2-(2-bromo-9,9-dihexyl-9H-fluoren-7-yl)-9,9-dihexyl-7-(9,9-dihexyl-9H-fluoren-2-yl)-9H-fluorene | 483363-24-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-(2-bromo-9,9-dihexyl-9H-fluoren-7-yl)-9,9-dihexyl-7-(9,9-dihexyl-9H-fluoren-2-yl)-9H-fluorene
• 英文别名: 2-bromo-9,9,9',9',9'',9''-hexahexyl-7,2':7',2''-terfluorene
• CAS: 483363-24-2
• 化学式: C₇₅H₉₇Br
• 分子量: 1078.5
• InChiKey: QRMPHDVQCALMLD-UHFFFAOYSA-N

物化性质

• 密度：
  1.047±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  24.41
• 重原子数：
  76.0
• 可旋转键数：
  32.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  2-(2-bromo-9,9-dihexyl-9H-fluoren-7-yl)-9,9-dihexyl-7-(9,9-dihexyl-9H-fluoren-2-yl)-9H-fluorene 在 正丁基锂 、 硼酸三异丙酯 、 盐酸 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 12.75h， 以89.9%的产率得到(9,9,9’,9’,9’’,9’’-hexahexyl-9H,9’H,9’’H,9’’’H-2,2’:7’,2’’-terfluoren-7-yl)boronic acid
  参考文献：
  名称：

  Synthesis and Properties of Monodisperse Oligofluorene-Functionalized Truxenes:  Highly Fluorescent Star-Shaped Architectures

  摘要：

  This paper describes the strategy toward novel monodisperse, well-defined, star-shaped oligofluorenes with a central truxene core and from monofluorene to quaterfluorene arms. Introduction of solubilizing n-hexyl groups at both fluorene and truxene moieties results in highly soluble, intrinsically two-dimensional nanosized macromolecules T1-T4. The radius for the largest oligomer of ca. 3.9 nm represents one of the largest known star-shaped conjugated systems. Cyclic voltammetry experiments reveal reversible or quasi-reversible oxidation and reduction processes (E-ox = +0.74 to 0.80 V, E-red = -2.66 to 2.80 eV vs Fc/Fc(+)), demonstrating excellent electrochemical stability toward both p- and n-doping, while the band gaps of the oligomers are quite high (E-g(CV) = 3.20-3.40 eV). Close band gaps of 3.05-3.29 eV have been estimated from the electron absorption spectra. These star-shaped macromolecules demonstrate good thermal stability (up to 400-420 degreesC) and improved glass transition temperatures with an increase in length of the oligofluorene arms (from T-g = 63 degreesC for T1 to 116 degreesC for T4) and show very efficient blue photoluminescence (lambda(PL) = 398-422 nm) in both solution (Phi(PL) = 70-86%) and solid state (PhiPL = 43-60%). Spectroelectrochernical experiments reveal that compounds T1-T4 are stable electrochromic systems which change their color reversibly from colorless in the neutral state (similar to340-400 nm) to colored (from red to purple color; similar to500-600 nm) in the oxidized state.

  DOI：

  10.1021/ja039228n
• 作为产物：
  描述：

  9,9-二己基-2,7-二溴代芴 在 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 36.75h， 生成 2-(2-bromo-9,9-dihexyl-9H-fluoren-7-yl)-9,9-dihexyl-7-(9,9-dihexyl-9H-fluoren-2-yl)-9H-fluorene
  参考文献：
  名称：

  Synthesis and Properties of Monodisperse Oligofluorene-Functionalized Truxenes:  Highly Fluorescent Star-Shaped Architectures

  摘要：

  This paper describes the strategy toward novel monodisperse, well-defined, star-shaped oligofluorenes with a central truxene core and from monofluorene to quaterfluorene arms. Introduction of solubilizing n-hexyl groups at both fluorene and truxene moieties results in highly soluble, intrinsically two-dimensional nanosized macromolecules T1-T4. The radius for the largest oligomer of ca. 3.9 nm represents one of the largest known star-shaped conjugated systems. Cyclic voltammetry experiments reveal reversible or quasi-reversible oxidation and reduction processes (E-ox = +0.74 to 0.80 V, E-red = -2.66 to 2.80 eV vs Fc/Fc(+)), demonstrating excellent electrochemical stability toward both p- and n-doping, while the band gaps of the oligomers are quite high (E-g(CV) = 3.20-3.40 eV). Close band gaps of 3.05-3.29 eV have been estimated from the electron absorption spectra. These star-shaped macromolecules demonstrate good thermal stability (up to 400-420 degreesC) and improved glass transition temperatures with an increase in length of the oligofluorene arms (from T-g = 63 degreesC for T1 to 116 degreesC for T4) and show very efficient blue photoluminescence (lambda(PL) = 398-422 nm) in both solution (Phi(PL) = 70-86%) and solid state (PhiPL = 43-60%). Spectroelectrochernical experiments reveal that compounds T1-T4 are stable electrochromic systems which change their color reversibly from colorless in the neutral state (similar to340-400 nm) to colored (from red to purple color; similar to500-600 nm) in the oxidized state.

