4,4',4''-tris(triisopropylsilylethynyl)dehydrotribenzo[12]annulene | 1169835-90-8

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 4,4',4''-tris(triisopropylsilylethynyl)dehydrotribenzo[12]annulene
• 英文别名: 2-[14,22-Bis[2-tri(propan-2-yl)silylethynyl]-6-tetracyclo[18.4.0.04,9.012,17]tetracosa-1(20),4(9),5,7,12(17),13,15,21,23-nonaen-2,10,18-triynyl]ethynyl-tri(propan-2-yl)silane
• CAS: 1169835-90-8
• 化学式: C₅₇H₇₂Si₃
• 分子量: 841.455
• InChiKey: DDHMUPIBKQUGME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.91
• 重原子数：
  60
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  4,4',4''-tris(triisopropylsilylethynyl)dehydrotribenzo[12]annulene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以94%的产率得到4,4',4'-triethynyldehydrotribenzo[12]annulene
  参考文献：
  名称：

  Synthesis and Properties of Oligo[n]cruciforms: Nanosized Sterically Encumbered Tetraethynylphenyl-Homologated Fluorophores

  摘要：

  A series of nanosized phenylencethynylenes have been prepared which are sterically insulated from the surrounding environment by multiple functionalization with triisopropylsilyl (TIPS) substituents. The phenyleneethynylenes comprise oligo[n]cruciforms 1-4 (n = 3-5) and a dehydrotribenzo[12]annulene 5, the former of which possess para-acyclic and the latter ortho-cyclic electronic conjugation pathways. All compounds were characterized by H-1 and C-13 NMR, IR, and mass spectroscopic techniques. The X-ray crystal structure of 1 confirmed the sterically isolating properties of the TIPS substituents. A comparison of the physical properties of these electronically differing systems revealed that they were all luminescent upon UV irradiation displayed negligible aggregation in dilute solution and that particular members of the series studied were electrochemically active, undergoing facile reversible reductions. The phenyleneethynylenes also exhibited significantly enhanced thermal stability by virtue of the presence of the TIPS substituents. The properties of 1-5 suggest that they are promising building blocks for the construction of materials for novel molecular electronics applications.

  DOI：

  10.1021/jo802797e
• 作为产物：
  描述：

  2-iodo-4-triisopropylsilylethynyl-ethynylbenzene 在 吡啶 、 potassium tert-butylate 、 copper(l) chloride 作用下， 反应 14.0h， 以20%的产率得到4,4',4''-tris(triisopropylsilylethynyl)dehydrotribenzo[12]annulene
  参考文献：
  名称：

  Synthesis and Properties of Oligo[n]cruciforms: Nanosized Sterically Encumbered Tetraethynylphenyl-Homologated Fluorophores

  摘要：

  A series of nanosized phenylencethynylenes have been prepared which are sterically insulated from the surrounding environment by multiple functionalization with triisopropylsilyl (TIPS) substituents. The phenyleneethynylenes comprise oligo[n]cruciforms 1-4 (n = 3-5) and a dehydrotribenzo[12]annulene 5, the former of which possess para-acyclic and the latter ortho-cyclic electronic conjugation pathways. All compounds were characterized by H-1 and C-13 NMR, IR, and mass spectroscopic techniques. The X-ray crystal structure of 1 confirmed the sterically isolating properties of the TIPS substituents. A comparison of the physical properties of these electronically differing systems revealed that they were all luminescent upon UV irradiation displayed negligible aggregation in dilute solution and that particular members of the series studied were electrochemically active, undergoing facile reversible reductions. The phenyleneethynylenes also exhibited significantly enhanced thermal stability by virtue of the presence of the TIPS substituents. The properties of 1-5 suggest that they are promising building blocks for the construction of materials for novel molecular electronics applications.

  DOI：

  10.1021/jo802797e

文献信息

• Synthesis and Properties of Oligo[<i>n</i>]cruciforms: Nanosized Sterically Encumbered Tetraethynylphenyl-Homologated Fluorophores
  作者：Abdelaziz Al Ouahabi、Paul N. W. Baxter、Jean-Paul Gisselbrecht、André De Cian、Lydia Brelot、Nathalie Kyritsakas-Gruber

  DOI：10.1021/jo802797e

  日期：2009.7.3

  A series of nanosized phenylencethynylenes have been prepared which are sterically insulated from the surrounding environment by multiple functionalization with triisopropylsilyl (TIPS) substituents. The phenyleneethynylenes comprise oligo[n]cruciforms 1-4 (n = 3-5) and a dehydrotribenzo[12]annulene 5, the former of which possess para-acyclic and the latter ortho-cyclic electronic conjugation pathways. All compounds were characterized by H-1 and C-13 NMR, IR, and mass spectroscopic techniques. The X-ray crystal structure of 1 confirmed the sterically isolating properties of the TIPS substituents. A comparison of the physical properties of these electronically differing systems revealed that they were all luminescent upon UV irradiation displayed negligible aggregation in dilute solution and that particular members of the series studied were electrochemically active, undergoing facile reversible reductions. The phenyleneethynylenes also exhibited significantly enhanced thermal stability by virtue of the presence of the TIPS substituents. The properties of 1-5 suggest that they are promising building blocks for the construction of materials for novel molecular electronics applications.