2,4,7-tris(bromomethyl)-9,9-diethylfluorene | 859437-48-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2,4,7-tris(bromomethyl)-9,9-diethylfluorene
• 英文别名: 2,4,7-tris(bromomethyl)-9,9-diethyl-9H-fluorene
• CAS: 859437-48-2
• 化学式: C₂₀H₂₁Br₃
• 分子量: 501.099
• InChiKey: MWCJKYSOVFLEQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,4,7-tris(bromomethyl)-9,9-diethylfluorene 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以91%的产率得到2,4,7-tris(iodomethyl)-9,9-diethylfluorene
  参考文献：
  名称：

  带有卤代甲基的芴衍生物：晶体状态下的合成，分子结构和卤素/氢键模式

  摘要：

  介绍了在芳香族骨架的2、4和7位上带有卤代甲基的9,9-二乙基芴的合成，以及通过X射线衍射进行的分析。此外，还描述了有效的一步合成9,9-二乙基芴-2,4,7-三甲醛，提供比已知的三步反应顺序高三倍的甲醛产率。氯甲基和溴甲基取代的芴的晶体堆积主要通过Hal· ·· Hal和C–H ··· Hal接触来稳定，而碘取代的类似物的堆积则受三角形I 3合子C–H ·的影响。 ·· π和C-H ···我的相互作用。

  DOI：

  10.1002/ejoc.201801621
• 作为产物：
  描述：

  芴 在 氢溴酸 、 溶剂黄146 、 potassium iodide 、 potassium hydroxide 作用下， 以 氯仿 、 二甲基亚砜 为溶剂， 反应 96.0h， 生成 2,4,7-tris(bromomethyl)-9,9-diethylfluorene
  参考文献：
  名称：

  带有2至7个邻苯二甲酰亚胺甲基的芴衍生物：合成，晶体结构和向胺的转化

  摘要：

  这项工作的主题是，合成最多包含七个邻苯二甲酰亚胺甲基的芴衍生物，通过X射线衍射分析以及将其转化为胺。晶体结构的特征是存在CH- H⋅⋅⋅O，CH- H⋅⋅⋅π和π⋅⋅⋅π相互作用以及C = O⋅⋅⋅π接触。在氯仿和二氯甲烷的情况下，Cl⋅⋅⋅O = C，Cl⋅⋅⋅Cl，Cl⋅⋅⋅π和CH- H⋅⋅⋅Cl相互作用会影响晶体堆积。图集 （10）的十元超分子基序，由C- H⋅⋅⋅创建在某些晶体结构中可以识别出O键。

  DOI：

  10.1002/ejoc.202100125

文献信息

• Syntheses of Acyclic and Macrocyclic Compounds Derived from 9,9‐Diethylfluorene (Part I)
  作者：Pierre Seidel、Monika Mazik

  DOI：10.1002/open.202000268

  日期：2020.11

  In addition to the seventeen 2,4,7‐trisubstituted 9,9‐diethylfluorenes, two macrocyclic compounds were prepared on the basis of 2,7‐bis(aminomethyl)‐9,9‐diethylfluorene. The excellent yield of the macrocyclization reaction is worth a special mention. Both the acyclic and the macrocyclic fluorene‐based compounds have, among other things, the potential to act as artificial receptors for different substrates

  在2,4的基础上制备了一系列由三个侧臂组成的新9,9-二乙基芴，每个侧臂带有杂环、双(羧甲基)氨基、双(氨基甲酰甲基)氨基、双(乙氧基羰基甲基)氨基或氨基。 ,7-三(溴甲基)-9,9-二乙基芴。咪唑基、苯并咪唑基、吡唑基、吡咯基、1,3-二氧异吲哚基和吡啶鎓基团被视为杂环单元，通过-CH 2 -、-CH 2 NHCH 2 -或-CH 2 N=CH-连接基连接到芳香族骨架上。除了十七种2,4,7-三取代的9,9-二乙基芴之外，还制备了两种基于2,7-双(氨基甲基)-9,9-二乙基芴的大环化合物。大环化反应的优异收率值得特别提及。除其他外，无环和大环芴基化合物都具有充当不同底物的人工受体的潜力，类似于由苯或联苯核心组成的已知受体。
• Synthesis, optical properties, and blue electroluminescence of fluorene derivatives containing multiple imidazoles bearing polyaromatic hydrocarbons
  作者：Dhirendra Kumar、K.R. Justin Thomas、Yu-Lin Chen、Yung-Cheng Jou、Jwo-Huei Jou