  DOI：

  10.1021/ja039228n

文献信息

• Monodisperse fluorene oligomers exhibiting strong dipolar coupling interactions
  作者：Rémi Anémian、Jean-Christophe Mulatier、Chantal Andraud、Olivier Stéphan、Jean-Claude Vial

  DOI：10.1039/b201414a

  日期：2002.7.11

  Well-defined fluorene oligomers (n = 1 to 6) were prepared step by step using Suzuki and Yamamoto couplings, while absorption and photoluminescence properties evidenced very large dipolar coupling interactions between fluorene moieties.

  通过逐步Suzuki和Yamamoto偶联反应，制备了定义明确的芴寡聚物（n = 1到6），其吸收和光致发光性质表明芴基团之间存在非常大的偶极耦合相互作用。
• 一种9,9-二烷基芴为结构单元的共轭烯类单体及其合成方法
  申请人：青岛科技大学

  公开号：CN113461479A

  公开（公告）日：2021-10-01

  本发明涉及一种9,9‑二烷基芴为结构单元的共轭烯类单体及其合成方法，属于有机合成技术领域。本发明9,9‑二烷基芴为结构单元的共轭烯类单体的结构式为其中R为不同碳原子数目(6‑30)的直链或支链烷基；n为结构单元数(n＝1～6)。本发明通过芴或芴齐聚物的溴代、乙酰化后还原，反复利用Suzuki偶联反应，构筑各中间体的官能团，得到不同共轭长度的以9,9‑二烷基芴为核的功能性烯类单体；可解决芴单元有机小分子的化学反应灵活拓展的问题。
• Microwave-enhanced multiple Suzuki couplings toward highly luminescent starburst monodisperse macromolecules
  作者：Wen-Yong Lai、Qing-Quan Chen、Qi-Yuan He、Qu-Li Fan、Wei Huang

  DOI：10.1039/b517841j

  日期：——

  A facile and powerful microwave-enhanced multiple Suzuki coupling methodology has been developed and a novel series of highly luminescent six-arm monodisperse macromolecules have thus been prepared with high yield and purity.

  一种简便而强大的微波增强多重铃木偶联的方法已经被开发出来，因此制备了一系列新型的高度发光的六臂单分散大分子，具有高产率和高纯度。
• Synthesis and Characterization of Luminescent Rod–Coil Block Copolymers by Atom Transfer Radical Polymerization: Utilization of Novel End-Functionalized Terfluorenes as Macroinitiators
  作者：Panagiotis K. Tsolakis、Joannis K. Kallitsis

  DOI：10.1002/chem.200390115

  日期：2003.2.17

  Two novel, rigid, photoluminescent, substituted terfluorene derivatives were synthesized by utilizing direct bromination and Suzuki coupling reactions. These oligomers were used as initiators for the atom transfer radical polymerization (ATRP) of styrene and tert-butyl acrylate. Thus, diblock and triblock rod-coil block copolymers were prepared with well-defined structure, as far as their size and

  利用直接溴化和Suzuki偶联反应合成了两种新颖的，刚性的，光致发光的，取代的三芴衍生物。这些低聚物用作苯乙烯和丙烯酸叔丁酯的原子转移自由基聚合（ATRP）的引发剂。因此，就其尺寸和形状而言，制备了具有明确结构的二嵌段和三嵌段杆-线圈嵌段共聚物。在大多数情况下，获得的分子量高达约21000，多分散指数不超过1.5。共聚物在溶液中发出蓝光，当从溶液转变为固态时，它们的发光性能实际上保持不变。即使在高温下退火后，在固态下也未观察到基态聚集或准分子形成。
• 2,3,7,8,12,13-Hexaaryltruxenes: An ortho-Substituted Multiarm Design and Microwave-Accelerated Synthesis toward Starburst Macromolecular Materials with Well-Defined π Delocalization
  作者：Wen-Yong Lai、Ruidong Xia、Donal D. C. Bradley、Wei Huang

  DOI：10.1002/chem.201000168

  日期：——

  electronic interaction between the arms, even for the shortest armed oligomer Tr1. A clear linear relationship of both 1/λmax and Eg with the inverse of (n+1) for these branched systems was found. Our findings highlight a novel molecular design comprising an ortho‐substituted, multiarmed architecture that would allow the introduction of isotropic physical and/or mechanical properties, while at the same time

  我们在此介绍一种新颖的设计，并基于新颖的2,3,7,8,12,13-六芳基甲苯骨架向“均质”星爆芴系统进行有效合成。受控的微波加热为这些具有大空间位阻的大体积材料的合成提供了一个简便而有效的方法，这为以高收率和高纯度快速便捷地获得结构明确的复杂有机半导体（OSC）提供了一种途径。热重分析（TGA）和差示扫描量热法（DSC）以及广角X射线衍射（WAXD）研究表明，所得材料具有良好的热稳定性和出色的玻璃状结构。此外，与它们对应的三臂替换T1 – T4相比，引进的邻位周围的truxene芯取代基TR1 - Tr4的最大吸收的结果在显著蓝移（7-24的纳米）λ最大和更高的能量的光学间隙（Ë克）。与相应的线性，棒状低聚芴对应物（OFX）的比较研究表明，TrX（X = 1–4）结构中最长的对共轭链段在确定其电子性质中起主要作用。UV / Vis数据和循环伏安法（CV）研究表明，即使对于最短的武装低聚物