3,10-Diphenyl-1,2:4,5:8,9-tribenzopyren | 36280-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 3,10-Diphenyl-1,2:4,5:8,9-tribenzopyren
• 英文别名: 9,26-Diphenylheptacyclo[14.10.2.02,7.08,28.010,15.019,27.020,25]octacosa-1(26),2,4,6,8,10,12,14,16(28),17,19(27),20,22,24-tetradecaene
• CAS: 36280-83-8
• 化学式: C₄₀H₂₄
• 分子量: 504.631
• InChiKey: PMJHPDNMYYYHDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  40
• 可旋转键数：
  2
• 环数：
  9.0
• 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

• 作为反应物：
  描述：

  3,10-Diphenyl-1,2:4,5:8,9-tribenzopyren 在 iron(III) chloride 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 0.42h， 以57%的产率得到tetrabenzo[a,d,j,m]coronene
  参考文献：
  名称：

  Synthesis, Self-Assembly, and Charge Transporting Property of Contorted Tetrabenzocoronenes

  摘要：

  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.

  DOI：

  10.1021/jo101701k
• 作为产物：
  描述：

  9,10-bis(diphenylmethylene)-9,10-dihydroanthracene 以 苯 为溶剂， 生成 3,10-Diphenyl-1,2:4,5:8,9-tribenzopyren
  参考文献：
  名称：

  2,3：4,5：8,9：10,11-四苯并per和1,2：3,4：7,8：9,10-四苯并ron

  摘要：

  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）。

  DOI：

  10.1016/0040-4020(72)80174-1

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）。
• 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.