2-[4-(2-carboxy-9,10-anthraquinone)-butylate]-5,8,11,14,17-penta-(3,7-dimethyloctanyl)-hexa-peri-hexanenzocoronene

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 2-[4-(2-carboxy-9,10-anthraquinone)-butylate]-5,8,11,14,17-penta-(3,7-dimethyloctanyl)-hexa-peri-hexanenzocoronene
• 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 9,10-dioxoanthracene-2-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 9,10-dioxoanthracene-2-carboxylate
• 化学式: C₁₁₁H₁₃₂O₄
• 分子量: 1530.27
• InChiKey: PTSBULNNGDXFCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  39.3
• 重原子数：
  115
• 可旋转键数：
  42
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  蒽醌-2-羧酸 、 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85%的产率得到2-[4-(2-carboxy-9,10-anthraquinone)-butylate]-5,8,11,14,17-penta-(3,7-dimethyloctanyl)-hexa-peri-hexanenzocoronene
  参考文献：
  名称：

  Self-Assembly of Electron Donor−Acceptor Dyads into Ordered Architectures in Two and Three Dimensions:  Surface Patterning and Columnar “Double Cables”

  摘要：

  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.

  DOI：

  10.1021/ja038648+

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.