3-(4-bromophenyl)-2,4,5-triphenylcyclopentadienone | 64757-17-1

• 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: 3-(4-bromophenyl)-2,4,5-triphenylcyclopentadienone
• 英文别名: 3-(4-Bromophenyl)-2,4,5-triphenylcyclopenta-2,4-dien-1-one
• CAS: 64757-17-1
• 化学式: C₂₉H₁₉BrO
• 分子量: 463.373
• InChiKey: CPSWCGIPNVTISB-UHFFFAOYSA-N

物化性质

• 沸点：
  653.1±55.0 °C(Predicted)
• 密度：
  1.376±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(4-bromophenyl)-2,4,5-triphenylcyclopentadienone 在 盐酸 、 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 96.17h， 生成 3-(4-Amino-phenyl)-2,4,5-triphenyl-cyclopenta-2,4-dienone
  参考文献：
  名称：

  肽官能化的聚亚苯基树枝状聚合物

  摘要：

  该贡献描述了聚苯撑树状聚合物的合成，所述聚苯撑树状聚合物被多达16个赖氨酸残基官能化或被由5个赖氨酸或谷氨酸重复序列和C-或N-末端半胱氨酸残基组成的短肽序列取代。通过一系列Diels-Alder环加成反应和环戊二烯酮结构单元的脱保护反应来制备聚苯树枝状聚合物。通过在最后的Diels-Alder加成反应中使用氨基酸取代的环戊二烯酮，可以将单个氨基酸引入树枝状聚合物的外围。或者，通过化学选择反应连接肽序列，该化学选择反应涉及将寡肽的半胱氨酸残基的巯基加至存在于树状聚合物表面上的马来酰亚胺部分。

  DOI：

  10.1016/s0040-4020(03)00461-7

文献信息

• Borazino-Doped Polyphenylenes
  作者：Davide Marinelli、Francesco Fasano、Btissam Najjari、Nicola Demitri、Davide Bonifazi

  DOI：10.1021/jacs.7b01477

  日期：2017.4.19

  hybrid polyphenylenes featuring controlled orientations and dosages of the doping B3N3 rings have been prepared. Detailed photophysical investigations showed that as the doping dosage is increased, the strong luminescent signal is progressively reduced. This suggests that the presence of the B3N3 rings engages additional deactivation pathways, possibly involving excited states with an increasing charge-separated

  首次报道了利用乙炔基和乙炔基之间的脱羰[4 + 2] Diels-Alder环加成反应合成两个系列的硼氮杂掺杂聚苯，其中一个或多个芳基单元被硼嗪环取代。四苯基环戊二烯酮衍生物。由于硼嗪核的 N 和 B 原子上的芳基取代基上的不同基团可以对硼嗪核进行功能化，因此我们制备了具有不同掺杂剂量和取向的硼嗪掺杂聚亚苯基。为此，制备了两个分子模块：核心和支化单元。根据中心芳族模块和反应基团的化学性质，模块的每个共价组合产生一种独特的掺杂模式。通过这种方法，已经制备了具有可控取向和剂量的掺杂 B3N3 环的三和六支化杂化聚苯。详细的光物理研究表明，随着掺杂剂量的增加，强发光信号逐渐减弱。这表明 环的存在参与了额外的失活途径，可能涉及具有增加的电荷分离特性的激发态，这在全碳类似物中受到限制。值得注意的是，对于那些具有低掺杂剂量的杂化聚苯结构，观察到取向掺杂对荧光量子产率的强烈影响。最后，我们表明
• Synthesis and Characterization of Dendritic Multichromophores Based on Rylene Dyes for Vectorial Transduction of Excitation Energy
  作者：Tanja Weil、Erik Reuther、Cornelia Beer、Klaus Müllen

  DOI：10.1002/chem.200305359

  日期：2004.3.19

  The synthesis of dendritic multichromophores based on a rigid polyphenylene scaffold is presented. Different rylene chromophores are incorporated into the core, the branches, and the surface of the dendrimer. In this way, two generations of dendritic dyads consisting of a terrylenediimide core, a stiff polyphenylene scaffold, and a perylenemonoimide periphery were obtained. Furthermore, the first synthetic

  提出了基于刚性聚苯撑支架的树枝状多发色团的合成。不同的萘嵌苯生色团被并入树枝状聚合物的核心，分支和表面。以这种方式，获得了由三甲苯二酰亚胺核，坚硬的聚亚苯基支架和a单酰亚胺周边构成的两代树状二元体。此外，引入了第一种合成方法用于树突状三联体。该大分子的外球由萘单酰亚胺发色团形成，而per单酰亚胺基团位于树枝状支架中，并且r二酰亚胺发色团充当核心分子。该多色团在可见光谱的整个范围内吸收，并显示出分离良好的吸收包络线。
• The Absorption Spectra of Tetracyclones. IV^1,2
  作者：Stephen B. Coan、Donald E. Trucker、Ernest I. Beckerr

  DOI：10.1021/ja01606a018

  日期：1955.1
• Polyphenylene Dendrimers with Different Fluorescent Chromophores Asymmetrically Distributed at the Periphery
  作者：Tanja Weil、Uwe M. Wiesler、Andreas Herrmann、Roland Bauer、Johan Hofkens、Frans C. De Schryver、Klaus Müllen

  DOI：10.1021/ja010579g

  日期：2001.8.1

  A new synthetic approach leading to asymmetrically substituted polyphenylene dendrimers is presented. Following this method, polyphenylene dendrimers decorated with an increasing number of chromophores at the periphery have been obtained up to the second generation. Especially the synthesis of a polyphenylene dendrimer beating three donor chromophores and one acceptor chromophore has been realized. Intramolecular energy transfer within this molecule is demonstrated by applying absorption and fluorescence measurements.
• Toward Nanoamphiphiles:  Efficient Synthesis of Desymmetrized Polyphenylene Dendrimers
  作者：G. Mihov、I. Scheppelmann、K. Müllen

  DOI：10.1021/jo048998u

  日期：2004.11.1

  A new synthetic approach for the desymmetrization of polyphenylene dendrimers (PPDs) is described. Tetrakis(4-ethynylphenyl)methane undergoes facile Diels-Alder cycloaddition with substoichiometric quantities of tetraphenylcyclopentadienones bearing one polar functional group. A single ethynyl group is thereby converted to a rigid, selectively functionalized polyphenylene moiety, which serves as a focal point for further transformations or interfacial anchoring. This is the key feature for the design of desymmetrized monodisperse macromolecules with a spherical shape. The remaining unreacted ethynyl groups provide a trifold core for the stepwise elaboration of first- and second-generation polyphenylene dendrons, which may, in turn, bear specific numbers of different peripheral functional groups at their terminae. Moreover, the resulting macromolecules exhibit the characteristic shape-persistence and monodispersity of PPDs. This approach is an important achievement in nanosciences, especially for tailoring new nanoamphiphiles. It is also of synthetic importance, as it enables the separation of two regioisomeric polyphenylene dendrimers for the first time.