12-methyl-12-phenyl-12H-benzo[4,5]thieno[2,3-b]benzo[4,5]thieno[3,2-e][1,4]thiaphosphinin-12-ium trifluoromethanesulfonate | 1245784-76-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫色烯
• 英文名称: 12-methyl-12-phenyl-12H-benzo[4,5]thieno[2,3-b]benzo[4,5]thieno[3,2-e][1,4]thiaphosphinin-12-ium trifluoromethanesulfonate
• CAS: 1245784-76-2
• 化学式: CF₃O₃S*C₂₃H₁₆PS₃
• 分子量: 568.622
• InChiKey: LNBKPXHBLZRTPW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.56
• 重原子数：
  35.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  57.2
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2,3-二溴苯并[b]噻吩 在 正丁基锂 、 四甲基乙二胺 、 双氧水 作用下， 以 四氢呋喃 、 乙醚 、 氯仿 、 水 为溶剂， 反应 2.0h， 生成 12-methyl-12-phenyl-12H-benzo[4,5]thieno[2,3-b]benzo[4,5]thieno[3,2-e][1,4]thiaphosphinin-12-ium trifluoromethanesulfonate
  参考文献：
  名称：

  Ladder-Type π-Conjugated 4-Hetero-1,4-dihydrophosphinines: A Structure-Property Study

  摘要：

  Abstractπ‐Conjugated six‐membered 1,4‐dihydrophosphinines containing a heteroatom (Si, P, S) at the 4 position were synthesized and systematically studied. X‐ray crystallographic analyses showed that the central six‐membered heterocyclic rings are almost planar. The sum of the angles around the phosphorus atom increases by 23° from the trivalent phosphorus to the phosphonium atom in the thiaphosphinine system, which is consistent with the NMR spectroscopic studies. UV/Vis spectroscopy and theoretical calculations revealed that the communication between the phosphorus center and the benzothiophene moiety is enhanced by the incorporation of a sulfur atom into the molecular scaffold. The increased conjugation endows the thiaphosphinines with interesting emission properties. Theoretical calculations supported the postulation that the orbital coupling between the π system and a σ* orbital could be enhanced in the thiaphosphinine system, especially through a phosphonium center. Cyclic voltammetry studies revealed that the thiaphosphinine oxide, thiaphosphonium, and cis‐diphosphinine oxide exhibit quasi‐reversible reduction processes, which demonstrate that simple changes in the bridge heteroatoms help to efficiently tune the redox properties of the ladder‐type 4‐hetero‐1,4‐dihydrophosphinines.

  DOI：

  10.1002/asia.201000196