthesis and bandgap comparison
  作者：Yanmei Liu、Hua Lai、Hongliang Zhong、Erjian Xu、Junping Du、Yuxue Li、Qiang Fang

  DOI：10.1016/j.tetlet.2010.06.093

  日期：2010.8

  New ethylene-separated benzothiadiazoles were synthesized for the first time by using a facile procedure, and they showed lower bandgaps than the reported benzothiadiazole-containing compounds. This new benzothiadiazole-containing unit could be introduced into the backbone of the π-conjugated small molecules or polymers to develop new materials with a low bandgap that may have potential applications

  新的乙烯分离的苯并噻二唑是通过一种简便的方法首次合成的，它们的带隙比报道的含苯并噻二唑的化合物低。可以将这种新的含苯并噻二唑的单元引入π共轭小分子或聚合物的骨架中，以开发具有低带隙的新材料，这些材料可能在光电领域具有潜在的应用。
• CHROMOPHORIC POLYMER DOTS WITH NARROW-BAND EMISSION
  申请人：University of Washington through its Center for Commercialization

  公开号：US20140350183A1

  公开（公告）日：2014-11-27

  Polymers, monomers, chromophoric polymer dots and related methods are provided. Highly fluorescent chromophoric polymer dots with narrow-band emissions are provided. Methods for synthesizing the chromophoric polymers, preparation methods for forming the chromophoric polymer dots, and biological applications using the unique properties of narrow-band emissions are also provided.

  本文提供了聚合物、单体、色团聚合物点及相关方法。提供了具有窄带发射的高荧光色团聚合物点。还提供了合成色团聚合物的方法、形成色团聚合物点的制备方法以及利用窄带发射的独特性质进行生物应用的方法。
• Organic Dyes based on Tetraaryl‐1,4‐dihydropyrrolo‐[3,2‐ <i>b</i> ]pyrroles for Photovoltaic and Photocatalysis Applications with the Suppressed Electron Recombination
  作者：Jinfeng Wang、Zhaofei Chai、Siwei Liu、Manman Fang、Kai Chang、Mengmeng Han、Li Hong、Hongwei Han、Qianqian Li、Zhen Li

  DOI：10.1002/chem.201803688

  日期：2018.12.5

  performance in dye‐sensitized solar cells and facilitated photocatalytic hydrogen generation with a highest turnover number (TON) of 4337. Through the detailed investigation of relationship between molecular structures and photovoltaic/photocatalysis property, the connection and difference in molecular design for these two systems are well explained, with the aim to promote the application of dye‐sensitized

  四芳基-1,4-二氢吡咯并[3,2- b ]吡咯（TAPP）带有两个吡咯环和四个苯基部分的部分同时具有很强的供电子能力和非平面构型。一旦作为新的电子给体引入有机染料中，它将有利于增强光收集能力并抑制光伏和光催化系统中的电子复合。通过可调共轭桥和电子受体的连接，相应的有机染料在染料敏化太阳能电池中表现出改善的光伏性能，并促进了光催化制氢，最高周转数（TON）为4337。通过详细研究分子结构之间的关系以及光伏/光催化性能，
• Stepwise Unidirectional Synthesis of Oligo Phenylene Vinylenes with a Series of Monomers. Use in Plastic Solar Cells
  作者：Mikkel Jørgensen、Frederik C. Krebs

  DOI：10.1021/jo0506783

  日期：2005.7.1

  Four new monomers for directional stepwise synthesis of oligophenylenevinylenes (OPVs) (4-2[4-(5,5-dimethyl [1,31 dioxan-2-yl)-2,5-dipropoxyphenyl] vinyl }benzyl)phosphonic acid diethyl ester, (5-2- [4-(5,5-dimethyl [1,31 dioxan-2-yl)-2,5-dipropylphenyl] vinyl }thiophene-2-yl-methyl)phosphonic acid diethyl ester, (5-2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropoxyphenyl]vinyl}thiophene-2-yl-methyl)phosphonic acid diethyl ester, and (7-2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropylphenyl]-vinyl}benzo[1,2,5]thiadiazol-4-ylmethyl)phosphonic acid diethyl ester have been prepared. Trimeric OPVs were then synthesized and tested as active materials in photovoltaic cells. Conversion efficiencies in the range of 0.5-1% were obtained in blends with the soluble C-60 derivative PCBM. A terpyridine end-functionalized trimer and a heterotrimer with a mixed composition of monomers were also prepared.