2-bromo-5,8,11,14,17-penta(3,7-dimethyloctanyl)-hexa-peri-hexabenzocoronene | 347390-08-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 2-bromo-5,8,11,14,17-penta(3,7-dimethyloctanyl)-hexa-peri-hexabenzocoronene
• 英文别名: 6-Bromo-11,20,25,34,39-pentakis(3,7-dimethyloctyl)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-1,3,5,7,9,11,13,15,17(22),18,20,23,25,27(32),28,30,33,35,37(42),38,40-henicosaene
• CAS: 347390-08-3
• 化学式: C₉₂H₁₁₇Br
• 分子量: 1302.84
• InChiKey: JIHJJWYIXABNOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  35.5
• 重原子数：
  93
• 可旋转键数：
  35
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  2-bromo-5,8,11,14,17-penta(3,7-dimethyloctanyl)-hexa-peri-hexabenzocoronene 在 2,2'-联吡啶 、 1,5-cis,cis-cyclooctadiene 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以87%的产率得到6,11,20,25,34-Pentakis(3,7-dimethyloctyl)-39-[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-1,3,5,7,9,11,13,15,17(22),18,20,23,25,27(32),28,30,33,35,37(42),38,40-henicosaenyl]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(30),2(15),3(8),4,6,9,11,13,16,18,20,22,24,26,28,31,33,35,37(42),38,40-henicosaene
  参考文献：
  名称：

  Oligomers of Hexa-peri-hexabenzocoronenes as “Super-oligophenylenes”:  Synthesis, Electronic Properties, and Self-assembly

  摘要：

  Hexa-peri-hexabenzocoronene (HBC) is a remarkable polycyclic aromatic hydrocarbon and is often called "superbenzene" because of its similarity to benzene. In this article we present the facile synthesis of oligomers of HBC, up to trimers (3, 4, 5a-c) with different modes of connection. UV-vis and fluorescence spectroscopy studies reveal that the oligomers are electronically decoupled. This arises from the small atomic orbital coefficients of the bridge-head carbon atoms, the large torsion angle between the HBC units, and the large distance of interacting transition dipoles due to the size of the HBC chromophore. For comparison, a methylene-bridged HBC dimer 6, so-called "superfluorene", was prepared. The induced planarity improves pi-conjugation and suppresses the geometrical relaxation of the backbone upon electronic excitation, leading to a prominent 0-0 transition band in the fluorescence spectra. The self-assembly of the oligomers and of superfluorene 6 was studied by wide-angle X-ray diffraction (WAXD) in the bulk state, and ordered columnar stacking occurs in the HBC dimer 3, p-HBC trimer 4, and superfluorene 6. Measurements of shear-aligned samples show that, despite increasing aspects ratio by linear entrainment of disks, the anitropic element that is subject to alignment by shear is the supramolecular columns.

  DOI：

  10.1021/jo0490301
• 作为产物：
  描述：

  1-(4-bromophenyl)-2,3,4,5,6-pentakis(3,7-dimethyloctanylphenyl)benzene 在 iron(III) chloride 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 4.0h， 以70%的产率得到2-bromo-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

• Reinforced Self-Assembly of Hexa-<i>peri</i>-hexabenzocoronenes by Hydrogen Bonds: From Microscopic Aggregates to Macroscopic Fluorescent Organogels
  作者：Xi Dou、Wojciech Pisula、Jishan Wu、Graham J. Bodwell、Klaus Müllen

  DOI：10.1002/chem.200700921

  日期：2008.1

  intracolumnar hydrogen bonds on the self-assembly behavior of HBCs. The hydrogen bonds effectively increased the aggregation tendency of these compounds in solution. In the bulk state, the typical columnar supramolecular arrangement of HBCs was either stabilized substantially (1 a, 1 b, 2 a, and 2 b), or suppressed by dominant hydrogen-bonding interactions (3). For some of the compounds (1 a, 2 a, and

  已经合成了具有与芳族核相邻的氢键合官能团（酰胺基或脲基）的六-peri-六苯并二氢呋喃衍生物（HBC），以研究柱内氢键对HBCs自组装行为的影响。氢键有效地增加了这些化合物在溶液中的聚集趋势。在本体状态下，典型的HBC圆柱状超分子排列要么基本稳定（1a，1b，2a和2b），要么被主要的氢键相互作用所抑制（3）。对于某些化合物（1a，2a和2b），在退火后，即使在液晶状态下采用的超分子排列也得以保留，这可能是由于氢键增强了pi堆积相互作用。此外，
• Discotic liquid crystalline hexabenzocoronenes carrying chiral and racemic branched alkyl chains: supramolecular engineering and improved synthetic methods
  作者：Andreas Fechtenkötter、Natalia Tchebotareva、Mark Watson、Klaus Müllen

