二苯并[a,o]苝 | 190-36-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 二苯并[a,o]苝
• 英文名称: helianthrene
• 英文别名: dibenzo[a,o]perylene；Dibenzo[a,o]perylen；Dibenzo-perylen；1,2,11,12-Dibenzo-perylen；1,2:11,12-Dibenzoperylen；1,2;11,12-Dibenz-perylen；Dibenzo[a,o]perylene；heptacyclo[13.11.1.12,10.03,8.019,27.021,26.014,28]octacosa-1(27),2(28),3,5,7,9,11,13,15,17,19,21,23,25-tetradecaene
• CAS: 190-36-3
• 化学式: C₂₈H₁₆
• 分子量: 352.435
• InChiKey: PYTPIODZIPXLKF-UHFFFAOYSA-N

物化性质

• 沸点：
  629.3±22.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  7.0
• 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

安全信息

• 海关编码：
  2902909090

反应信息

• 作为反应物：
  描述：

  二苯并[a,o]苝 在 氧气 作用下， 以 甲苯 为溶剂， 生成 7H-7,11b-epidioxydibenzo[a,o]perylene
  参考文献：
  名称：

  Endoperoxide formation of helianthrene with triplet molecular oxygen. A spin-forbidden reaction

  摘要：

  Dibenzo[a,o]perylene (helianthrene = HEL), known to be a very reactive singlet molecular oxygen (O-1(2), 1-DELTA-g) acceptor, also reacts with molecular oxygen in its triplet ground state (O-3(2), 3-SIGMA(g)-) to form helianthrene endoperoxide (HELPO). The thermal endoperoxide formation was studied in several solvents at r m temperature. In nonpolar solvents such as toluene and carbon disulfide the temperature-dependent equilibrium, HEL + O-3(2) reversible HELPO, is established by the thermolysis of HELPO even at low temperatures. Kinetic parameters for the HELPO formation in toluene are DELTA-H double dagger = 10.2 +/- 1.0 kcal mol-1 and DELTA-S double dagger = -39 +/- 5 eu, indicating that O-1(2) is not involved in the reaction pathway. This is the first example of aromatic endoperoxide formation by reaction with molecular oxygen in its ground state.

  DOI：

  10.1021/ja00038a007
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium chloride 、 zinc(II) chloride 、 锌 作用下， 生成 二苯并[a,o]苝
  参考文献：
  名称：

  Brockmann et al., Justus Liebigs Annalen der Chemie, 1942, vol. 553, p. 1;

  摘要：

  DOI：

文献信息

• Organic electroluminescent device
  申请人：NEC Corporation

  公开号：US06465116B1

  公开（公告）日：2002-10-15

  An organic electroluminescent (EL) device includes one or more organic thin film layers disposed between an anode and a cathode, at least one of said layers containing, in a form of a mixture or a single substance, a pentacene compound expressed in Formula 1, a dibenzoperylene compound expressed in Formula 3 or another dibenzoperylene compound expressed in Formula 4. The organic EL device exhibits higher luminance than that obtained by a conventional organic EL device.

  一种有机电致发光（EL）器件包括一个阳极和一个阴极之间放置的一个或多个有机薄膜层，其中至少一个层包含以混合物或单一物质形式表达的五环芘化合物（公式1）、二苯并芘化合物（公式3）或另一种二苯并芘化合物（公式4）。该有机EL器件显示出比传统有机EL器件获得的更高亮度。
• Brockmann et al., Justus Liebigs Annalen der Chemie, 1942, vol. 553, p. 1;
  作者：Brockmann et al.

  DOI：——

  日期：——
• Clar,E., Polycyclic Hydrocarbons Bd. 2 <London 1964> S. 48
  作者：Clar,E.

  DOI：——

  日期：——
• Clar, Chemische Berichte, 1949, vol. 82, p. 46,55, 59
  作者：Clar

  DOI：——

  日期：——
• Endoperoxide formation of helianthrene with triplet molecular oxygen. A spin-forbidden reaction
  作者：M. Seip、H. D. Brauer

  DOI：10.1021/ja00038a007

  日期：1992.6

  Dibenzo[a,o]perylene (helianthrene = HEL), known to be a very reactive singlet molecular oxygen (O-1(2), 1-DELTA-g) acceptor, also reacts with molecular oxygen in its triplet ground state (O-3(2), 3-SIGMA(g)-) to form helianthrene endoperoxide (HELPO). The thermal endoperoxide formation was studied in several solvents at r m temperature. In nonpolar solvents such as toluene and carbon disulfide the temperature-dependent equilibrium, HEL + O-3(2) reversible HELPO, is established by the thermolysis of HELPO even at low temperatures. Kinetic parameters for the HELPO formation in toluene are DELTA-H double dagger = 10.2 +/- 1.0 kcal mol-1 and DELTA-S double dagger = -39 +/- 5 eu, indicating that O-1(2) is not involved in the reaction pathway. This is the first example of aromatic endoperoxide formation by reaction with molecular oxygen in its ground state.