2,5-diphenyl-3,4-bis[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopenta-2,4-dien-1-one | 866393-60-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2,5-diphenyl-3,4-bis[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopenta-2,4-dien-1-one
• 英文别名: 3,4-bis(4-(4,4,5,5-tetramethyl-1,3-dioxaborolan-2-yl)phenyl)-2,5-diphenylcyclopenta-2,4-dien-1-one；3,4-bis[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2,5-diphenylcyclopenta-2,4-dienone；3,4-bis[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2,5-diphenylcyclopentadienone；2,5-Diphenyl-3,4-bis[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopenta-2,4-dien-1-one
• CAS: 866393-60-4
• 化学式: C₄₁H₄₂B₂O₅
• 分子量: 636.403
• InChiKey: BNHJRQVNGMVXPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.39
• 重原子数：
  48
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-diphenyl-3,4-bis[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopenta-2,4-dien-1-one 、 2-(4-溴苯基)-5-(4-叔丁基苯基)-1,3,4-恶二唑 在 四(三苯基膦)钯 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 48.0h， 以86.6%的产率得到
  参考文献：
  名称：

  具有双极性电荷传输部分的蓝色发光聚苯撑树状聚合物。

  摘要：

  合成并表征了具有空穴和电子传输部分的两种发光聚苯撑树枝状聚合物。当在非极性环境中表征时，这两种分子都仅从core核中表现出纯蓝色发射，并且表面到核的能量转移效率很高。特别是，咔唑和恶二唑官能化的树枝状聚合物（D1）在极性增加的环境中表现出从from核发出的纯蓝色发射，而未显示分子内电荷转移（ICT）。另一方面，在高极性溶剂中，三苯胺和恶二唑官能化的化合物（D2）表现出显着的ICT，其核心和ICT态都有双重发射。D1，在三层有机发光二极管（OLED）中通过溶液处理通过国际佣金委员会（de Commission Internationale de l' Éclairage1931 CIE xy =（0.16，0.12），峰值电流效率为0.21 cd / A，峰值亮度为2700 cd /m²。这代表了第一个报道的纯蓝色树枝状大分子发射体，其在OLED中具有双极性电荷传输和表面到核心的能量转移。

  DOI：

  10.3390/molecules21101400
• 作为产物：
  描述：

  3,4-bis-(4-bromo-phenyl)-2,5-diphenyl-cyclopentadienone 、 联硼酸频那醇酯 在 [Pd⁰(1,1’-bis(diphenylphosphino)ferrocene)] potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 生成 2,5-diphenyl-3,4-bis[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopenta-2,4-dien-1-one
  参考文献：
  名称：

  Multichromophoric Polyphenylene Dendrimers:  Toward Brilliant Light Emitters with an Increased Number of Fluorophores

  摘要：

  Two routes for the introduction of highly fluorescent peryleneimide chromophores into the scaffolding of polyphenylene dendrimers via iterative Diels-Alder cycloadditions are presented. The key intermediates for the divergent dendrimer buildup were two cyclopentadienone branching units carrying two peryleneimides and two masked terminal alkynes. The difference between the two reagents is the mode of incorporation of the chromophores. In the first case, the chromophores were attached to the alpha-position of the tetraphenylcyclopentadienones. In the second case, peryleneimides are used as a "spacer" in the beta-position of the cyclopentadienones giving rise to dendrimers with extended molecular diameters (up to 12 nm) and 24 chromophores within their scaffold. Absorption and emission characteristics of the new multichromophoric nanoparticles were investigated and compared to those of the parent dyes. Additionally, an asymmetrically substituted first-generation dendrimer with six perylene diimide chromophores and one ester functionality is reported. The ester serves as a potential anchor group, and this nanoemitter paves the way to a multichromophoric fluorescence label. All dendrimers have good solubility in common organic solvents, high fluorescence quantum yields, and defined distances between the chromophores, making them attractive candidates for single-molecule spectroscopy.

