1,4-bis[(2-bromophenyl)ethynyl]-2,5-dibromobenzene | 625389-87-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,4-bis[(2-bromophenyl)ethynyl]-2,5-dibromobenzene
• 英文别名: 1,4-dibromo-2,5-bis(2-bromophenylethynyl)benzene；Benzene, 1,4-dibromo-2,5-bis[(2-bromophenyl)ethynyl]-；1,4-dibromo-2,5-bis[2-(2-bromophenyl)ethynyl]benzene
• CAS: 625389-87-9
• 化学式: C₂₂H₁₀Br₄
• 分子量: 593.937
• InChiKey: ZZARREWRZAPGHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1,4-bis[(2-bromophenyl)ethynyl]-2,5-dibromobenzene 在 叔丁基锂 、 氯化铵 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 26.5h， 生成 1,4-bis{[2-(ethoxydimethylsilyl)phenyl]ethynyl}-2,5-bis(ethoxydimethylsilyl)benzene
  参考文献：
  名称：

  Bis-Silicon-Bridged Stilbene Homologues Synthesized by New Intramolecular Reductive Double Cyclization

  摘要：

  A homologous series of bis-silicon-bridged stilbenes has been synthesized on the basis of a new intramolecular reductive cyclization of bis(o-silyl)-diphenylacetylene. Thus, the reaction of bis(o-silyl)-diphenylacetylenes with excess lithium naphthalenide undergoes the two-electron reduction at the acetylene moiety to produce a dianion intermediate, which further undergoes a double cyclization in a 5-exo mode to produce the bis-silicon-bridged stilbenes. This methodology can also be applied to the synthesis of tetrakis-silicon-bridged bis(styryl)benzenes. The silicon-bridged pi-conjugated systems thus prepared show intense fluorescence in the visible region. Comparison of a bis-silicon-bridged stilbene with its carbon analogue demonstrates the substantial effects of the silicon-bridges on the electronic structures and thus on the fluorescence properties.

  DOI：

  10.1021/ja038487+
• 作为产物：
  描述：

  2-溴苯乙炔 、 1,4-二溴-2,5-二碘苯 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以84%的产率得到1,4-bis[(2-bromophenyl)ethynyl]-2,5-dibromobenzene
  参考文献：
  名称：

  EP1548019

  摘要：

  公开号：

文献信息

• -CONJUGATED ORGANIC MATERIAL OF POLYCYCLIC FUSED RING TYPE, INTERMEDIATE THEREFOR, AND PROCESS FOR PRODUCING-CONJUGATED ORGANIC MATERIAL OF POLYCYCLIC FUSED RING TYPE
  申请人：Japan Science and Technology Agency

  公开号：EP1548019A1

  公开（公告）日：2005-06-29

  The invention provides condensed polycyclic π-conjugated organic materials and manufacturing methods for the materials. A metal reducing agent is reacted with a straight-chain, triple bond-containing hydrocarbon (aryl acetylene compound, phenyl acetylene compound), the hydrocarbon being a benzene ring with an organic silicon as a substituent, so as to allow an intramolecular reductive cyclization reaction to proceed between the silicon and the triple-bond carbon. The reaction produces condensed polycyclic π-conjugated organic materials of the invention. The invention provides light-emitting materials applicable for organic electroluminescent devices, condensed polycyclic π-conjugated organic materials applicable for charge transport materials, their intermediate products, and a manufacture method for condensed polycyclic π-conjugated organic materials.

  本发明提供了缩合多环π-共轭有机材料及其制造方法。金属还原剂与直链、含三键的碳氢化合物（芳基乙炔化合物、苯基乙炔化合物）反应，该碳氢化合物是以有机硅为取代基的苯环，从而使硅与三键碳之间发生分子内还原环化反应。反应生成本发明的缩合多环π-共轭有机材料。本发明提供了适用于有机电致发光器件的发光材料、适用于电荷传输材料的缩合多环π共轭有机材料、其中间产物以及缩合多环π共轭有机材料的制造方法。
• n-conjugated organic material of polycyclic fused ring type,intermediate therefor, and process for producing n-conjugated organic material of polycyclic fused ring type
  申请人：Yamaguchi Shigehiro

  公开号：US20060100433A1

  公开（公告）日：2006-05-11

  The invention provides condensed polycyclic π-conjugated organic materials and manufacturing methods for the materials. A metal reducing agent is reacted with a straight-chain, triple bond-containing hydrocarbon (aryl acetylene compound, phenyl acetylene compound), the hydrocarbon being a benzene ring with an organic silicon as a substituent, so as to allow an intramolecular reductive cyclization reaction to proceed between the silicon and the triple-bond carbon. The reaction produces condensed polycyclic π-conjugated organic materials of the invention. The invention provides light-emitting materials applicable for organic electroluminescent devices, condensed polycyclic π-conjugated organic materials applicable for charge transport materials, their intermediate products, and a manufacture method for condensed polycyclic π-conjugated organic materials.

  本发明提供了缩合多环π-共轭有机材料及其制造方法。金属还原剂与直链、含三键的碳氢化合物（芳基乙炔化合物、苯基乙炔化合物）反应，该碳氢化合物是以有机硅为取代基的苯环，从而使硅与三键碳之间发生分子内还原环化反应。反应生成本发明的缩合多环π-共轭有机材料。本发明提供了适用于有机电致发光器件的发光材料、适用于电荷传输材料的缩合多环π共轭有机材料、其中间产物以及缩合多环π共轭有机材料的制造方法。
• <i>o</i>-Carborane-based Biphenyl and<i>p</i>-Terphenyl Derivatives
  作者：Yasuhiro Morisaki、Masato Tominaga、Takuya Ochiai、Yoshiki Chujo

  DOI：10.1002/asia.201400067

  日期：2014.5

  AbstractThe synthesis and properties of biphenyl‐ and p‐terphenyl‐fused o‐carboranes are described. Aryl rings in the biphenyl and p‐terphenyl skeletons are highly coplanar because of the presence of the o‐carborane unit. o‐Carborane exhibits an electron‐withdrawing character via the inductive effect, resulting in a decrease in both the HOMO and LUMO levels of oligophenyls without causing electronic perturbation.
• Synthesis and spectroscopic study of silacyclyne-substituted phenyleneethynylenes
  作者：Guoliang Mao、Akihiro Orita、Daisuke Matsuo、Takayoshi Hirate、Tetsuo Iwanaga、Shinji Toyota、Junzo Otera

  DOI：10.1016/j.tetlet.2009.03.163

  日期：2009.6

  A series of 1,1-dimethyl-4,5:8,9-dibenzo-1-silacycloundeca-4,8-diene-2,6,10-triyne (DST)-substituted phenyleneethynylenes were successfully synthesized by reaction of Me2SiCl2 with dimagnesium dianions which had been prepared from 2,2'-diethynyl(diphenylethyne) derivatives by treatment with 2 equiv of MeMgBr. All the products were white-to-pale yellow powder stable enough to handle in the air, and their photoluminescence spectra were recorded both in solution and in solid state. (C) 2009 Elsevier Ltd. All rights reserved.
• US7705174B2
  申请人：——

  公开号：US7705174B2

  公开（公告）日：2010-04-27