8-Phenyl-4,12-bis(1-phenyltriazol-4-yl)-3,13-dithia-8-phosphatricyclo[8.3.0.02,6]trideca-1(10),2(6),4,11-tetraene-7,9-dione | 1417639-18-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 8-Phenyl-4,12-bis(1-phenyltriazol-4-yl)-3,13-dithia-8-phosphatricyclo[8.3.0.02,6]trideca-1(10),2(6),4,11-tetraene-7,9-dione
• 英文别名: 8-phenyl-4,12-bis(1-phenyltriazol-4-yl)-3,13-dithia-8-phosphatricyclo[8.3.0.02,6]trideca-1(10),2(6),4,11-tetraene-7,9-dione
• CAS: 1417639-18-9
• 化学式: C₃₂H₁₉N₆O₂PS₂
• 分子量: 614.648
• InChiKey: AUFSSGOPJKLMPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  43
• 可旋转键数：
  5
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3,3',5,5'-四溴-2,2'-联噻吩 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 草酰氯 、 Cu(PPh3)3Br 、 二异丙胺 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 、 三苯基膦 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 86.5h， 生成 8-Phenyl-4,12-bis(1-phenyltriazol-4-yl)-3,13-dithia-8-phosphatricyclo[8.3.0.02,6]trideca-1(10),2(6),4,11-tetraene-7,9-dione
  参考文献：
  名称：

  Dithieno[3,2-c:2′,3′-e]-2,7-diketophosphepin: A Unique Building Block for Multifunctional π-Conjugated Materials

  摘要：

  A series of conjugated materials based on the new dithieno[3,2-c:2',3'-e]-2,7-diketophosphepin (DTDKP) building block have been studied for the first time. Theoretical calculations predict DTDKP to be a better electron acceptor than the well-known dithienophosphole and the nitrogen analogue, bithiopheneimide. Cyclic voltammetry studies revealed two reduction processes that support their promising electron-acceptor properties, and modification of the P center with O or gold(I) further reduced the LUMO energy to ca. -3.6 eV. Expansion of the DTDKP core with various aromatic moieties has been realized using the Huisgen alkynyl click reaction, resulting in altered optical and electrochemical properties with compounds showing a high-energy absorption band at ca. 270-290 nm and a low-energy band at ca. 390-460 nm. The acceptor character of the DTDKP core was demonstrated by a red shift following the electron-donating strength of the appended aromatic moiety. Intriguing white-light emission from just a single species with the CIE coordinates of (0.33, 0.34) was observed for some of the extended species as the result of an unexpected dual-emission behavior. The high-energy emission in the blue-to-green region and the low-energy emission in the orange-to-red region are attributed to a pi* -> pi transition of the DTDKP core and charge transfer from the triazole moiety to DTDKP, respectively. Apart from tuning of the molecular properties, this novel building block has also been applied in a self-assembled organogel, which exhibited pronounced luminescence. Scanning electron microscopy confirmed that the gel self-assembled by forming a network of entangled ID fibrous structures on the micrometer scale.

  DOI：

  10.1021/ja310680x