tetrabenzo[a,d,j,m]coronene | 36280-81-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: tetrabenzo[a,d,j,m]coronene
• 英文别名: 1,2:3,4:7,8:9,10-Tetrabenzocoronen；1.2,3.4,7.8,9.10-tetrabenzocoronene；undecacyclo[30.6.2.02,7.08,37.09,14.015,36.018,35.019,24.025,34.026,31.033,38]tetraconta-1(38),2,4,6,8(37),9,11,13,15(36),16,18(35),19,21,23,25(34),26,28,30,32,39-icosaene
• CAS: 36280-81-6
• 化学式: C₄₀H₂₀
• 分子量: 500.599
• InChiKey: UZBGWTCLRMLFQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  40
• 可旋转键数：
  0
• 环数：
  11.0
• 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：

  9,10-bis(diphenylmethylene)-9,10-dihydroanthracene 在 甲烷磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 iron(III) chloride 、 硝基甲烷 作用下， 以 二氯甲烷 为溶剂， 生成 tetrabenzo[a,d,j,m]coronene
  参考文献：
  名称：

  单晶场效应晶体管的扭曲四苯并co衍生物：堆积与迁移率之间的相关性

  摘要：

  合成并表征了一系列在4、7、12、17位上被四个氟，氯或甲基取代的扭曲的四苯并[a，d，j，m]酮（TBC）。除了一个带有甲基取代基的分子，其π-π堆积发生了位移，其余的都显示了π-π界面的堆积，并具有较小的平行位移。对于所有衍生物，在单晶中观察到沿堆叠方向的一维生长。对单晶场效应晶体管的晶体堆积和计算的电子耦合/迁移率与测得的场效应迁移率的系统比较显示出良好的相关性。

  DOI：

  10.1021/cm301190c

文献信息

• 2,3:4,5:8,9:10,11-Tetrabenzoperylene and 1,2:3,4:7,8:9,10-tetrabenzocoronene
  作者：E. Clar、B.A. McAndrew

  DOI：10.1016/0040-4020(72)80174-1

  日期：1972.1

  Tetrabenzoperylene (IV) was synthesized in order to see whether it has fixed double bonds suitable for a double diene synthesis with maleic anhydride. This was found to be the case. From the double adduct (VI) tetrabenzocoronene (VIIIa) was obtained. It cannot have superaromaticity as shown in VIIIb. Attempts to obtain tetrabenzocoronene by photocyclization from IX gave diphenyltribenzopyrene (X).

  合成四苯并per（IV），以查看其是否具有适合与马来酸酐合成双二烯的固定双键。发现情况就是如此。从双加合物（VI）获得四苯并co烯（VIIIa）。如VIIIb所示，它不能具有超芳香性。尝试通过光环化从IX获得四苯并co，得到二苯基三苯并py（X）。
• Skeletal Rearrangement of Twisted Polycyclic Aromatic Hydrocarbons under Scholl Reaction Conditions
  作者：Shunpei Nobusue、Kazuya Fujita、Yoshito Tobe

  DOI：10.1021/acs.orglett.7b01341

  日期：2017.6.16

  3-dichloro-5,6-dicyano-1,4-benzoquinone and scandium trifluoromethanesulfonate) led to stepwise skeletal rearrangements to afford initially a hydrocarbon with a seven-membered ring and then tetrabenzo[a,d,j,m]coronene with all six-membered rings. The course of the rearrangement was interpreted in terms of the acid-catalyzed isomerization of 9,9′-bifluorenylidene into dibenzo[g,p]chrysene moieties on the basis

  在Scholl反应条件下（FeCl 3或2,3-二氯-5,6-二氰基-1,4-苯醌和三氟甲磺酸scan）处理含两个辛酸9,9'-联芴基单元稠合的含环辛酸酯的扭曲多环芳烃逐步地进行骨架重排，首先得到具有七元环的烃，然后得到具有所有六元环的四苯并[ a，d，j，m ] ron烯。在理论研究的基础上，根据9，9′-联芴基的酸催化异构化成二苯并[ g，p ]]部分来解释重排的过程。
• Synthesis, Self-Assembly, and Charge Transporting Property of Contorted Tetrabenzocoronenes
  作者：Xiaojie Zhang、Xiaoxia Jiang、Kai Zhang、Lu Mao、Jing Luo、Chunyan Chi、Hardy Sze On Chan、Jishan Wu

  DOI：10.1021/jo101701k

  日期：2010.12.3

  A facile route has been developed for the preparation of a new family of contorted 1.2,3.4,7.8,9.10-tetrabenzocoronenes (TBCs). A two-step cyclization reaction, i.e., oxidative photocyclization followed by FeCl3-mediated intramolecular cyclodehydrogenation, was carried out on the olefin precursors to obtain the final TBC compounds. These new TBC molecules have contorted conformation due to steric overcrowding as disclosed by single-crystal crystallographic analysis. Nevertheless, they showed extended pi-conjugation compared with coronene and exhibited strong aggregation in solution. The thermal behavior and self-assembly of TBC-C8 in solid were studied by a combination of thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), powder X-ray diffraction (XRD), scanning electron microscope (SEM), and transmission electron microscope (TEM). Compound TBC-C8 showed very good thermal and photostability and exhibited long-range ordered pi-stacking in the bulk state. Moreover, uniform nanofibers with tens of micrometer length are formed in the drop-casted thin films. TBC-C8 also possesses a desirable HOMO energy level (-5.10 eV), which allows efficient charge injection from electrodes such as gold electrode. The charge carrier mobilities were determined by using the space-charge limited-current (SCLC) technique and high average hole mobility of 0.61 cm(2) V-1 s(-1) was obtained for TBC-C8.
• Contorted Tetrabenzocoronene Derivatives for Single Crystal Field Effect Transistors: Correlation between Packing and Mobility
  作者：Someshwar Pola、Chi-Hsien Kuo、Wei-Tao Peng、Md. Minarul Islam、Ito Chao、Yu-Tai Tao

  DOI：10.1021/cm301190c

  日期：2012.7.10

  A series of contorted tetrabenzo[a,d,j,m]coronenes (TBCs) substituted with four fluoro-, chloro-, or methyl groups at 2,7,12,17-positions were synthesized and characterized. Except for the one with methyl substituents, which exhibits a shifted π–π stacking, the rest all show cofacial π–π stacking with small parallel displacements. One-dimensional growth along the stacking direction was observed in

  合成并表征了一系列在4、7、12、17位上被四个氟，氯或甲基取代的扭曲的四苯并[a，d，j，m]酮（TBC）。除了一个带有甲基取代基的分子，其π-π堆积发生了位移，其余的都显示了π-π界面的堆积，并具有较小的平行位移。对于所有衍生物，在单晶中观察到沿堆叠方向的一维生长。对单晶场效应晶体管的晶体堆积和计算的电子耦合/迁移率与测得的场效应迁移率的系统比较显示出良好的相关性。