2,11-dibromo-5,8,14,17-tetradodecylhexabenzo[bc,ef,hi,kl,no,qr]coronene | 327604-13-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 2,11-dibromo-5,8,14,17-tetradodecylhexabenzo[bc,ef,hi,kl,no,qr]coronene
• 英文别名: 6,25-Dibromo-11,20,34,39-tetradodecyltridecacyclo[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(15),3,5,7,9,11,13,16(29),17,19,21,23,25,27,30,32,34,36,38,40-henicosaene；6,25-dibromo-11,20,34,39-tetradodecyltridecacyclo[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(15),3,5,7,9,11,13,16(29),17,19,21,23,25,27,30,32,34,36,38,40-henicosaene
• CAS: 327604-13-7
• 化学式: C₉₀H₁₁₂Br₂
• 分子量: 1353.69
• InChiKey: KWHHJWZHLVDZLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  39
• 重原子数：
  92
• 可旋转键数：
  44
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  4,4'-二甲氧基二苯胺 、 2,11-dibromo-5,8,14,17-tetradodecylhexabenzo[bc,ef,hi,kl,no,qr]coronene 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三叔丁基膦 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 以76%的产率得到1,10-bis[di(4'-methoxyphenyl)amino]-4,7,13,16-tetradodecyl-hexa-peri-hexabenzocoronene
  参考文献：
  名称：

  芳胺取代的六-peri-hexabenzocoronenes：简便的合成及其作为“同轴”空穴传输材料的潜在应用。

  摘要：

  DOI：

  10.1002/anie.200460174
• 作为产物：
  描述：

  1,4-Bis(4-bromophenyl)-2,3,5,6-tetrakis(4-dodecylphenyl)benzene 在 硝基甲烷 、 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以87%的产率得到2,11-dibromo-5,8,14,17-tetradodecylhexabenzo[bc,ef,hi,kl,no,qr]coronene
  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

文献信息

• Hydrogen‐Bonded Donor–Acceptor Arrays at the Solution–Graphite Interface
  作者：Gangamallaiah Velpula、Mengmeng Li、Yunbin Hu、Yulian Zagranyarski、Wojciech Pisula、Klaus Müllen、Kunal S. Mali、Steven De Feyter

  DOI：10.1002/chem.201803115

  日期：2018.8.14

  (HBC) derivatives with multiple hydrogen‐bonding (H‐bonding) sites were synthesized and their co‐assembly with alkyl‐substituted perylene tetracarboxy diimide (PDI) was studied using scanning tunneling microscopy (STM) at the solution–graphite interface. STM data shows that electron‐rich HBCs co‐assemble laterally with electron deficient PDIs via preprogrammed H‐bonding sites with high fidelity. The

  控制有机薄膜的纳米级形态是有机（光电）电子器件制造中的关键挑战。（多组分）薄膜的形态又取决于分子组分的相互取向及其在表面上的超分子堆积。此处显示了如何通过（超）分子设计来控制供电子和受电子构件的表面共组装。六围合成了具有多个氢键（H键）位点的六苯并二氢呋喃（HBC）衍生物，并在溶液-石墨界面使用扫描隧道显微镜（STM）研究了它们与烷基取代的per四羧基二酰亚胺（PDI）的共组装。STM数据显示，富电子的HBC通过高保真度的预编程H键结合位点与缺电子的PDI横向组装。通过有机合成改变HBC衍生物上H键位的数量，可以很容易地调节这两种组分的表面化学计量。该模型研究突显了（超）分子设计在与有机电子学相关的构件的组装中的实用性。
• Photomodulation of Two-Dimensional Self-Assembly of Azobenzene–Hexa-<i>peri</i>-hexabenzocoronene–Azobenzene Triads
  作者：Ian Cheng-Yi Hou、Valentin Diez-Cabanes、Agostino Galanti、Michal Valášek、Marcel Mayor、Jérôme Cornil、Akimitsu Narita、Paolo Samorì、Klaus Müllen

