(E,E)-1,4-bis[4-(bromomethyl)styryl]benzene | 874486-68-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E,E)-1,4-bis[4-(bromomethyl)styryl]benzene
• 英文别名: (E,E)-1,4-bis[p-bromomethylstyryl]benzene
• CAS: 874486-68-7
• 化学式: C₂₄H₂₀Br₂
• 分子量: 468.231
• InChiKey: JGBDTYBKTKZVHN-KQQUZDAGSA-N

物化性质

• 熔点：
  >280 °C
• 沸点：
  560.3±50.0 °C(Predicted)
• 密度：
  1.487±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.82
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (E,E)-1,4-bis[4-(bromomethyl)styryl]benzene 、 potassium thioacetate 在 碘 作用下， 以 N-甲基吡咯烷酮 、 甲苯 为溶剂， 反应 14.0h， 以57%的产率得到(E,E)-1,4-bis[4-(acetylsulfanylmethyl)styryl]benzene
  参考文献：
  名称：

  Synthetic protocols and building blocks for molecular electronics

  摘要：

  Simple and readily accessible aryl bromides are useful building blocks for thiol end-capped molecular wires. Thus, 4-bromophenyl tert-butyl sulfide and 1-bromo-4-(methoxymethyl)benzene serve as precursors for a variety of oligo(phenylenevinylene) and oligo(phenyleneethynylene) wires via efficient synthetic transformations as presented in this paper. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.106
• 作为产物：
  描述：

  4-溴基苄基甲醚 在 正丁基锂 、 三甲基溴硅烷 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 正己烷 、 氯苯 为溶剂， 反应 34.75h， 生成 (E,E)-1,4-bis[4-(bromomethyl)styryl]benzene
  参考文献：
  名称：

  Synthetic protocols and building blocks for molecular electronics

  摘要：

  Simple and readily accessible aryl bromides are useful building blocks for thiol end-capped molecular wires. Thus, 4-bromophenyl tert-butyl sulfide and 1-bromo-4-(methoxymethyl)benzene serve as precursors for a variety of oligo(phenylenevinylene) and oligo(phenyleneethynylene) wires via efficient synthetic transformations as presented in this paper. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.106

文献信息

• Synthetic protocols and building blocks for molecular electronics
  作者：Nicolai Stuhr-Hansen、Jakob Kryger Sørensen、Kasper Moth-Poulsen、Jørn Bolstad Christensen、Thomas Bjørnholm、Mogens Brøndsted Nielsen

  DOI：10.1016/j.tet.2005.09.106

  日期：2005.12

  Simple and readily accessible aryl bromides are useful building blocks for thiol end-capped molecular wires. Thus, 4-bromophenyl tert-butyl sulfide and 1-bromo-4-(methoxymethyl)benzene serve as precursors for a variety of oligo(phenylenevinylene) and oligo(phenyleneethynylene) wires via efficient synthetic transformations as presented in this paper. (c) 2005 Elsevier Ltd. All rights reserved.
• Fabrication of Steady Junctions Consisting of α,ω-Bis(thioacetate) Oligo(<i>p</i>-phenylene vinylene)s in Nanogap Electrodes
  作者：Tien-Tzu Liang、Yasuhisa Naitoh、Masayo Horikawa、Takao Ishida、Wataru Mizutani

  DOI：10.1021/ja062561h

  日期：2006.10.1

  For obtaining molecular devices using metal-molecule-metal junctions, it is necessary to fabricate a steady conductive bridge-structure; that is stable chemical bonds need to be established from a single conductive molecule to two facing electrodes. In the present paper, we show that the steadiness of a conductive bridge-structure depends on the molecular structure of the bridge molecule for nanogap junctions using three types of modified oligo(phenylene vinylene)s (OPVs): alpha,omega-bis(thioacetate) oligo(phenylene vinylene) (OPV1), alpha,omega-bis(methylthioacetate) oligo(phenylene vinylene) (OPV2), and OPV2 consisting of ethoxy side chains (OPV3). We examined the change in resistance between the molecule-bridged junction and a bare junction in each of the experimental Au-OPV-Au junctions to confirm whether molecules formed steady bridges. Herein, the outcomes of whether molecules formed steady bridges were defined in terms of three types of result; successful, possible and failure. We define the ratio of the number of successful junctions to the total number of experimental junctions as successful rate. A 60% successful rate for OPV3 was higher than for the other two molecules whose successful rates were estimated to be similar to 10%. We propose that conjugated molecules consisting of methylthioacetate termini and short alkoxy side chains are well suited for fabricating a steady conductive bridge-structure between two facing electrodes.