2-(4-hydroxybutyl)-5,8,11,14,17-penta(3,7-dimethyloctanyl)hexa-peri-hexabenzocoronene | 596093-95-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 2-(4-hydroxybutyl)-5,8,11,14,17-penta(3,7-dimethyloctanyl)hexa-peri-hexabenzocoronene
• 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]butan-1-ol；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]butan-1-ol
• CAS: 596093-95-7
• 化学式: C₉₆H₁₂₆O
• 分子量: 1296.06
• InChiKey: ZZDUWSNRXVCVNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  35.9
• 重原子数：
  97
• 可旋转键数：
  39
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-(3-ethoxycarbonylpropyl)-5,8,11,14,17-penta(3,7-dimethyloctanyl)hexa-peri-hexabenzocoronene 在 lithium aluminium tetrahydride 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以85%的产率得到2-(4-hydroxybutyl)-5,8,11,14,17-penta(3,7-dimethyloctanyl)hexa-peri-hexabenzocoronene
  参考文献：
  名称：

  DNA装饰的二维晶体纳米片

  摘要：

  设计和合成表面具有超密集信息丰富分子（如 DNA）阵列的高纵横比 2D 纳米片极具挑战性。在此，我们报告了一种基于两亲性驱动的自组装的通用策略，用于制作高纵横比、表面有 DNA 密集装饰的 2D 片材。显微镜和 X 射线分析表明，这些薄片是结晶的。薄片最独特的特征是 DNA 导向的表面可寻址性，这可以通过序列特异性 DNA 杂交用金纳米粒子装饰薄片的任一面来证明。我们的结果表明，这种设计策略可以作为合成 DNA 装饰高纵横比片的通用方法，这可能会在材料科学、药物输送、

  DOI：

  10.1021/jacs.7b09283

文献信息

• Self-Assembly of Electron Donor−Acceptor Dyads into Ordered Architectures in Two and Three Dimensions:  Surface Patterning and Columnar “Double Cables”
  作者：Paolo Samorì、Xiaomin Yin、Natalia Tchebotareva、Zhaohui Wang、Tadeusz Pakula、Frank Jäckel、Mark D. Watson、Alessandro Venturini、Klaus Müllen、Jürgen P. Rabe

  DOI：10.1021/ja038648+

  日期：2004.3.1

  We report the synthesis and characterization of covalent dyads and multiads of electron acceptors (A) and donors (D), with the purpose of exploiting their nanophase separation behavior toward (a) two-dimensional (2D) surface patterning with well-defined integrated arrays of dissimilar molecular electronic features and (b) bulk self-assembly to noncovalent columnar versions of the so-called "double cable" systems, the likes of which could eventually provide side-by-side percolation pathways for electrons and holes in solar cells. Soluble, alkylated hexa-peri-hexabenzocoronenes (HBCs) bearing tethered anthraquinones (AQs) are shown by scanning tunneling microscopy (STM) to self-assemble at the solution -graphite interface into either defect-rich polycrystalline monolayers or extended 2D crystalline domains, depending on the number of tethered AQs. In the bulk, the thermal stability of the room-temperature HBC columnar phase is increased, which is attributed to the desired nanotriphase separation of HBC columns, insulating alkyl sheaths, and AQ units. Homeotropic alignment (columns normal to surfaces), predicted to be ideal for potential exploitation of such "double cables" in photovoltaic devices, is demonstrated.
• 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.
• DNA-Decorated Two-Dimensional Crystalline Nanosheets
  作者：Shine K. Albert、Irla Sivakumar、Murali Golla、Hari Veera Prasad Thelu、Nithiyanandan Krishnan、Joseph Libin K. L.、Ashish、Reji Varghese

  DOI：10.1021/jacs.7b09283

  日期：2017.12.13

  Design and synthesis of high aspect ratio 2D nanosheets with surface having ultradense array of information-rich molecule such as DNA is extremely challenging. Herein, we report a universal strategy based on amphiphilicity-driven self-assembly for the crafting of high aspect ratio, 2D sheets that are densely surface-decorated with DNA. Microscopy and X-ray analyses have shown that the sheets are crystalline

  设计和合成表面具有超密集信息丰富分子（如 DNA）阵列的高纵横比 2D 纳米片极具挑战性。在此，我们报告了一种基于两亲性驱动的自组装的通用策略，用于制作高纵横比、表面有 DNA 密集装饰的 2D 片材。显微镜和 X 射线分析表明，这些薄片是结晶的。薄片最独特的特征是 DNA 导向的表面可寻址性，这可以通过序列特异性 DNA 杂交用金纳米粒子装饰薄片的任一面来证明。我们的结果表明，这种设计策略可以作为合成 DNA 装饰高纵横比片的通用方法，这可能会在材料科学、药物输送、