  DOI：10.1021/acs.chemmater.9b01535

  日期：2019.9.10

  Achieving exquisite control over self-assembly of functional polycyclic aromatic hydrocarbons (PAH) and nanographene (NG) is essential for their exploitation as active elements in (nano)technological applications. In the framework of our effort to leverage their functional complexity, we designed and synthesized two hexa-peri-hexabenzocoronene (HBC) triads, pAHA and oAHA, decorated with two light-responsive azobenzene moieties at the pseudo-para and ortho positions, respectively. Their photoisomerization in solution is demonstrated by UV–vis absorption. 1H NMR measurements of oAHA suggested 23% of Z-form can be obtained at a photostationary state with UV irradiation (366 nm). Scanning tunneling microscopy imaging revealed that the self-assembly of pAHA and oAHA at the solid–liquid interface between highly oriented pyrolytic graphite (HOPG) and their solution in 1,2,4-trichlorobenzene can be modulated upon light irradiation. This is in contrast to our previous work using HBC bearing a single azobenzene moiety, which did not show such photomodulation of the self-assembled structure. Upon E-Z isomerization both pAHA and oAHA displayed an increased packing density on the surface of graphite. Moreover, pAHA revealed a change of self-assembled pattern from an oblique unit cell to a dimer row rectangular crystal lattice whereas the assembly of oAHA retained a dimer row structure before and after light irradiation, yet with a modification of the inter-row molecular orientation. Molecular mechanics/molecular dynamics simulations validated the self-assembly patterns of pAHA and oAHA, comprising azobenzenes in their Z-forms. These results pave the way toward use of suitably functionalized large PAHs, as well as NGs, to develop photoswitchable devices.

  要将功能性多环芳烃（PAH）和纳米石墨烯（NG）用作（纳米）技术应用中的活性元素，实现对其自组装的精密控制至关重要。为了充分利用它们的功能复杂性，我们设计并合成了两种六全六苯并硼烯（HBC）三元体 pAHA 和 oAHA，它们分别在假对位和正位上装饰有两个光响应偶氮苯分子。紫外-可见吸收证明了它们在溶液中的光异构化。oAHA 的 1H NMR 测量结果表明，在紫外线照射（366 纳米）下，可以获得 23% 的 Z 形光静止态。扫描隧道显微镜成像显示，pAHA 和 oAHA 在高取向热解石墨（HOPG）与它们在 1,2,4- 三氯苯中的溶液之间的固液界面上的自组装可以在光照射下进行调节。这与我们之前使用含有单一偶氮苯分子的 HBC 所做的工作形成了鲜明对比，后者没有显示出自组装结构的这种光调节作用。E-Z 异构化后，pAHA 和 oAHA 在石墨表面的堆积密度都有所增加。此外，pAHA 的自组装模式从斜向单元格转变为二聚体行矩形晶格，而 oAHA 的组装在光照射前后都保留了二聚体行结构，但分子行间取向发生了改变。分子力学/分子动力学模拟验证了 pAHA 和 oAHA 的自组装模式，包括 Z 型偶氮苯。这些结果为利用适当官能化的大型多环芳烃和 NG 开发光开关器件铺平了道路。
• 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.
• Hexa-<i>peri</i>-hexabenzocoronene (HBC)-Incorporated Single- and Double-Stranded Polynorbornenes
  作者：Chih-Wei Chen、Hong-Yi Chang、Shern-Long Lee、I-Jui Hsu、Jey-Jau Lee、Chun-hsien Chen、Tien-Yau Luh

  DOI：10.1021/ma101956n

  日期：2010.11.9

  Double-stranded polymeric ladderphane 1 using HBC as linkers and the single-stranded comblike polynorbornene 2 with HBC pendants are synthesized by the ring-opening metathesis polymerization using the first-generation Grubbs catalyst. The photophysical properties of these HBC-incorporated polymers indicate significant interactions between adjacent polynuclear aromatic chromophores which are comparable with those of aggregated forms of the HBC cores. No liquid crystal properties, however, are observed in these polymers. The STM images of 1 and 2 demonstrate the unique properties of polynorbornene derivatives having N-aryl-5,6-endopyrrolidene pendants or linkers where the polymers are self-assembled to form ordered two-dimensional arrays on the HOPG surface.
• Synthesis and Self-Assembly of Functionalized Hexa-peri-hexabenzocoronenes
  作者：Shunji Ito、Mike Wehmeier、J. Diedrich Brand、Christian Kübel、Rebekka Epsch、Jürgen P. Rabe、Klaus Müllen

  DOI：10.1002/1521-3765(20001201)6:23<4327::aid-chem4327>3.0.co;2-7

  日期：2000.12.1

  iron(III) chloride/nitromethane. Using this strategy three different substitution patterns were synthesized: 2-bromo-5,8,11.14,17-pentadodecylhexa-pecri-hexabenzocoronene (2a), 2,5-dibromo-8,11,14,17-pentadodecylhexa-peri-hexabenzocoronene (2b), and 2,11-dibromo5,8,14,17-pentadodecylhexa-peri-hexa-benzocoronene (2c). These bromo-substituted HBC derivatives were subjected to palladium catalyzed coupling

  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