4,7-di-(thiazol-5-yl)-2,1,3-benzothiadiazole | 1422391-04-5

• 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: 4,7-di-(thiazol-5-yl)-2,1,3-benzothiadiazole
• 英文别名: 4,7-Bis(1,3-thiazol-5-yl)-2,1,3-benzothiadiazole；4,7-bis(1,3-thiazol-5-yl)-2,1,3-benzothiadiazole
• CAS: 1422391-04-5
• 化学式: C₁₂H₆N₄S₃
• 分子量: 302.404
• InChiKey: DITIXFKWCGASBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 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：
  136
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-溴苯甲醚 、 4,7-di-(thiazol-5-yl)-2,1,3-benzothiadiazole 在 (acetato-κO)({2-[bis(2-methylphenyl)phosphanyl]phenyl}methyl)palladium 、 三(2-甲氧基苯基)膦 、 caesium carbonate 、 三甲基乙酸 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以67%的产率得到4,7-bis(2-(4-methoxyphenyl)thiazol-5-yl)benzo[c][1,2,5]thiadiazole
  参考文献：
  名称：

  Synthesis by Direct Arylation of Thiazole–Derivatives: Regioisomer Configurations–Optical Properties Relationship Investigation

  摘要：

  The synthesis of thiazole(Tz)-based regioisomer materials using selective direct arylation to avoid any protection steps has been developed. A series of trimers in which the Tz groups sandwich either an electron-rich or an electron-deficient unit, with a regioselective orientation of the respective Tz unit, has therefore been synthesized. This chemical strategy has also been followed to synthesize a second series of pentamers in which the Tz group is used as a pi-conjugated bridge between an electron-rich central unit and electron-deficient end-capping groups and vice versa. On both trimers and pentamers, the effect of Tz orientation on the conjugation properties of the synthesized materials was investigated by a combination of experimental measurements and density functional theory calculations. This study highlights that control of the orientation of the Tz unit leads to the synthesis of the most conjugated regioisomer derivative. The present work gives chemical synthesis tools for the synthesis of selectively oriented Tz-based materials as well as a general guideline for the design of Tz-based materials with the highest conjugation length, including the Tz-orientation effect.

  DOI：

  10.1021/jo501685t
• 作为产物：
  描述：

  噻唑 、 4,7-二溴-2,1,3-苯并噻二唑 在 potassium acetate 、 palladium diacetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 18.0h， 以64%的产率得到4,7-di-(thiazol-5-yl)-2,1,3-benzothiadiazole
  参考文献：
  名称：

  PROCESS FOR THE PREPARATION OF BENZOHETERO [1,3] - DIAZOLE COMPOUNDS DISUBSTITUTED WITH HETEOARYL GROUPS

  摘要：

  制备二取代杂芳并[1,3]二唑化合物的过程包括反应至少一种二取代杂芳并[1,3]二唑化合物和至少一种杂芳基化合物。具有杂芳基的二取代杂芳并[1,3]二唑化合物可优势地用于构建发光太阳能浓缩器（LSC）。此外，具有杂芳基的二取代杂芳并[1,3]二唑化合物可优势地用于构建光伏器件，例如光伏电池、光伏模块、太阳能电池、太阳能模块，均可采用刚性和柔性支撑。具有杂芳基的二取代杂芳并[1,3]二唑化合物还可优势地用作半导体聚合物制备中单体单位的前体。

  公开号：

  US20140221663A1

文献信息

• [EN] PROCESS FOR THE PREPARATION OF BENZOHETERO [ 1, 3 ] - DIAZOLE COMPOUNDS DISUBSTITUTED WITH HETEOARYL GROUPS<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE COMPOSÉS BENZOHÉTÉRO[1,3]-DIAZOLE DISUBSTITUÉ PAR DES GROUPES HÉTÉROARYLE
  申请人：ENI SPA

  公开号：WO2013021315A1

  公开（公告）日：2013-02-14

  Process for the preparation of a benzohetero [ 1, 3 ] diazole compound disubstituted with heteroaryl groups which comprises reacting at least one benzohetero [ 1, 3 ] diazole compound disubstituted with at least one heteroaryl compound. Said benzohetero [ 1, 3 ] diazole compound disubstituted with heteroaryl groups can be advantageously used in the construction of luminescent solar concentrators (LSC). Furthermore, said benzohetero [ 1, 3 ] diazole compound disubstituted with heteroaryl groups can be advantageously used in the construction of photovoltaic devices such as, for example, photovoltaic cells, photovoltaic modules, solar cells, solar modules, on both a rigid and flexible support. Said benzohetero [ 1, 3 ] diazole compound disubstituted with heteroaryl groups can also be advantageously used as a precursor of monomeric units in the preparation of semiconductor polymers.

  制备一种双取代杂芳基苯并杂二唑化合物的过程，包括将至少一种双取代杂芳基苯并杂二唑化合物与至少一种杂芳基化合物反应。该含有杂芳基苯并杂二唑化合物可以优势地用于构建发光太阳能浓缩器（LSC）。此外，该含有杂芳基苯并杂二唑化合物可以优势地用于构建刚性和柔性支撑下的光伏器件，例如光伏电池、光伏模块、太阳能电池和太阳能模块。该含有杂芳基苯并杂二唑化合物也可以优势地用作半导体聚合物制备中单体单元的前体。
• PROCESS FOR THE PREPARATION OF BENZOHETERO [ 1, 3]- DIAZOLE COMPOUNDS DISUBSTITUTED WITH HETEOARYL GROUPS
  申请人：ENI S.p.A.

  公开号：EP2742041A1

  公开（公告）日：2014-06-18
• US9353125B2
  申请人：——

  公开号：US9353125B2

  公开（公告）日：2016-05-31
• US9624212B2
  申请人：——

  公开号：US9624212B2

  公开（公告）日：2017-04-18