7,7'-dibromo-2,2'-bis(9,9-bis-n-hexylfluorene) | 264925-41-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 7,7'-dibromo-2,2'-bis(9,9-bis-n-hexylfluorene)
• 英文别名: 2,7'-bis(9,9-di-n-hexylfluorene)-2',7-dibromide；2-Bromo-7-(7-bromo-9,9-dihexylfluoren-2-yl)-9,9-dihexylfluorene
• CAS: 264925-41-9
• 化学式: C₅₀H₆₄Br₂
• 分子量: 824.866
• InChiKey: PLRSSALRPLDPMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.8
• 重原子数：
  52
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  7,7'-dibromo-2,2'-bis(9,9-bis-n-hexylfluorene) 在 正丁基锂 、 硼酸三异丙酯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以56%的产率得到2,7'-bis(9,9-di-n-hexylfluorene)-2',7-diboronic acid
  参考文献：
  名称：

  Synthesis and characterization of nitrogen-linked carbazole-containing fluorescent polymers

  摘要：

  AbstractWe have prepared four light‐emitting polymers bearing a chromophore composed of carbazole and fluorene by the Suzuki coupling polycondensation. Two nonconjugated polymers (P3CzBFXy and P2CzFXy) had a chromophore tethered by the p‐xylylene spacer, whose connection point between carbazole and fluorene in addition to the number of fluorene unit was systematically changed to investigate the emission wavelength and intensity. The red‐shifted absorption and emission maximum wavelengths together with the improved fluorescence quantum yield of polymers P3CzBFXy and P2CzFXy indicate that the increment of the number of para‐connected benzene rings included in the chromophore effectively extends the conjugation length. The fact that polymer P3CzBFXy has longer wavelength absorption and emission spectra also indicates the interaction of the carbazole nitrogen lone pair with the oligophenylene moiety. Other two polymers P3CzFPy and P3CzFPym having the heterocycle directly bound to the carbazole nitrogen were prepared to know the character of the carbazole nitrogen lone pair and their influence on the fluorescence behavior. The fluorescence spectra of polymer P3CzFPym bearing the pyrimidine ring gradually red‐shifted in conjunction with the decrease of fluorescence quantum yield on going from toluene solution to CHCl3 solution because of the intramolecular charge transfer at the excited state. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 3729–3735, 2010

  DOI：

  10.1002/pola.24155
• 作为产物：
  描述：

  9,9-二己基-2-溴芴 在 1,1'-双(二苯基膦)二茂铁 、 四(三苯基膦)钯 、 水 、 氢溴酸 、 potassium acetate 、 potassium carbonate 、 sodium hydrogensulfite 、 palladium dichloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 45.0h， 生成 7,7'-dibromo-2,2'-bis(9,9-bis-n-hexylfluorene)
  参考文献：
  名称：

  Delocalization of Positive and Negative Charge Carriers on Oligo- and Poly-fluorenes Studied by Low-Temperature Matrix Isolation Technique

  摘要：

  通过逐步的铃木偶联反应合成了具有明确链长（n = 1–5）的寡氟烯，作为聚氟烯中共轭段的基础。寡氟烯的阳离子和阴离子自由基（n > 2）表现出明显的三条红外吸收，归因于氟烯结构单元之间的SOMO态与骨架中的价态（HOMO）或导电态（LUMO）之间的跃迁。红外带的跃迁能量在单位数范围内从1.2 eV线性下降到0.55 eV，而一维激子跃迁能量在n > 5时显示出明显的饱和。这意味着沿氟烯链的多余电子或空穴的去局部化程度在比中性激子更大的单位数时会达到饱和。

  DOI：

  10.1246/cl.2004.1290

文献信息

• Delocalization of Positive and Negative Charge Carriers on Oligo- and Poly-fluorenes Studied by Low-Temperature Matrix Isolation Technique
  作者：Yoshiko Koizumi、Shu Seki、Anjali Acharya、Akinori Saeki、Seiichi Tagawa

  DOI：10.1246/cl.2004.1290

  日期：2004.10

  Oligofluorenes with well-defined chain length (n = 1–5) have been synthesized by step-by-step Suzuki coupling reaction as the basis sets of conjugated segments in polyfluorenes. Cation and anion radicals of oligofluorenes (n > 2) showed intense and clear three infrared absorptions attributed to transitions between SOMO state delocalized over fluorene moieties and valence (HOMOs) or conduction states (LUMOs) in the backbone. The transition energies of the IR band decreased linearly from 1.2 to 0.55 eV in the range of unit number while 1-D exciton transition energies showed apparent saturation at n > 5. This implied that delocalization degree of excess electrons or holes along fluorene chains would saturate at larger number of units than that of neutral excitons.

