N-(3,6,8-tris(methylsulfanyl)pyren-1-yl)acetamide | 159587-83-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: N-(3,6,8-tris(methylsulfanyl)pyren-1-yl)acetamide
• 英文别名: N-[3,6,8-tris(methylsulfanyl)pyren-1-yl]acetamide
• CAS: 159587-83-4
• 化学式: C₂₁H₁₉NOS₃
• 分子量: 397.586
• InChiKey: XFSHMSRPBGOVRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3,6,8-tris(methylsulfanyl)pyren-1-yl)acetamide 在 碘 作用下， 以 various solvent(s) 为溶剂， 以84%的产率得到C₂₁H₁₉NOS₃*C₂₁H₁₉NOS₃⁽¹⁺⁾*I₃^(1-)
  参考文献：
  名称：

  Synthesis and Characterization of Functionalized Analogs of 1,3,6,8-Tetrakis(methylsulfanyl)pyrene and Their Electron-Conducting Radical-Cation Salts

  摘要：

  Radical-cation salts of sulfur-substituted aromatic compounds, formed upon chemical and electrochemical oxidation of the neutral parent compounds, represent an important class of stable electron-conducting materials with many potential uses in molecular-electronics. Many electronic devices require, however, macromolecular materials bound to an electrode surface. While a large number of sulfur-substituted aromatic compounds capable of forming electron-conducting radical-cations salts have been thus far reported, none of them bears functional groups that could be used to bind these compounds to a polymer backbone or an electrode surface. In this paper, we report the synthesis of functionalized analogs of 1,3,6,8-tetrakis(methylsulfanyl)pyrene, where one of the methylsulfanyl groups has been replaced by an amide group. Substitution of the methylsulfanyl group by the amide group does not inhibit the formation of highly electron-conducting radical-cation salts. N-(3,6,8-Tris(methylsulfanyl)pyren-1-yl)acetamide (3a) forms, upon oxidation with iodine, a radical-cation salt (4a) similar to those formed by the parent 1,3,6,8-tetrakis(methylsulfanyl)pyrene 2. The electron-conductivity of radical-cation salt 4a was found to be 1 S cm(-1) at room temperature. The amide group was also used as a handle to introduce additional functionality on the molecule. Coupling of 3,6,8-tris(methylsulfanyl)pyren-1-ylamine (10) with the gamma-carboxyl group of N-(tert-butoxycarbonyl)-L-glutamic acid alpha-tert-butyl ester was achieved via the formation of a mixed anhydride with isobutylchloroformate. This functionalized 3,6,8-(trismethylsulfanyl)pyrene derivative will be used in polymerization reactions onto electrode surfaces, providing a new surface-bound electroactive polymer with potential applications in molecular devices.

  DOI：

  10.1021/ja00101a009
• 作为产物：
  描述：

  N-(1-pyrenyl)acetamide 在 溴 作用下， 以 硝基苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 N-(3,6,8-tris(methylsulfanyl)pyren-1-yl)acetamide
  参考文献：
  名称：

  Synthesis and Characterization of Functionalized Analogs of 1,3,6,8-Tetrakis(methylsulfanyl)pyrene and Their Electron-Conducting Radical-Cation Salts

  摘要：

  Radical-cation salts of sulfur-substituted aromatic compounds, formed upon chemical and electrochemical oxidation of the neutral parent compounds, represent an important class of stable electron-conducting materials with many potential uses in molecular-electronics. Many electronic devices require, however, macromolecular materials bound to an electrode surface. While a large number of sulfur-substituted aromatic compounds capable of forming electron-conducting radical-cations salts have been thus far reported, none of them bears functional groups that could be used to bind these compounds to a polymer backbone or an electrode surface. In this paper, we report the synthesis of functionalized analogs of 1,3,6,8-tetrakis(methylsulfanyl)pyrene, where one of the methylsulfanyl groups has been replaced by an amide group. Substitution of the methylsulfanyl group by the amide group does not inhibit the formation of highly electron-conducting radical-cation salts. N-(3,6,8-Tris(methylsulfanyl)pyren-1-yl)acetamide (3a) forms, upon oxidation with iodine, a radical-cation salt (4a) similar to those formed by the parent 1,3,6,8-tetrakis(methylsulfanyl)pyrene 2. The electron-conductivity of radical-cation salt 4a was found to be 1 S cm(-1) at room temperature. The amide group was also used as a handle to introduce additional functionality on the molecule. Coupling of 3,6,8-tris(methylsulfanyl)pyren-1-ylamine (10) with the gamma-carboxyl group of N-(tert-butoxycarbonyl)-L-glutamic acid alpha-tert-butyl ester was achieved via the formation of a mixed anhydride with isobutylchloroformate. This functionalized 3,6,8-(trismethylsulfanyl)pyrene derivative will be used in polymerization reactions onto electrode surfaces, providing a new surface-bound electroactive polymer with potential applications in molecular devices.

  DOI：

  10.1021/ja00101a009

文献信息

• Li Tiechao, Giasson Richard, J. Amer. Chem. Soc, 116 (1994) N 22, S 9890-9893
  作者：Li Tiechao, Giasson Richard

  DOI：——

  日期：——