  DOI：10.1016/j.tet.2013.01.046

  日期：2013.3

  Fluorene decorated with multiple imidazole units in a non-conjugated fashion and featuring polyaromatic hydrocarbons such as anthracene or pyrene were synthesized and characterized as blue emitters suitable for application in organic light-emitting diodes. The optical absorption and emission peak profiles remained unaltered on increasing the imidazole loading on fluorene. But the molar extinction coefficient progressively increased on introduction of additional imidazole unit attributable to the increment in the chromophore density. Replacement of phenyl group at the C-2 of imidazole nucleus with polyaromatic hydrocarbons such as anthracene and pyrene led to a red-shift in the absorption and emission spectra due to their characteristic absorption features. All the compounds exhibited high thermal decomposition temperature in the range 395-509 degrees C showing significant thermal robustness. The anthracene and pyrene derivatives were demonstrated as efficient blue emitters in 4,4'-di(9H-carbazol-9-y1)-1,1'-biphenyl host for multilayered organic light-emitting diodes. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of Two-Photon Absorbing Unsymmetrical Branched Chromophores through Direct Tris(bromomethylation) of Fluorene
  作者：Sheng Yao、Kevin D. Belfield

  DOI：10.1021/jo0503512

  日期：2005.6.1

  Branched fluorene-based chromophores bearing electron-donating diphenylamino or electron-withdrawing nitro groups were synthesized as well as their linear analogues. An efficient synthetic method was developed via a novel 2,4,7-tris(bromomethyl)-9,9-diethylfluorene intermediate. The bromomethyl groups in this key intermediate were converted to either phosphonate or carboxaldehyde moieties, facilitating preparation of a high functionality branched structure. It was found that the reactivity at position 4 is attenuated in the bromomethyl and phosphorylated derivates, facilitating the selective and systematic functionalization of the fluorenyl system. All compounds were stable up to ca. 350 degrees C, except for a sterically crowded branched derivative. The linear optical properties of the compounds were investigated by UV-visible, steady-state fluorescence, and excitation anisotropy spectroscopic measurements. Fluorescence quantum yields were greater than or equal to 0.84 for symmetric linear and unsymmetric branched derivatives. Very high two-photon absorption (2PA) cross-sections were achieved (5765 GM at 520 nm and 4194 GM at 570 nm), as determined with use of picosecond and femtosecond laser excitation sources, respectively.
• Fluorene Derivatives Bearing Two to Seven Phthalimidomethyl Groups: Syntheses, Crystal Structures and Conversion to Amines
  作者：Pierre Seidel、Wilhelm Seichter、Anke Schwarzer、Monika Mazik

  DOI：10.1002/ejoc.202100125

  日期：2021.5.26

  The syntheses of fluorene derivatives containing up to seven phthalimidomethyl groups, their analyses by X-ray diffraction as well as their conversion to amines are the topics of this work. The crystal structures are characterized by the presence of C−H⋅⋅⋅O, C−H⋅⋅⋅π and π⋅⋅⋅π interactions as well as C=O⋅⋅⋅π contacts. In the case of the chloroform and dichloromethane solvates the Cl⋅⋅⋅O=C, Cl⋅⋅⋅Cl,

  这项工作的主题是，合成最多包含七个邻苯二甲酰亚胺甲基的芴衍生物，通过X射线衍射分析以及将其转化为胺。晶体结构的特征是存在CH- H⋅⋅⋅O，CH- H⋅⋅⋅π和π⋅⋅⋅π相互作用以及C = O⋅⋅⋅π接触。在氯仿和二氯甲烷的情况下，Cl⋅⋅⋅O = C，Cl⋅⋅⋅Cl，Cl⋅⋅⋅π和CH- H⋅⋅⋅Cl相互作用会影响晶体堆积。图集 （10）的十元超分子基序，由C- H⋅⋅⋅创建在某些晶体结构中可以识别出O键。
• Fluorene Derivatives Bearing Halogenomethyl Groups: Synthesis, Molecular Structures, and Halogen/Hydrogen Bonding Patterns in the Crystalline State
  作者：Pierre Seidel、Anke Schwarzer、Monika Mazik

  DOI：10.1002/ejoc.201801621

  日期：2019.2.21

  The syntheses of 9,9‐diethylfluorenes bearing halogenomethyl groups in the 2, 4 and 7 positions of the aromatic skeleton, as well as their analyses by X‐ray diffraction are presented. In addition, the efficient one‐step synthesis of 9,9‐diethylfluorene‐2,4,7‐tricarbaldehyde, providing threefold higher yield of the carbaldehyde than the known three‐step reaction sequence, is also described. The crystal

  介绍了在芳香族骨架的2、4和7位上带有卤代甲基的9,9-二乙基芴的合成，以及通过X射线衍射进行的分析。此外，还描述了有效的一步合成9,9-二乙基芴-2,4,7-三甲醛，提供比已知的三步反应顺序高三倍的甲醛产率。氯甲基和溴甲基取代的芴的晶体堆积主要通过Hal· ·· Hal和C–H ··· Hal接触来稳定，而碘取代的类似物的堆积则受三角形I 3合子C–H ·的影响。 ·· π和C-H ···我的相互作用。