9,10-bis(bromomethyl)-7,12-diphenylbenzo[k]fluoranthene | 393587-02-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 9,10-bis(bromomethyl)-7,12-diphenylbenzo[k]fluoranthene
• CAS: 393587-02-5
• 化学式: C₃₄H₂₂Br₂
• 分子量: 590.357
• InChiKey: QDPWPYRERCCEBT-UHFFFAOYSA-N

物化性质

• 沸点：
  707.7±55.0 °C(Predicted)
• 密度：
  1.530±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.76
• 重原子数：
  36.0
• 可旋转键数：
  4.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  9,10-bis(bromomethyl)-7,12-diphenylbenzo[k]fluoranthene 在 sodium sulfide 、 4 A molecular sieve 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以94%的产率得到
  参考文献：
  名称：

  Photophysical, Electrochemical, and Electrogenerated Chemiluminescent Properties of 9,10-Dimethyl-7,12-diphenylbenzo[k]fluoranthene and 9,10-Dimethylsulfone-7,12-diphenylbenzo[k]fluoranthene

  摘要：

  A newly synthesized light emitting compound 9,10-dimethylsulfone-7,12-diphenylbenzo[k]fluoranthene (DSDPBF) and its synthetic intermediate 9, 10-dimethyl-7,12-diphenylbenzo[k] fluoranthene (DMDPBF) were studied to evaluate how the addition of weak electron donating methyl groups and the subsequent addition of an electron withdrawing sulfone group affect the photophysical and electrochemical properties as well as the rate of radical cation coupling of the parent compound, 7,12-diphenylbenzo[k]fluoranthene (DPBF). Although the photochemical and electrochemical properties of DSDPBF were more similar to the unsubstituted DPBF than to the DMDPBF, there was a substantial decrease in the quantum efficiency upon addition of the electron-rich sulfone group which was not observed upon addition of the methyl groups. On the other hand, the rate of radical cation coupling or dimerization observed upon electrochemical oxidation varied significantly. The addition of the electron donating methyl groups decreased the reactivity of the radical cation resulting in a 40 times slower rate of dimerization than that observed for the unsubstituted benzo[k]fluoranthene, whereas the addition of the electron withdrawing sulfone group to the methyl groups increased the radical cation reactivity resulting in a rate of dimerization that was 3 times faster than the unsubstituted parent compound. As a result, the electrogenerated chemiluininescence emission spectrum obtained from the annihilation reaction between the radical anion and radical cations of DSDPBF was dominated by emission from the dimer at 589 and 621 nm instead of emission from the monomer at ca. 485 nm.

  DOI：

  10.1021/jp012012s
• 作为产物：
  描述：

  5,6-二甲基-1,3-二苯基-2-苯并呋喃 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 xylene 为溶剂， 反应 41.0h， 生成 9,10-bis(bromomethyl)-7,12-diphenylbenzo[k]fluoranthene
  参考文献：
  名称：

  Photophysical, Electrochemical, and Electrogenerated Chemiluminescent Properties of 9,10-Dimethyl-7,12-diphenylbenzo[k]fluoranthene and 9,10-Dimethylsulfone-7,12-diphenylbenzo[k]fluoranthene

  摘要：

  A newly synthesized light emitting compound 9,10-dimethylsulfone-7,12-diphenylbenzo[k]fluoranthene (DSDPBF) and its synthetic intermediate 9, 10-dimethyl-7,12-diphenylbenzo[k] fluoranthene (DMDPBF) were studied to evaluate how the addition of weak electron donating methyl groups and the subsequent addition of an electron withdrawing sulfone group affect the photophysical and electrochemical properties as well as the rate of radical cation coupling of the parent compound, 7,12-diphenylbenzo[k]fluoranthene (DPBF). Although the photochemical and electrochemical properties of DSDPBF were more similar to the unsubstituted DPBF than to the DMDPBF, there was a substantial decrease in the quantum efficiency upon addition of the electron-rich sulfone group which was not observed upon addition of the methyl groups. On the other hand, the rate of radical cation coupling or dimerization observed upon electrochemical oxidation varied significantly. The addition of the electron donating methyl groups decreased the reactivity of the radical cation resulting in a 40 times slower rate of dimerization than that observed for the unsubstituted benzo[k]fluoranthene, whereas the addition of the electron withdrawing sulfone group to the methyl groups increased the radical cation reactivity resulting in a rate of dimerization that was 3 times faster than the unsubstituted parent compound. As a result, the electrogenerated chemiluininescence emission spectrum obtained from the annihilation reaction between the radical anion and radical cations of DSDPBF was dominated by emission from the dimer at 589 and 621 nm instead of emission from the monomer at ca. 485 nm.

  DOI：

  10.1021/jp012012s