10-methyl-10-phenyl-10H-benzo[b]phosphindolo[2,3-d]thiophen-10-ium trifluoromethanesulfonate | 1263143-08-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 10-methyl-10-phenyl-10H-benzo[b]phosphindolo[2,3-d]thiophen-10-ium trifluoromethanesulfonate
• CAS: 1263143-08-3
• 化学式: CF₃O₃S*C₂₁H₁₆PS
• 分子量: 480.468
• InChiKey: HGIIDOUPDXACNZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  31.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  57.2
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-bromo-2-(2-bromophenyl)benzo[b]thiophene 在 正丁基锂 、 四甲基乙二胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 10-methyl-10-phenyl-10H-benzo[b]phosphindolo[2,3-d]thiophen-10-ium trifluoromethanesulfonate
  参考文献：
  名称：

  Dually Switchable Heterotetracenes: Addressing the Photophysical Properties and Self-Organization of the P−S System

  摘要：

  New ladder-type, phosphorus- and sulfur-based heterotetracenes were synthesized, which allowed the engineering of the materials' properties by exploitation of the different reactivities between sulfur and phosphorus. P-31 NMR. spectroscopy and X-ray crystallographic studies revealed that the different electronic effects of the secondary heteroatom, sulfur, influence not only the conjugation in the heterotetracene core but also the behavior of the phosphorus center. UV-vis and fluorescence spectroscopy showed that the scaffold's band gap is mainly controlled by the electronic nature of sulfur, while the fluorescence quantum yield highly depends on the electronic nature of phosphorus. Cyclic voltammetry indicated that the redox properties of the system could be altered by selective modification of the respective heteroatom (oxidation of sulfur and/or functionalization of trivalent phosphorus). Importantly, oxidation of the phosphorus center results in enhanced reduction features of the heterotetracene system, and oxidation of the sulfur center further enhances the electron acceptor character of the core. Theoretical calculations provided insights on both selectivity of phosphorus chemistry and communication between the two heteroatoms (sulfur and phosphorus). Macroscopic self-organization of the heterotetracenes was observed when the tetracene core is functionalized with pendant functional groups. Preliminary results showed that extension of the molecule with an alkyl chain along the long axis of molecules induces the formation of ID microfibers, which was confirmed by fluorescence microscopy and scanning electron microscopy.

  DOI：

  10.1021/ja108081b