1,2,3,4,5-pentakis(4-bromophenyl)-6-phenylbenzene | 1542081-48-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2,3,4,5-pentakis(4-bromophenyl)-6-phenylbenzene
• 英文别名: 1,2,3,4,5-Pentakis(4-bromophenyl)-6-phenylbenzene
• CAS: 1542081-48-0
• 化学式: C₄₂H₂₅Br₅
• 分子量: 929.18
• InChiKey: BQCKJTVJDJNWDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.5
• 重原子数：
  47.0
• 可旋转键数：
  6.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1,2,3,4,5-pentakis(4-bromophenyl)-6-phenylbenzene 、 magnesium,1,3,5-trimethylbenzene-6-ide,bromide 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 di-tert-butylphosphine oxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以95%的产率得到1,2,3,4,5-pentakis(4-mesitylphenyl)-6-phenylbenzene
  参考文献：
  名称：

  明亮的合成红色发射dicyanoetheno-桥六围-hexabenzocoronene二聚体†

  摘要：

  引入二氰甲基阴离子基团与六围-hexabenzocoronene（HBC）显着增强HBC的发射特性由于大的扰动其电子结构的。另外，由二氰甲基甲基HBC阴离子的氧化获得的双氰基-氨基桥接的HBC二聚体在溶液和固态下显示亮红色发射。HBC单元和双氰基乙烯桥之间的分子内电荷转移相互作用在其发射光谱中引起溶剂变色行为。Dicyanoetheno桥联二聚体HBC表现出顺式-反式中的溶液行为光致异构化，在该混合物中，得到顺式-异构体显性的光稳态。理论计算表明顺式异构体比反式异构体在热力学上更稳定。

  DOI：

  10.1039/c6ob02775j
• 作为产物：
  描述：

  2,3,4,5-tetrakis(4-bromophenyl)cyclopenta-2,4-dienone 、 1-溴-4-(苯基乙炔基)苯 以 二苯醚 为溶剂， 以84%的产率得到1,2,3,4,5-pentakis(4-bromophenyl)-6-phenylbenzene
  参考文献：
  名称：

  Selective Alternate Derivatization of the Hexaphenylbenzene Framework through a Thermodynamically Controlled Halogen Dance

  摘要：

  We report a practical synthetic protocol and mechanistic details for the selective alternate derivatization of the hexaphenylbenzene (HPB) framework through a thermodynamically controlled halogen dance. The stability of the alternately trilithiated species of HPB is interpreted by the through-space interaction at the ipso-carbons of the phenyl groups of the HPB framework. By using this approach, C-3-symmetric and lower-symmetric HPB derivatives possessing two or three kinds of substituents on the periphery have become easily and practically available.

  DOI：

  10.1021/ol500041j

文献信息

• Mesityllithium and p-(dimethylamino)phenyllithium for the selective alternate trilithiation of the hexaphenylbenzene framework
  作者：Tatsuo Kojima、Shuichi Hiraoka

  DOI：10.1039/c4cc04520c

  日期：——

  We report mesityllithium and p-(dimethylamino)phenyllithium as new valuable lithiating reagents, which realize Br/Li exchange reaction of bromoarenes at relatively high temperature in THF. With these reagents, we established the general and practical protocols for the selective alternate trilithiation of the hexaphenylbenzene framework.

  我们报道了异丁基锂和对-（二甲基氨基）苯基锂作为新的有价值的锂化试剂，它们在较高温度下在THF中实现溴芳烃的Br / Li交换反应。用这些试剂，我们建立了六苯基苯骨架选择性交替三锂化的通用和实用方案。
• Selective Alternate Derivatization of the Hexaphenylbenzene Framework through a Thermodynamically Controlled Halogen Dance
  作者：Tatsuo Kojima、Shuichi Hiraoka

  DOI：10.1021/ol500041j

  日期：2014.2.7

  We report a practical synthetic protocol and mechanistic details for the selective alternate derivatization of the hexaphenylbenzene (HPB) framework through a thermodynamically controlled halogen dance. The stability of the alternately trilithiated species of HPB is interpreted by the through-space interaction at the ipso-carbons of the phenyl groups of the HPB framework. By using this approach, C-3-symmetric and lower-symmetric HPB derivatives possessing two or three kinds of substituents on the periphery have become easily and practically available.
• Synthesis of bright red-emissive dicyanoetheno-bridged hexa-peri-hexabenzocoronene dimers
  作者：Kazuma Oda、Satoru Hiroto、Ichiro Hisaki、Hiroshi Shinokubo

  DOI：10.1039/c6ob02775j

  日期：——

  The introduction of a dicyanomethyl anion group to hexa-peri-hexabenzocoronene (HBC) substantially enhanced the emission properties of HBC due to a large perturbation of its electronic structure. In addition, dicyanoetheno-bridged HBC dimers obtained from oxidation of a dicyanomethyl HBC anion exhibited bright red emission in solution and solid states. Intramolecular charge transfer interactions between

  引入二氰甲基阴离子基团与六围-hexabenzocoronene（HBC）显着增强HBC的发射特性由于大的扰动其电子结构的。另外，由二氰甲基甲基HBC阴离子的氧化获得的双氰基-氨基桥接的HBC二聚体在溶液和固态下显示亮红色发射。HBC单元和双氰基乙烯桥之间的分子内电荷转移相互作用在其发射光谱中引起溶剂变色行为。Dicyanoetheno桥联二聚体HBC表现出顺式-反式中的溶液行为光致异构化，在该混合物中，得到顺式-异构体显性的光稳态。理论计算表明顺式异构体比反式异构体在热力学上更稳定。