1,5-dibromo-2,4-bis(phenylethynyl)benzene | 546112-73-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,5-dibromo-2,4-bis(phenylethynyl)benzene
• 英文别名: 1,5-Dibromo-2,4-bis(2-phenylethynyl)benzene
• CAS: 546112-73-6
• 化学式: C₂₂H₁₂Br₂
• 分子量: 436.145
• InChiKey: QPZLUQLDHQYRAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  24
• 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：

  1,5-dibromo-2,4-bis(phenylethynyl)benzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三苯胂 、 potassium carbonate 、 N,N-二异丙基乙胺 、 cesium fluoride 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 1,3-bis[(3'-(4"-thioacetyl)phenylethynyl)phenyl]-4,6-bis(phenylethynyl)benzene
  参考文献：
  名称：

  Improved and new syntheses of potential molecular electronics devices

  摘要：

  New syntheses of ethyl and nitro substituted oligo(phenylene ethynylene)s (OPEs) have been developed. To further explore whether the presence of nitro functionality in OPEs leads to switching and memory capabilities, new nitro substituted OPEs have been designed and synthesized. An isatogen-based system, a structure that is isomeric to the nitro OPE, has been synthesized. Additionally, pyridine-based and chromium-based compounds have been synthesized. We surmise that redox reactions of these candidates may impart switching capabilities and electrochemical studies are shown. U-shaped OPEs were synthesized to inhibit leakage of metals deposited during formation of top contacts on self-assembled monolayers (SAMs). The OPEs contain either thiol-based moieties or isonitrile groups to enable formation of SAMs on metal substrates. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00246-1
• 作为产物：
  描述：

  1,3-二溴苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 TEA 、 碘 作用下， 以 四氢呋喃 、 硫酸 为溶剂， 反应 26.0h， 生成 1,5-dibromo-2,4-bis(phenylethynyl)benzene
  参考文献：
  名称：

  Improved and new syntheses of potential molecular electronics devices

  摘要：

  New syntheses of ethyl and nitro substituted oligo(phenylene ethynylene)s (OPEs) have been developed. To further explore whether the presence of nitro functionality in OPEs leads to switching and memory capabilities, new nitro substituted OPEs have been designed and synthesized. An isatogen-based system, a structure that is isomeric to the nitro OPE, has been synthesized. Additionally, pyridine-based and chromium-based compounds have been synthesized. We surmise that redox reactions of these candidates may impart switching capabilities and electrochemical studies are shown. U-shaped OPEs were synthesized to inhibit leakage of metals deposited during formation of top contacts on self-assembled monolayers (SAMs). The OPEs contain either thiol-based moieties or isonitrile groups to enable formation of SAMs on metal substrates. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00246-1

文献信息

• Synthesis and structures of helical polycyclic aromatic hydrocarbons bearing aryl substituents at the most sterically hindered positions
  作者：Yanzhong Zhang、Jeffrey L. Petersen、Kung K. Wang

  DOI：10.1016/j.tet.2007.11.073

  日期：2008.2

  polycyclic aromatic hydrocarbons bearing one or two aryl substituents at the most sterically hindered positions to cause helical twists. The dynamic behaviors involving the helix inversion and the restricted rotation of the aryl substituents were investigated by temperature-dependent NMR studies. The X-ray structure of an indeno-fused 1-phenylpentahelicene derivative showed severe distortion of the [5]helicene

  建立了一个三步合成序列，从苯甲二烯二炔与芳基叔丁基酮之间的缩合反应开始，以使人们容易接近在最受阻位上带有一个或两个芳基取代基的有角稠合多环芳烃，从而引起螺旋扭曲。通过依赖于温度的NMR研究来研究涉及螺旋反转和芳基取代基的受限旋转的动力学行为。茚并稠合的1-苯基戊烯衍生物的X射线结构显示，[5]螺旋系统因平面度而严重变形。
• METHOD FOR PRODUCING AROMATIC COMPOUND
  申请人：Kuwabara Hirokazu

  公开号：US20100137617A1

  公开（公告）日：2010-06-03

  Disclosed is a method for producing an aromatic compound represented by the general formula (2) below, which is characterized in that a compound represented by the general formula (1) below is reacted with a sulfur compound (at least one member selected from the group consisting of sulfur, hydrogen sulfide, metal hydrosulfides and metal sulfides) or a selenium compound. (In the formula (1), R 1 represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an ester group, an optionally substituted alkyl group having 1-18 carbon atoms or the like; R 2 represents a halogen atom; R 3 represents a hydrogen atom, C≡C—R 1 or R 2 ; and n represents an integer of 0-4. When n is not less than 2, R 3 's may be the same as or different from each other.) (In the formula (2), R 1 , R 3 and n are as defined in the formula (1); and X represents a sulfur atom or a selenium atom.)

  公开了一种生产下式（2）所表示的芳香化合物的方法，其特征在于将下式（1）所表示的化合物与硫化物（从硫、氢硫化物、金属氢硫化物和金属硫化物组成的群体中选择至少一种）或硒化物反应。（在式（1）中，R1表示氢原子、卤素原子、羟基、氰基、硝基、酯基、有1-18个碳原子的可选取代烷基或类似物；R2表示卤素原子；R3表示氢原子、C≡C—R1或R2；n表示0-4的整数。当n不小于2时，R3可以相同也可以不同。）（在式（2）中，R1、R3和n如式（1）所定义；X表示硫原子或硒原子。）
• Successive Annulation to Fully Zigzag-Edged Polycyclic Heteroaromatic Hydrocarbons with Strong Blue–Green Electroluminescence
  作者：Peirong Qiang、Zuobang Sun、Minqiang Wan、Xiaofeng Wang、Palani Thiruvengadam、Chiranjeevi Bingi、Weiwei Wei、Wenqing Zhu、Dongqing Wu、Fan Zhang

  DOI：10.1021/acs.orglett.9b01487

  日期：2019.6.21

  A Bronsted-acid-promoted alkyne benzannulation approach was developed to synthesize the amino-substituted dibenze[a,j]anthracence derivatives in excellent yields, which were directly converted to fully zigzag-edged polycyclic heteroaromatic hydrocarbons via a nitrogen-directed electrophilic borylation. As the dopant in a blue-green electroluminescent device, the resulted compound exhibited relatively high stability.
• Organic Field-Effect Transistors Based on 2,6-Diphenylbenzo [1,2-<i>b</i>:5,4-<i>b</i>′]-Dithiophene and -Diselenophene (<i>iso</i>-DPh-BDXs)
  作者：Kazuo Takimiya、Yasushi Konda、Hideaki Ebata、Tetsuo Otsubo、Yoshihito Kunugi

  DOI：10.1080/15421400600698980

  日期：2006.10.1
• US9073938B2
  申请人：——

  公开号：US9073938B2

  公开（公告）日：2015-07-07