5,8,14,17-tetramesitylhexabenzo[bc,ef,hi,kl,no,qr]coronene-2,11-diol | 1374751-49-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 5,8,14,17-tetramesitylhexabenzo[bc,ef,hi,kl,no,qr]coronene-2,11-diol
• 英文别名: 11,20,34,39-Tetrakis(2,4,6-trimethylphenyl)tridecacyclo[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-diol
• CAS: 1374751-49-1
• 化学式: C₇₈H₅₈O₂
• 分子量: 1027.32
• InChiKey: UIHKHHCULDDKNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23
• 重原子数：
  80
• 可旋转键数：
  4
• 环数：
  17.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,8,14,17-tetramesitylhexabenzo[bc,ef,hi,kl,no,qr]coronene-2,11-diol 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以84%的产率得到5,8,14,17-tetramesitylhexabenzo[bc,ef,hi,kl,no,qr]coronene-1,2,11,12-tetraone
  参考文献：
  名称：

  Synthesis of Oxygen-Substituted Hexa-peri-hexabenzocoronenes through Ir-Catalyzed Direct Borylation

  摘要：

  Direct C-H borylation of hexa-peri-hexabenzocoronenes (HBCs) has been achieved under iridium catalysis, which allows efficient synthesis of hydroxy-substituted HBCs by oxidation of the boryl groups. Further oxidation of dihydroxy HBC with phenyliodine bis(trifluoroacetate) (PIFA) afforded tetraoxo-substituted HBC without any regioisomers, which can be considered as a pi-extended quinone.

  DOI：

  10.1021/ol300743f

文献信息

• Functionalization of Hexa-<i>peri</i>-hexabenzocoronenes: Investigation of the Substituent Effects on a Superbenzene
  作者：Ryuichi Yamaguchi、Satoru Ito、Byung Sun Lee、Satoru Hiroto、Dongho Kim、Hiroshi Shinokubo

  DOI：10.1002/asia.201200723

  日期：2013.1

  high yields. The boryl groups have been transformed into various functionalities such as hydroxy, cyano, ethynyl, and amino groups. We have elucidated that the substituents significantly influence the photophysical properties of HBCs to enhance fluorescence quantum yields. DFT calculations revealed that the origin of the substituent effect is the lift in degeneracy in the frontier orbitals by an interaction

  我们已经证明，六的铱催化直接硼化围-hexabenzocoronene（HBC）使区域选择性引入硼基团与第- ，邻-和元取代高负担国家中高收益。硼基已经转变成各种官能团，例如羟基，氰​​基，乙炔基和氨基。我们已经阐明，取代基显着影响六溴代二苯的光物理性质，以增强荧光量子产率。DFT计算表明，取代基效应的起源是通过与对位和邻位的给电子和吸电子取代基相互作用而使前沿轨道的简并性提升。职位。分子轨道的变化导致从S 0 →S 1状态的跃迁概率增加。另外，对位取代的六溴环十二烷的双光子吸收截面值明显大于邻位和间位取代的六溴环十二烷。