六苯并[a,d,g,j,m,p]晕苯 | 1065-80-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 中文名称: 六苯并[a,d,g,j,m,p]晕苯
• 英文名称: hexabenzocoronene
• 英文别名: 1,2:3,4:5,6:7,8:9,10:11,12-Hexabenzocoronen；HBC；Hexabenzo[a,d,g,j,m,p]coronene；tridecacyclo[34.6.6.02,7.08,41.09,14.015,40.016,21.022,39.023,28.029,38.030,35.037,42.043,48]octatetraconta-1(42),2,4,6,8(41),9,11,13,15(40),16,18,20,22(39),23,25,27,29(38),30,32,34,36,43,45,47-tetracosaene
• CAS: 1065-80-1
• 化学式: C₄₈H₂₄
• 分子量: 600.719
• InChiKey: XHJPOZDMDBETDO-UHFFFAOYSA-N

物化性质

• 熔点：
  516 °C
• 密度：
  1.467±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.2
• 重原子数：
  48
• 可旋转键数：
  0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1,3,5-tris(2'-biphenyl)ylbenzene 在 iron(III) chloride 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 1.0h， 以86.1%的产率得到六苯并[a,d,g,j,m,p]晕苯
  参考文献：
  名称：

  胺和三氟乙酸催化的芳基甲基酮的三重缩合：在温和条件下可直接与1,3,5-三芳基苯接触

  摘要：

  报道了乙二胺和三氟乙酸催化的芳基甲基酮的有效三重缩合反应。以良好至优异的产率获得了广泛的1,3,5-三芳基苯。该反应为在温和条件下接触多环芳烃的有机材料提供了一种新颖而实用的方法。

  DOI：

  10.1016/j.tetlet.2012.03.008

文献信息

• The synthesis of 1:2, 3:4, 5:6, 7:8, 9:10, 11:12-hexabenzocoronene
  作者：E. Clar、J.F. Stephen

  DOI：10.1016/s0040-4020(01)82216-x

  日期：1965.1

  The acid (1) was condensed with phthalic anhydride to the dicarboxylic acid (II). One sided cyclization yielded the acid (III) which was reduced to (IV). A second cyclization gave the pentacene derivative (V) which was oxidized to the diquinone (VI). Compound VI reacted with phenyl lithium to form the tetraol (VII) which was condensed to hexabenzocoronene (VIII) by heating with copper powder.

  将酸（1）与邻苯二甲酸酐缩合为二羧酸（II）。单侧环化产生酸（III），其被还原为（IV）。第二次环化得到并五苯衍生物（V），其被氧化为二醌（VI）。化合物VI与苯基锂反应形成四元醇（VII），通过与铜粉加热将其缩合为六苯并二氢呋喃（VIII）。
• Molecular Wires from Contorted Aromatic Compounds
  作者：Shengxiong Xiao、Matthew Myers、Qian Miao、Sébastien Sanaur、Keliang Pang、Michael L. Steigerwald、Colin Nuckolls

  DOI：10.1002/anie.200502142

  日期：2005.11.18
• Polysubstituted Hexa-cata-hexabenzocoronenes: Syntheses, Characterization, and Their Potential as Semiconducting Materials in Transistor Applications
  作者：Sushil Kumar、Someshwar Pola、Chih-Wei Huang、Md. Minarul Islam、Samala Venkateswarlu、Yu-Tai Tao

  DOI：10.1021/acs.joc.9b00802

  日期：2019.7.5

  A series of tetra- and octa-substituted hexa-cata-hexabenzocoronenes (cata-HBCs) were synthesized from tetraryl olefins via iodine- and iron chloride-catalyzed oxidative cyclodehydrogenation reactions. The substitutions on the periphery of the parent HBC serve to modify the photophysical properties, highest occupied molecular orbital-lowest unoccupied molecular orbital gaps, and thermal stabilities of the respective derivatives. The crystal structures were determined to display multiple twists in the framework, resulting in different packing motifs depending on the position, type, and number of functional groups on the hexabenzocoronene framework. Nearly perfect co-facial packing to marginally or extensively shifted co-facial stacks were obtained due to substitution. The single crystals of parent HBC were used to fabricate single-crystal field-effect transistors, from which the highest p-channel mobility of 0.51 cm² V^-1 s^-1 was measured. Thin-film transistors of selected HBCs were also prepared, and 0.61 cm² V^-1 s^-1 was obtained for MeHBC-2. These results attest the potential of these materials as semiconducting materials.
• Triple condensation of aryl methyl ketones catalyzed by amine and trifluoroacetic acid: straightforward access to 1,3,5-triarylbenzenes under mild conditions
  作者：Shao-Liang Zhang、Zhao-Feng Xue、Ya-Ru Gao、Shuai Mao、Yong-Qiang Wang

  DOI：10.1016/j.tetlet.2012.03.008

  日期：2012.5

  An efficient triple condensation reaction of aryl methyl ketones catalyzed by ethylenediamine and trifluoroacetic acid was reported. A broad scope of 1,3,5-triarylbenzenes was obtained in good to excellent yields. The reaction provides a novel and practical approach to access organic materials of polycyclic aromatic hydrocarbons under mild conditions.

  报道了乙二胺和三氟乙酸催化的芳基甲基酮的有效三重缩合反应。以良好至优异的产率获得了广泛的1,3,5-三芳基苯。该反应为在温和条件下接触多环芳烃的有机材料提供了一种新颖而实用的方法。