2-Bromo-5,8,11,14,17-pentadodecylhexa-peri-hexabenzocoronene | 283602-40-4

• 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-pentadodecylhexa-peri-hexabenzocoronene
• 英文别名: 6-Bromo-11,20,25,34,39-pentadodecyltridecacyclo[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: 283602-40-4
• 化学式: C₁₀₂H₁₃₇Br
• 分子量: 1443.11
• InChiKey: PQIVQSFOLLTYGT-UHFFFAOYSA-N

物化性质

• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  43.8
• 重原子数：
  103
• 可旋转键数：
  55
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.59
• 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-pentadodecylhexa-peri-hexabenzocoronene 在 十一烷醇 作用下， 以78%的产率得到
  参考文献：
  名称：

  功能化六邻六苯并芘烯的合成与自组装

  摘要：

  先前已通过扫描隧道显微镜 (STM) 和扫描隧道光谱 (STS) 研究了六邻六苯并可罗烯 (HBC) 1b 的六烷基取代衍生物的单层。预计连接到芳香核的不同官能团（给电子或吸电子）将影响堆积模式，也可能影响电流-电压特性。为了提供合适的模型系统，开发了一种新的合成方法来合成功能化的 HBC 衍生物。这是通过适当溴取代的二苯基乙炔和 2,3,4,5-四芳基环戊二烯-2,4-二烯-1-酮的 [4 + 2]-环加成，然后用氯化铁 (III)/硝基甲烷氧化环脱氢来实现的. 使用该策略合成了三种不同的取代模式：2-bromo-5、8,11.14,17-pentadodecylhexa-pecri-hexabenzocoronene (2a), 2,5-dibromo-8,11,14,17-pentadodecylhexa-peri-hexabenzocoronene (2b), 和 2,11-dibromo5

  DOI：

  10.1002/1521-3765(20001201)6:23<4327::aid-chem4327>3.0.co;2-7
• 作为产物：
  描述：

  4-Bromo-4',4'',4''',4'''',4'''''-pentadodecylhexaphenylbenzene 在 iron(III) chloride 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 1.0h， 以83%的产率得到2-Bromo-5,8,11,14,17-pentadodecylhexa-peri-hexabenzocoronene
  参考文献：
  名称：

  具有不同受体单元的六-邻-六苯并二甲苯，用于调节光电性能

  摘要：

  六围-hexabenzocoronene（HBC）系供体-受体成对用三种不同受体单元合成，通过两种途径：1）“预官能化”之前的环化脱氢单溴取代的六苯基的; 2）环脱氢后单溴取代的六溴环十二烷的“后官能化”。根据附着的受体单元，HBC受体双分子显示出不同程度的分子内电荷转移相互作用，从而可以调节其光物理和光电特性，包括能隙。此处描述的两种合成途径可能是互补的，并且可能适用于合成具有较大芳族核的纳米石墨烯-受体二元组，包括一维延伸的石墨烯纳米带。

  DOI：

  10.1002/asia.201600638

文献信息

• Positive Magneto-LC Effect in Conjugated Spin-Bearing Hexabenzocoronene
  作者：Prince Ravat、Tomasz Marszalek、Wojciech Pisula、Klaus Müllen、Martin Baumgarten

  DOI：10.1021/ja507421x

  日期：2014.9.17

  neutral spin carrying hexabenzocoronene (HBC) derivative is described. The conjugated phenyl nitroxide substituted HBC with five alkyl chains exhibits a positive magneto-LC effect in columnar hexagonal liquid crystalline phase as probed by differential scanning calorimetry and electron paramagnetic resonance spectroscopy. Surprisingly, at 140 K the ΔMS = 2 transition can be observed indicating a thermally

  描述了第一个中性自旋携带六苯并可罗烯 (HBC) 衍生物。通过差示扫描量热法和电子顺磁共振光谱探测，具有五个烷基链的共轭苯基硝基氧取代的 HBC 在柱状六方液晶相中表现出正磁 LC 效应。令人惊讶的是，在 140 K 时，可以观察到 ΔMS = 2 跃迁，表明柱状排列中相邻分子之间存在热可及的三重态。
• Long-Lived Charge Transfer Excited States in HBC-Polypyridyl Complex Hybrids
  作者：Anastasia B. S. Elliott、Raphael Horvath、Xue-Zhong Sun、Michael G. Gardiner、Klaus Müllen、Nigel T. Lucas、Michael W. George、Keith C. Gordon

