9,10-dimethyl-7,12-diphenylbenzo[k]fluoranthene | 253453-56-4

• 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-dimethyl-7,12-diphenylbenzo[k]fluoranthene
• 英文别名: 9,10-Dimethyl-7,12-diphenylbenzo[k]fluoranthene
• CAS: 253453-56-4
• 化学式: C₃₄H₂₄
• 分子量: 432.565
• InChiKey: QSLAJXKBJJSEIK-UHFFFAOYSA-N

物化性质

• 沸点：
  638.5±50.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  9,10-dimethyl-7,12-diphenylbenzo[k]fluoranthene 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 以72%的产率得到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
• 作为产物：
  描述：

  1,2-dibenzoyl-4,5-dimethyl-benzene 在 sodium hydroxide 、 锌 作用下， 以 乙醇 、 xylene 为溶剂， 反应 37.0h， 生成 9,10-dimethyl-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

文献信息

• Synthesis, Structures, and Physical Properties of Benzo[<i>k</i>]fluoranthene-Based Linear Acenes
  作者：Yun-Hua Kung、Yu-Sung Cheng、Chia-Cheng Tai、Wei-Szu Liu、Chien-Chueh Shin、Chih-Chung Ma、Yi-Chan Tsai、Tsun-Cheng Wu、Ming-Yu Kuo、Yao-Ting Wu

  DOI：10.1002/chem.200902695

  日期：2010.5.25

  This work describes the syntheses, crystal structures, photophysical properties, and electro‐chemical analyses of benzo[k]fluoranthene‐based linear acenes, together with ab initio density functional theory computations on them. The molecules were prepared in generally moderate to good yields through Pd‐catalyzed cycloadditions between 1,8‐diethynylnaphthalene derivatives and aryl iodides. This protocol

  这项工作描述了基于苯并[ k ]荧蒽的线性并苯的合成，晶体结构，光物理性质和电化学分析，以及从头开始的密度泛函理论计算。通过在1,8-二乙炔基萘衍生物和芳基碘化物之间进行Pd催化的环加成反应，通常可以以中等到良好的产率制备这些分子。该协议比常规方法更简单，更有效。检查了该反应的范围和局限性。化合物4 hb，15 ac，17 ab，19 ac和24 je的结构通过X射线分析确定; 它们是弯曲的还是扭曲的，而不是平面的。还研究了这些环加合物的光物理和电化学性质，并将其与基于密度泛函理论的计算预测进行了比较。
• Non-doped active layer, benzo[k]fluoranthene-based linear acenes, for deep blue- to green-emissive organic light-emitting diodes
  作者：Yu-Hao Lee、Tsun-Cheng Wu、Chao-Wu Liaw、Ten-Chin Wen、Shih-Wei Feng、Jey-Jau Lee、Yao-Ting Wu、Tzung-Fang Guo

  DOI：10.1016/j.orgel.2013.01.021

  日期：2013.4

  This work studies a series of fluorescent materials, benzo[k]fluoranthene-based linear acenes, and uses these materials directly as the non-doped active layer to fabricate deep blue- to green-emissive organic light emitting diodes (OLEDs). Experimental results indicate that benzo[k]fluoranthene-based linear acenes with different substituents in pristine films have a wide range and strong intensity of the luminescence spectra. The substituents of benzo[k]fluoranthene derivatives modulate the lifetime of the excited state and PL spectra of excitonic, excimer or both emissions in the solid state. Controls of emission spectra are exploited in fabricating high-performance non-doped deep blue to green OLEDs with electroluminescence in the deep blue region (420-460 nm), green region (480-580 nm) or both (430-580 nm). (c) 2013 Elsevier B.V. All rights reserved.
• Photophysical, Electrochemical, and Electrogenerated Chemiluminescent Properties of 9,10-Dimethyl-7,12-diphenylbenzo[<i>k</i>]fluoranthene and 9,10-Dimethylsulfone-7,12-diphenylbenzo[<i>k</i>]fluoranthene
  作者：Eve F. Fabrizio、Andrew Payne、Neil E. Westlund、Allen J. Bard、Philip P. Magnus

  DOI：10.1021/jp012012s

  日期：2002.3.1

  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.