2,5-bis(4-bromophenyl)-3,4-di(4-dodecylphenyl)cyclopenta-2,4-dien-1-one | 327603-95-2

• 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-bis(4-bromophenyl)-3,4-di(4-dodecylphenyl)cyclopenta-2,4-dien-1-one
• 英文别名: 2,5-Bis(4-bromophenyl)-3,4-bis(4-dodecylphenyl)cyclopenta-2,4-dien-1-one；2,5-bis(4-bromophenyl)-3,4-bis(4-dodecylphenyl)cyclopenta-2,4-dien-1-one
• CAS: 327603-95-2
• 化学式: C₅₃H₆₆Br₂O
• 分子量: 878.914
• InChiKey: NOZRRNOBARASGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.2
• 重原子数：
  56
• 可旋转键数：
  26
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  1,2-bis(4'-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-4-biphenylyl)ethyne 、 2,5-bis(4-bromophenyl)-3,4-di(4-dodecylphenyl)cyclopenta-2,4-dien-1-one 以 二苯醚 为溶剂， 反应 20.0h， 以66%的产率得到
  参考文献：
  名称：

  Systematic Studies on Structural Parameters for Nanotubular Assembly of Hexa-peri-hexabenzocoronenes

  摘要：

  Thirteen different hexa-peri-hexabenzocoronenes (HBCs) I-III were newly synthesized, and their self-assembling behaviors were investigated. Taking into account also the reported behaviors of amphiphilic HBCs, some structural parameters of HBC essential for the tubular assembly were revealed. Points to highlight include (1) the importance of two phenyl groups attached to one side of the HBC unit, (2) essential roles of long paraffinic side chains on the other side of the phenyl groups, and (3) no necessity of hydrophilic oligo(ethylene glycol) side chains. The hierarchical nanotubular structure, rendered by virtue of a synchrotron radiation technique, was virtually identical to our previous proposal, where the nanotubes are composed of helically coiled bilayer tapes with a tilting angle of similar to 45 degrees. Each tape consists of pi-stacked HBC units, where the inner and outer HBC layers are connected by interdigitation of paraffinic side chains. The coiled structure is most likely caused by a steric congestion of the phenyl groups attached to the HBC unit, whose tilting direction may determine the handedness of the helically chiral nanotube.

  DOI：

  10.1021/ja801179e
• 作为产物：
  描述：

  4,4'-二溴-反-芪 在 氢氧化钾 、 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 potassium tert-butylate 、 溴 、 碘 、 二甲基亚砜 作用下， 以 乙醚 、 乙醇 、 氯仿 、 叔丁醇 为溶剂， 反应 0.08h， 生成 2,5-bis(4-bromophenyl)-3,4-di(4-dodecylphenyl)cyclopenta-2,4-dien-1-one
  参考文献：
  名称：

  功能化六邻六苯并芘烯的合成与自组装

  摘要：

  先前已通过扫描隧道显微镜 (STM) 和扫描隧道光谱 (STS) 研究了六邻六苯并可罗烯 (HBC) 1b 的六烷基取代衍生物的单层。预计连接到芳香核的不同官能团（给电子或吸电子）将影响堆积模式，也可能影响电流-电压特性。为了提供合适的模型系统，开发了一种新的合成方法来合成功能化的 HBC 衍生物。这是通过适当溴取代的二苯基乙炔和 2,3,4,5-四芳基环戊二烯-2,4-二烯-1-酮的 [4 + 2]-环加成，然后用氯化铁 (III)/硝基甲烷氧化环脱氢来实现的. 使用该策略合成了三种不同的取代模式：2-bromo-5、8,11.14,17-pentadodecylhexa-pecri-hexabenzocoronene (2a), 2,5-dibromo-8,11,14,17-pentadodecylhexa-peri-hexabenzocoronene (2b), 和 2,11-dibromo5

  DOI：

  10.1002/1521-3765(20001201)6:23<4327::aid-chem4327>3.0.co;2-7

文献信息

• Direct synthesis of polyaromatic chains of tribenzopentaphene copolymers through cyclodehydrogenation of their poly-tetraphenylbenzene precursors
  作者：Bassam Alameddine、Rajamohanan Sobhana Anju、Suchetha Shetty、Noorullah Baig、Saleh Al-Mousawi、Fakhreia Al-Sagheer

  DOI：10.1002/pola.28739

  日期：2017.11.1

  tribenzopentaphene (TBP) polycyclic aromatic hydrocarbons. The synthetic strategy consists of initially making highly soluble tetraphenylbenzene copolymers 4a–c, followed by a cyclodehydrogenation/aromatization reaction to obtain target polymers 5a–c. The polymers were characterized by gel permeation chromatography, FT‐IR, UV‐vis, emission, 1H‐, and 13C‐nuclear magnetic resonance spectroscopy. The target polymers

  据报道，三种基于聚芳烃的聚合物包含梯形三苯并五苯（TBP）多环芳烃的共聚单体。合成策略包括首先制备高可溶性四苯基苯共聚物4a–c，然后进行环脱氢/芳构化反应以获得目标聚合物5a–c。通过凝胶渗透色谱，FT-IR，UV-vis，发射，1 H-和13 C-核磁共振波谱对聚合物进行表征。目标聚合物5a–c揭示在430–480 nm范围内的发射光谱；因此，使他们有资格充当蓝色发光体。对聚合物光学性质及其与密度泛函理论计算的相关性的研究表明，TBP核的平面度因在其宽边引入十二烷基而引起的平面度变形。©2017 Wiley Periodicals，Inc. J. Polym。科学，A部分：Polym。化学 2017年，55，3565-3572
• Synthesis of Arylamine Tribenzopentaphenes and Investigation of their Hole Mobility
  作者：Bassam Alameddine、Andrew H. Rice、Christine Luscombe、Titus A. Jenny

  DOI：10.1002/open.201500064

  日期：2015.8

  features, and thus, unexpected low hole mobilities. The synthetic strategy we show herein, however, offers the possibility to decorate the TBP core structure with various charge‐carrier peripheral groups and optimized alkyl chains, which should improve the crystalline property of their thin films upon deposition, leading consequently to a better hole transport mobility.

  我们报告了两个三苯并[ fj，ij，rst的通用合成带有两个连接在芳族核相反两端的二芳基胺取代基的]五苯酚（TBP）衍生物。双二芳基胺-TBP化合物的场效应晶体管（FET）器件是使用旋涂在不同浓度，旋转速度和溶剂条件下制造的。发射光谱和通过原子力显微镜（AFM）进行的表面研究表明，由于芳族核强烈π-π堆积而形成的聚集体形成了岛状特征，因此产生了意想不到的低空穴迁移率。然而，我们在本文中展示的合成策略提供了用各种电荷载流子外围基团和优化的烷基链修饰TBP核心结构的可能性，这将改善沉积时其薄膜的结晶性能，从而导致更好的空穴传输流动性。