  DOI：10.1021/acs.inorgchem.5b02602

  日期：2016.5.16

  calculations support the donor–acceptor charge transfer character of these systems, in which HBC is the donor and bpy is the acceptor. The ground state optical properties are dominated by the HBC chromophore with additional distinct transitions of the complexes, one associated with MLCT 450 nm (ε > 17 000 L mol–1 cm–1) and another with a HBC/metal to bpy charge transfer, termed the MLLCT band (373 nm, ε

  报道了用t Bu或C 12 H 25功能化的两个联吡啶-六-周边-六苯并二氢呋喃（bpy-HBC）配体及其Re（I）三羰基氯配合物的合成，并使用光谱和计算方法研究了它们的电子性质。金属配合物表现出不同寻常的性质，我们使用时间分辨红外光谱观察到了长寿命激发态的形成。根据不同的溶剂，这似乎是形式Rebpy的• - HBC •+或以bpy为中心的π，π*状态。TD-DFT计算支持了这些系统的供体-受体电荷转移特性，其中HBC是供体，bpy是受体。基态的光学性质主要由HBC发色团主导，另外还有明显的复合物跃迁，一个跃迁与MLCT 450 nm（ε> 17000 L mol –1 cm –1）有关，另一个与HBC /金属向bpy的电荷转移有关，称为MLLCT谱带（373 nm，ε= 66 000 L mol –1 cm –1）。这些分配也得到共振拉曼光谱的支持。
• Langmuir and Langmuir-Blodgett Films of Amphiphilic Hexa-peri-hexabenzocoronene: New Phase Transitions and Electronic Properties Controlled by Pressure
  作者：Niels Reitzel、Tue Hassenkam、Konstantin Balashev、Torben R. Jensen、Paul B. Howes、Kristian Kjaer、Andreas Fechtenkötter、Natalia Tchebotareva、Shunji Ito、Klaus Müllen、Thomas Bjørnholm

  DOI：10.1002/1521-3765(20011119)7:22<4894::aid-chem4894>3.0.co;2-s

  日期：2001.11.19

  = 71.9 A2 = 3 x 23.9 A2. Thin monolayer films can be transferred to solid supports by the Langmuir-Blodgett (LB) technique. Atomic force microscopy (AFM) with atomic resolution reveals the crystalline packing of alkyl chains in the high-pressure phase. Kelvin force microscopy (KFM) shows a clear potential difference between the high- and low-pressure phases. This is discussed in terms of orbital delocalization

  我们介绍了六烷基六-peri-六苯并并戊二烯（HBC）的两亲衍生物的合成以及结构和电子性质，它含有一个以羧酸基团为末端的烷基取代基。当从溶液在空气-水界面处扩散时，这些分子形成清晰的朗缪尔膜。Langmuir单层的掠入射X射线衍射（GIXD）和X射线反射率研究表明，室温下有两个结晶相，这取决于施加到薄膜上的表面压力。在低压阶段，观察到从高度有序（Zeta = 200-400 A）的pi堆积的HBC分子相对于表面法线倾斜约45度的散射。在此阶段，HBC分子堆积在a = 22.95 A和b = 4.94 A的矩形二维晶胞中。在高压阶段，来自pi堆栈的相干性会丢失。这是由于取代基烷基链结晶成六边形晶格而产生的应力的结果，该六边形晶格在一个方向上具有三聚化的超结构：a = 3 xb = 15.78 A，b = 5.26 A，γ= 120度，A = 71.9 A2 = 3 x 23.9 A2。可以通
• 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.
• Donor–acceptor optoelectronic molecules based on hexa-peri-hexabenzocoronene and benzothiadiazole units: effect of different combinations
  作者：Long Liang、Xue-Qiang Chen、Li-Na Liu、Jun Ling、Xuan Xiang、Wen-Jing Xiao、Cong-Wu Ge、Fu-Gang Zhao、Guanghui Xie、Zhengquan Lu、Jingjing Li、Wei-Shi Li

  DOI：10.1016/j.tet.2016.05.072

  日期：2016.7

  Three donor-acceptor (D-A) conjugated molecules using hexa-peri-hexabenzocoronene (HBC) as D unit while benzo[2,1,3]thiadiazole (BT) as A unit have been synthesized. They have different D-A combination fashions, including D-A, A-D-A and D-A-D. Their thermal, optical, electrochemical properties and molecular interactions have been thoroughly studied, with particular attention paid on the effect of different D-A combinations. Property comparison reveals that the ADA molecule using HBC as core and two BT units as arms possesses a better light absorption property and a more ordered film structure than the other two. Finally, such ADA molecule displayed the best field-effect transistor and photovoltaic performances. (C) 2016 Elsevier Ltd. All rights reserved.