12,26,40-Tritert-butyl-44,46,48-trithia-2,4,5,7,16,18,19,21,30,32,33,35,43,45,47-pentadecazadecacyclo[34.6.1.13,6.18,15.117,20.122,29.131,34.09,14.023,28.037,42]octatetraconta-1,3,6,8(47),9(14),10,12,15,17,20,22(45),23(28),24,26,29,31,34,36(43),37(42),38,40-henicosaene | 1058217-51-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 12,26,40-Tritert-butyl-44,46,48-trithia-2,4,5,7,16,18,19,21,30,32,33,35,43,45,47-pentadecazadecacyclo[34.6.1.13,6.18,15.117,20.122,29.131,34.09,14.023,28.037,42]octatetraconta-1,3,6,8(47),9(14),10,12,15,17,20,22(45),23(28),24,26,29,31,34,36(43),37(42),38,40-henicosaene
• 英文别名: 12,26,40-tritert-butyl-44,46,48-trithia-2,4,5,7,16,18,19,21,30,32,33,35,43,45,47-pentadecazadecacyclo[34.6.1.13,6.18,15.117,20.122,29.131,34.09,14.023,28.037,42]octatetraconta-1,3,6,8(47),9(14),10,12,15,17,20,22(45),23(28),24,26,29,31,34,36(43),37(42),38,40-henicosaene
• CAS: 1058217-51-8
• 化学式: C₄₂H₃₉N₁₅S₃
• 分子量: 850.07
• InChiKey: LZGHXTHJKMQKJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  60
• 可旋转键数：
  3
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  260
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  12,26,40-Tritert-butyl-44,46,48-trithia-2,4,5,7,16,18,19,21,30,32,33,35,43,45,47-pentadecazadecacyclo[34.6.1.13,6.18,15.117,20.122,29.131,34.09,14.023,28.037,42]octatetraconta-1,3,6,8(47),9(14),10,12,15,17,20,22(45),23(28),24,26,29,31,34,36(43),37(42),38,40-henicosaene 以 异丙醇 、 丙酮 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Scrutinizing the Chemical Nature and Photophysics of an Expanded Hemiporphyrazine: The Special Case of [30]Trithia-2,3,5,10,12,13,15,20,22,23,25,30-dodecaazahexaphyrin

  摘要：

  Thirty pi-electron-expanded hemiporphyrazines 1a-c have been prepared by crossover condensation reaction of 2,5-diamino-1,3,4-thiadiazole and the corresponding phthalonitrile (3) or diiminoisoindoline (4) derivatives. The expanded azaporphyrin hexamers have been unequivocally characterized by means of spectroscopic, crystallographic, and electrochemical techniques. Weak intramolecular hydrogen bonding imposes a planar conformation to macrocycles. However, the overall electronic delocalization is low, and the nature of the resulting [30]heteroannulene is nonaromatic, as confirmed by NMR studies, XR diffraction analysis, and calculation of the NICS(0) value. Studies on a wide range of physicochemical features including ground, excited, reduced, and oxidized states provide evidence for the wide applicability of these 30 pi-electron-expanded hemiporphyrazines in processes involving electron transfer. A key asset of our work is the systematic development of spectroscopic and kinetic markers for the formation and decay of all of the aforementioned species. Thirty pi-electron-expanded hemiporphyrazines evolve as broadly absorbing light harvesters with excited state energies of around 2.3 eV that are susceptible to facile one-electron reduction and one-electron oxidation reactions.

