2,7-bis(bromomethyl)-9,9-diethylfluorene | 859437-47-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2,7-bis(bromomethyl)-9,9-diethylfluorene
• 英文别名: 2,7-bis(bromomethyl)-9,9-diethyl-9H-fluorene；9H-Fluorene, 2,7-bis(bromomethyl)-9,9-diethyl-
• CAS: 859437-47-1
• 化学式: C₁₉H₂₀Br₂
• 分子量: 408.176
• InChiKey: IUEWVQYLPFZWOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  2,7-bis(bromomethyl)-9,9-diethylfluorene 在 甲醇 、 sodium tetrahydroborate 、 溶剂黄146 、 肼 作用下， 以 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 甲苯 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  9,9-二乙基芴衍生的无环和大环化合物的合成（第一部分）

  摘要：

  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。

  DOI：

  10.1002/open.202000268
• 作为产物：
  描述：

  2,7-二溴-9,9-二乙基芴 在 正丁基锂 、 三溴化磷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 2,7-bis(bromomethyl)-9,9-diethylfluorene
  参考文献：
  名称：

  Electroluminescent Properties of Novel Fluorene Derivatives with Aromatic Amine Moieties

  摘要：

  2,7-Bis[(4-diphenylamino)phenylvinylene]-9,9-diethylfluorene(BDPDF, 1) and 2,7-bis[(9-ethyl-3-carbazolylvinylene)-9,9-diethylfluorene(BECDF, 2) have been synthesized and characterized. To evaluate electroluminescent performance, compound 1 and 2 were used as emitting materials and dopant materials, respectively and the basic device structure was ITO/m-MTDATA/a-NPD/1 or 2 or doped DPVBi with 1 or 2/Alq 3 /LiF/Al.The devices using BDPDF(1) and BECDF(2) show EL peak at 470 nm and 486 nm. The device showed a blue light-emission with the CIE chromaticity coordinates of (0.177, 0.268).

  DOI：

  10.1080/15421400500365292

文献信息

• 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。
• Design, synthesis, photophysical, and electrochemical properties of DCM-based conjugated polymers for light-emitting devices
  作者：Mahalingam Vanjinathan、Hong-Cheu Lin、A. Sultan Nasar

  DOI：10.1002/pola.26169

  日期：2012.9.15

  measurements. All the polymers show red‐light emission in the range of 566–656 nm both in solution and in solid state. The quantum efficiency of the polymers was in the range of 56–82%. Among the six polymers synthesized, only polymers containing fluorene units show Tg and polymers based on triphenylamine not exhibit Tg. The band gap of these polymers were found to be reasonably low; hyperbranched copolymer containing

  合成了一系列共轭的超支化聚合物，超支化共聚物和包含2-吡喃-4-亚甲基丙二腈（受体）和三苯胺/芴（供体）单元的线性聚合物，并通过FTIR，1 H NMR，热重分析，差示扫描量热法，凝胶渗透色谱，紫外可见光，光致发光和循环伏安法测量。在溶液和固态下，所有聚合物均显示出566–656 nm范围内的红光发射。聚合物的量子效率在56-82％的范围内。在合成的六种聚合物中，只有含芴单元的聚合物显示出T g，而基于三苯胺的聚合物却没有显示出T g。发现这些聚合物的带隙是相当低的。含芴单元的超支化共聚物的最低带隙为2.18 eV，这是由于吸电子CN基团稳定了LUMO能级。发现聚合物的热和溶解行为良好。器件的所有EL光谱（铟锡氧化物/聚（3,4-亚乙基二氧噻吩）：聚（苯乙烯磺酸盐）/聚合物/ 2,9-二甲基-4,7-二苯基-1,10-菲咯啉/三（8 -羟基喹啉（铝）/ LiF / Al）发出红色光，用P
• Synthesis of N-protected indolaldehydes using modified Hass procedure
  作者：Ramalingam Balamurugan、Arasambattu K. Mohanakrishnan

  DOI：10.1016/j.tet.2007.08.035

  日期：2007.11

  A detailed study on oxidation of N-protected bromomethylindoles into the respective aldehydes was carried out. Using a modified Hass procedure, synthesis of aryl-/hetero-aryl aldehydes in particular indolaldehydes is achieved in reasonable yields. (c) 2007 Elsevier Ltd. All rights reserved.
• 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.