  DOI：10.1016/s0040-4020(01)00252-6

  日期：2001.4

  In this paper we present the synthesis and characterization of three different thermotropic liquid crystalline derivatives of hexabenzocoronene (HBC), substituted at the periphery by six chiral or racemic branched (3,7-dimethyloctanyl) chains, namely the chiral 5a, racemic 5b, and mono-bromo functionalized 18 carrying five alkyl chains. Improved methods for synthesis of HBC precursors, largely relying

  在本文中，我们介绍了三种不同的六苯并二苯并（HBC）的热致液晶衍生物的合成和表征，它们在外围被六个手性或外消旋的分支（3,7-二甲基辛基）链取代，即手性5a，外消旋5b和具有五个烷基链的单溴官能化18。还描述了主要依靠过渡金属催化的偶联反应合成HBC前体的改进方法。相对于载有n的类似HBC，当K→D H的热转变转变为更低的温度时，溶解度和可加工性得到了提高-烷基链。在被手性支链烷基链5a取代的情况下，已经通过圆二色光谱法记录了强信号。所有新化合物均通过1 H，13 C NMR，UV-Vis光谱和FD-MS表征。初步的中间相表征是通过差示扫描量热法（DSC）和偏振光显微镜进行的。在DSC实验过程中，对光学纯和外消旋HBC衍生物进行了比较。
• Synthesis and Controlled Self-Assembly of Covalently Linked Hexa-<i>peri</i>-hexabenzocoronene/Perylene Diimide Dyads as Models To Study Fundamental Energy and Electron Transfer Processes
  作者：Lukas F. Dössel、Valentin Kamm、Ian A. Howard、Frédéric Laquai、Wojciech Pisula、Xinliang Feng、Chen Li、Masayoshi Takase、Tibor Kudernac、Steven De Feyter、Klaus Müllen

  DOI：10.1021/ja211504a

  日期：2012.4.4

  We report the synthesis and photophysical characterization of a series of hexa-peri-hexabenzocoronene (HBC)/perylenetetracarboxy diimide (PDI) dyads that are covalently linked with a rigid bridge. Both the ratio of the two components and the conjugation of the bridging element are systematically modified to study the influence on self-assembly and energy and electron transfer between electron donor

  我们报告了一系列与刚性桥共价连接的六对六苯并可罗烯 (HBC)/苝四羧基二亚胺 (PDI) 二元组的合成和光物理表征。系统地修改了两种组分的比例和桥接元素的共轭，以研究对电子供体 HBC 和受体 PDI 之间自组装和能量和电子转移的影响。STM 和 2D-​​WAXS 实验表明，无论是在溶液中还是在块状固态中，二元组都组装成有序的二维超分子结构，在纳米尺度上，供体和受体之间的相互方向和距离可控。根据二元组的对称性，观察到具有 HBC 和 PDI 纳米隔离堆叠的柱子或具有交替 HBC 和 PDI 部分的交叉网络。UV-vis、光致发光、瞬态光致发光和瞬态吸收光谱证实，在供体 HBC 光激发后，HBC 和 PDI 之间的光诱导电子转移只能与主要的 Förster 共振能量转移竞争，如果通过 HBC 和 PDI 的紧密堆叠促进有足够的轨道重叠。然而，虽然交替堆叠允许有效的电子转移，但只有纳米隔离
• Self-Assembly, Molecular Dynamics, and Kinetics of Structure Formation in Dipole-Functionalized Discotic Liquid Crystals
  作者：Mahdy M. Elmahdy、Xi Dou、Mihail Mondeshki、George Floudas、Hans-Jürgen Butt、Hans W. Spiess、Klaus Müllen

  DOI：10.1021/ja7113618

  日期：2008.4.1

  The self-assembly, the molecular dynamics, and the kinetics of structure formation are studied in dipole-functionalized hexabenzocoronene (HBC) derivatives. Dipole substitution destabilizes the columnar crystalline phase except for the dimethoxy- and monoethynyl-substituted HBCs that undergo a reversible transformation to the crystalline phase. The disk dynamics are studied by dielectric spectroscopy and site-specific NMR techniques that provide both the time-scale and geometry of motion. Application of pressure results in the thermodynamic phase diagram that shows increasing stability of the crystalline phase at elevated pressures. Long-lived metastability was found during the transformation between the two phases. These results suggest new thermodynamic and kinetic pathways that favor the phase with the highest charge carrier mobility.
• Hexa-peri-hexabenzocoronene/perylenedicarboxymonoimide and diimide dyads as models to study intramolecular energy transfer
  作者：Jishan Wu、Jianqiang Qu、Natalia Tchebotareva、Klaus Müllen

  DOI：10.1016/j.tetlet.2004.12.094

  日期：2005.2

  Star-like and butterfly-shaped dyads based on hexa-peri-hexabenzocoronene (HBC) as donor and perylenedicarboxymoniimide (PMI) or diimide (PDI) as acceptor were synthesized by Sonogashira coupling reactions and Diels-Alder cycloadditions. Intramolecular energy and electron transfer were investigated by steady-state fluorescence spectroscopy. (C) 2004 Elsevier Ltd. All rights reserved.