  DOI：

  10.1021/ja067174m

文献信息

• Multiple Functionalization of Benzophenones Inside Polyphenylene Dendrimers − Toward Entrapped Ions and Radicals
  作者：Stefan Bernhardt、Martin Baumgarten、Manfred Wagner、Klaus Müllen

  DOI：10.1021/ja052856f

  日期：2005.9.1

  Polyphenylene dendrimers possessing a defined number of keto groups in the dendritic scaffold have been synthesized by using a benzophenone-functionalized tetraphenylcyclopentadienone branching unit. A postsynthetic functionalization of the polyphenylene backbone was achieved by reacting the entrapped keto groups with organolithium reagents yielding monodisperse alcohol products. To investigate the accessibility and reactivity of the embedded groups, many functions of different size and nature, for example, the chromophore pyrene, were introduced. Moreover, suitable precursors for the synthesis of dendrimer entrapped species, trityl cations, trityl radicals, and ketyl radical anions, were obtained. To gain insight into the structure of these newly functionalized dendrimers, UV/vis, EPR, and NMR measurements have been performed. They showed a delocalization of the charge/spin into the polyphenylene dendritic arms leading to a stabilization of the ions/radicals. Remarkably, for the ketyl radicals, EPR measurements indicated the occurrence of intermolecular metal-bridged biradicals. They suggest the existence of a dendritic radical network of the dendrimers themselves.
• 3D-Hybrid Networks with Controllable Electrical Conductivity from the Electrochemical Deposition of Terthiophene-Functionalized Polyphenylene Dendrimers
  作者：Hermann John、Roland Bauer、Pamela Espindola、Prashant Sonar、Jürgen Heinze、Klaus Müllen

  DOI：10.1002/anie.200462378

  日期：2005.4.15
• Pushing the Synthetic Limit: Polyphenylene Dendrimers with “Exploded” Branching Units—22-nm-Diameter, Monodisperse, Stiff Macromolecules
  作者：Ekaterina V. Andreitchenko、Christopher G. Clark、Roland E. Bauer、Günter Lieser、Klaus Müllen

  DOI：10.1002/anie.200501368

  日期：2005.10.7
• Soluble Nanographene C₂₂₂: Synthesis and Applications for Synergistic Photodynamic/Photothermal Therapy
  作者：Xiao-Hui Ma、Xing Gao、Jia-Ying Chen、Maofeng Cao、Qixuan Dai、Zhe-Kun Jia、Yuan-Biao Zhou、Xin-Jing Zhao、Chengchao Chu、Gang Liu、Yuan-Zhi Tan

  DOI：10.1021/jacs.3c08822

  日期：2024.1.31
• Multichromophoric Polyphenylene Dendrimers:  Toward Brilliant Light Emitters with an Increased Number of Fluorophores
  作者：Ingo Oesterling、Klaus Müllen

  DOI：10.1021/ja067174m

  日期：2007.4.1

  Two routes for the introduction of highly fluorescent peryleneimide chromophores into the scaffolding of polyphenylene dendrimers via iterative Diels-Alder cycloadditions are presented. The key intermediates for the divergent dendrimer buildup were two cyclopentadienone branching units carrying two peryleneimides and two masked terminal alkynes. The difference between the two reagents is the mode of incorporation of the chromophores. In the first case, the chromophores were attached to the alpha-position of the tetraphenylcyclopentadienones. In the second case, peryleneimides are used as a "spacer" in the beta-position of the cyclopentadienones giving rise to dendrimers with extended molecular diameters (up to 12 nm) and 24 chromophores within their scaffold. Absorption and emission characteristics of the new multichromophoric nanoparticles were investigated and compared to those of the parent dyes. Additionally, an asymmetrically substituted first-generation dendrimer with six perylene diimide chromophores and one ester functionality is reported. The ester serves as a potential anchor group, and this nanoemitter paves the way to a multichromophoric fluorescence label. All dendrimers have good solubility in common organic solvents, high fluorescence quantum yields, and defined distances between the chromophores, making them attractive candidates for single-molecule spectroscopy.