  DOI：

  10.1021/ja104577d
• 作为产物：
  描述：

  2,5-二氨基-1,3,4-噻二唑 、 4-叔丁基邻苯二甲腈 在 sodium butanolate 作用下， 以 正丁醇 为溶剂， 生成 12,26,40-Tritert-butyl-44,46,48-trithia-2,4,5,7,16,18,19,21,30,32,33,35,43,45,47-pentadecazadecacyclo[34.6.1.13,6.18,15.117,20.122,29.131,34.09,14.023,28.037,42]octatetraconta-1,3,6,8(47),9(14),10,12,15,17,20,22(45),23(28),24,26,29,31,34,36(43),37(42),38,40-henicosaene 、 11,25,40-Tritert-butyl-44,46,48-trithia-2,4,5,7,16,18,19,21,30,32,33,35,43,45,47-pentadecazadecacyclo[34.6.1.13,6.18,15.117,20.122,29.131,34.09,14.023,28.037,42]octatetraconta-1,3,5,7,9(14),10,12,15(47),16,19,21,23(28),24,26,29(45),30,34,36(43),37(42),38,40-henicosaene
  参考文献：
  名称：

  Scrutinizing the Chemical Nature and Photophysics of an Expanded Hemiporphyrazine: The Special Case of [30]Trithia-2,3,5,10,12,13,15,20,22,23,25,30-dodecaazahexaphyrin

  摘要：

  Thirty pi-electron-expanded hemiporphyrazines 1a-c have been prepared by crossover condensation reaction of 2,5-diamino-1,3,4-thiadiazole and the corresponding phthalonitrile (3) or diiminoisoindoline (4) derivatives. The expanded azaporphyrin hexamers have been unequivocally characterized by means of spectroscopic, crystallographic, and electrochemical techniques. Weak intramolecular hydrogen bonding imposes a planar conformation to macrocycles. However, the overall electronic delocalization is low, and the nature of the resulting [30]heteroannulene is nonaromatic, as confirmed by NMR studies, XR diffraction analysis, and calculation of the NICS(0) value. Studies on a wide range of physicochemical features including ground, excited, reduced, and oxidized states provide evidence for the wide applicability of these 30 pi-electron-expanded hemiporphyrazines in processes involving electron transfer. A key asset of our work is the systematic development of spectroscopic and kinetic markers for the formation and decay of all of the aforementioned species. Thirty pi-electron-expanded hemiporphyrazines evolve as broadly absorbing light harvesters with excited state energies of around 2.3 eV that are susceptible to facile one-electron reduction and one-electron oxidation reactions.

  DOI：

  10.1021/ja104577d

文献信息

• Scrutinizing the Chemical Nature and Photophysics of an Expanded Hemiporphyrazine: The Special Case of [30]Trithia-2,3,5,10,12,13,15,20,22,23,25,30-dodecaazahexaphyrin
  作者：Olga N. Trukhina、M. Salomé Rodríguez-Morgade、Silke Wolfrum、Esmeralda Caballero、Natalia Snejko、Elena A. Danilova、Enrique Gutiérrez-Puebla、Mikhail K. Islyaikin、Dirk M. Guldi、Tomás Torres

  DOI：10.1021/ja104577d

  日期：2010.9.22

  Thirty pi-electron-expanded hemiporphyrazines 1a-c have been prepared by crossover condensation reaction of 2,5-diamino-1,3,4-thiadiazole and the corresponding phthalonitrile (3) or diiminoisoindoline (4) derivatives. The expanded azaporphyrin hexamers have been unequivocally characterized by means of spectroscopic, crystallographic, and electrochemical techniques. Weak intramolecular hydrogen bonding imposes a planar conformation to macrocycles. However, the overall electronic delocalization is low, and the nature of the resulting [30]heteroannulene is nonaromatic, as confirmed by NMR studies, XR diffraction analysis, and calculation of the NICS(0) value. Studies on a wide range of physicochemical features including ground, excited, reduced, and oxidized states provide evidence for the wide applicability of these 30 pi-electron-expanded hemiporphyrazines in processes involving electron transfer. A key asset of our work is the systematic development of spectroscopic and kinetic markers for the formation and decay of all of the aforementioned species. Thirty pi-electron-expanded hemiporphyrazines evolve as broadly absorbing light harvesters with excited state energies of around 2.3 eV that are susceptible to facile one-electron reduction and one-electron oxidation reactions.