  通过逐步的铃木偶联反应合成了具有明确链长（n = 1–5）的寡氟烯，作为聚氟烯中共轭段的基础。寡氟烯的阳离子和阴离子自由基（n > 2）表现出明显的三条红外吸收，归因于氟烯结构单元之间的SOMO态与骨架中的价态（HOMO）或导电态（LUMO）之间的跃迁。红外带的跃迁能量在单位数范围内从1.2 eV线性下降到0.55 eV，而一维激子跃迁能量在n > 5时显示出明显的饱和。这意味着沿氟烯链的多余电子或空穴的去局部化程度在比中性激子更大的单位数时会达到饱和。
• Aryl-aryl dendrimers
  申请人：——

  公开号：US20040169463A1

  公开（公告）日：2004-09-02

  Light emitting devices are described which incorporate, as the light emitting element, a dendrimer of which the constituent dendrons include a conjugated dendritic structure comprising aryl and/or heteroaryl groups connected to each other via bonds between Sp 2 hybridised ring atoms of said aryl or heteroaryl groups.

  描述了一种包含树状分子的发光装置，其中该发光元件的组成部分包括一个共轭树状结构的树状分子，该结构包括通过其芳基和/或杂环芳基之间的Sp2杂化环原子之间的键连接在一起的。
• ARYL-ARYL DENDRIMERS
  申请人：Burn Paul Leslie

  公开号：US20110272688A1

  公开（公告）日：2011-11-10

  Light emitting devices are described which incorporate, as the light emitting element, a dendrimer of which the constituent dendrons include a conjugated dendritic structure comprising aryl and/or heteroaryl groups connected to each other via bonds between sp 2 hybridised ring atoms of said aryl or heteroaryl groups.

  所描述的发光器件包含一个树枝状分子作为发光元件，该树枝状分子的组成部分包括一个共轭的树枝状结构，其中包括芳基和/或杂环芳基基团，这些基团通过其芳基或杂环芳基基团的sp2杂化环原子之间的键连接在一起。
• Aryl-Aryl Dendrimers
  申请人：Burn Paul Leslie

  公开号：US20100127251A1

  公开（公告）日：2010-05-27

  Light emitting devices are described which incorporate, as the light emitting element, a dendrimer of which the constituent dendrons include a conjugated dendritic structure comprising aryl and/or heteroaryl groups connected to each other via bonds between sp 2 hybridized ring atoms of said aryl or heteroaryl groups.

  描述了一种包含树状分子的发光装置，其中树状分子作为发光元件，其组成的树枝包括一个共轭的树状结构，其中包括连接在一起的芳基和/或杂环基团，这些基团之间通过芳基或杂环基团的sp2杂化环原子之间的键连接。
• Synthesis and characterization of N-carbazole end-capped oligofluorene-thiophenes
  作者：Vinich Promarak、Auradee Punkvuang、Taweesak Sudyoadsuk、Siriporn Jungsuttiwong、Sayant Saengsuwan、Tinnagon Keawin、Karnokkorn Sirithip

  DOI：10.1016/j.tet.2007.06.017

  日期：2007.9

  A series of novel N-carbazole end-capped oligofluorene-thiophenes with one, two, three, and four thiophene rings were synthesized using either palladium catalyzed cross-coupling reaction or nickel-catalyzed reductive dimerization. All the oligomers have been characterized by H-1, C-13 NMR, FTIR, UV-vis, PL spectroscopy and mass spectrometry. It has been demonstrated that the optical, thermal, and electrochemical properties of these materials can be tuned by varying the conjugation length of the oligothiophene segment. The terminal carbazole and fluorene moieties of the resulting materials are beneficial for their morphology, conjugation length, and solubility. These bright fluorescent, thermally and electrochemically stable compounds have potential applications as light-emitting and hole-transporting layers in organic light-emitting devices. (c) 2007 Elsevier Ltd. All rights reserved.