2-[5,8,11,14,17-penta(3,7-dimethyloctanyl)hexa-peri-hexabenzocoronene]butyl-1-pyrene carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 2-[5,8,11,14,17-penta(3,7-dimethyloctanyl)hexa-peri-hexabenzocoronene]butyl-1-pyrene carboxylate
• 英文别名: 4-[11,20,25,34,39-Pentakis(3,7-dimethyloctyl)-6-tridecacyclo[28.12.0.02,15.03,8.04,41.09,14.013,18.016,29.017,22.023,28.027,32.031,36.037,42]dotetraconta-1(42),2,4(41),5,7,9(14),10,12,15,17,19,21,23,25,27,29,31(36),32,34,37,39-henicosaenyl]butyl pyrene-1-carboxylate；4-[11,20,25,34,39-pentakis(3,7-dimethyloctyl)-6-tridecacyclo[28.12.0.02,15.03,8.04,41.09,14.013,18.016,29.017,22.023,28.027,32.031,36.037,42]dotetraconta-1(42),2,4(41),5,7,9(14),10,12,15,17,19,21,23,25,27,29,31(36),32,34,37,39-henicosaenyl]butyl pyrene-1-carboxylate
• 化学式: C₁₁₃H₁₃₄O₂
• 分子量: 1524.31
• InChiKey: WXBFUSQVJMMAAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  41.5
• 重原子数：
  115
• 可旋转键数：
  42
• 环数：
  17.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-芘甲酸 、 2-(4-hydroxybutyl)-5,8,11,14,17-penta(3,7-dimethyloctanyl)hexa-peri-hexabenzocoronene 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以70%的产率得到2-[5,8,11,14,17-penta(3,7-dimethyloctanyl)hexa-peri-hexabenzocoronene]butyl-1-pyrene carboxylate
  参考文献：
  名称：

  Ordered Architectures of a Soluble Hexa-peri-hexabenzocoronene−Pyrene Dyad:  Thermotropic Bulk Properties and Nanoscale Phase Segregation at Surfaces

  摘要：

  An alkylated hexa-peri-hexabenzocoronene with a covalently tethered pyrene unit serves as a model to study self-assembling discotic pi-system dyads both in the bulk and at a surface. Wide-angle X-ray scattering, polarized light microscopy, and differential scanning calorimetry revealed bulk self-assembly into columnar structures. Relative to a control without a tethered pyrene, the new dyad exhibits a more ordered columnar phase at room temperature but with dramatically lowered isotropization temperature, facilitating homeotropic alignment. These two features are important for processing such materials into molecular electronic devices, e.g., photovoltaic diodes. Scanning tunneling microscopy at a solution-solid interface revealed uniform nanoscale segregation of the large from the small pi-systems, leading to a well-defined two-dimensional crystalline monolayer, the likes of which may be employed in the future to study intramolecular electron transfer processes at surfaces, on the molecular scale.

  DOI：

  10.1021/ja028609i

文献信息

• Ordered Architectures of a Soluble Hexa-<i>p</i><i>eri</i>-hexabenzocoronene−Pyrene Dyad:  Thermotropic Bulk Properties and Nanoscale Phase Segregation at Surfaces
  作者：Natalia Tchebotareva、Xiaomin Yin、Mark D. Watson、Paolo Samorì、Jürgen P. Rabe、Klaus Müllen

  DOI：10.1021/ja028609i

  日期：2003.8.1

  An alkylated hexa-peri-hexabenzocoronene with a covalently tethered pyrene unit serves as a model to study self-assembling discotic pi-system dyads both in the bulk and at a surface. Wide-angle X-ray scattering, polarized light microscopy, and differential scanning calorimetry revealed bulk self-assembly into columnar structures. Relative to a control without a tethered pyrene, the new dyad exhibits a more ordered columnar phase at room temperature but with dramatically lowered isotropization temperature, facilitating homeotropic alignment. These two features are important for processing such materials into molecular electronic devices, e.g., photovoltaic diodes. Scanning tunneling microscopy at a solution-solid interface revealed uniform nanoscale segregation of the large from the small pi-systems, leading to a well-defined two-dimensional crystalline monolayer, the likes of which may be employed in the future to study intramolecular electron transfer processes at surfaces, on the molecular scale.