(E,E)-1,4-bis[4-(tert-butylsulfanyl)styryl]benzene | 500530-77-8

• 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-(tert-butylsulfanyl)styryl]benzene
• 英文别名: (E,E)-1,4-bis[4-(tert-butylthio)styryl]benzene；(E,E)-1,4-bis(4-tert-butylthio-styryl)benzene；1,4-bis[(E)-2-(4-tert-butylsulfanylphenyl)ethenyl]benzene
• CAS: 500530-77-8
• 化学式: C₃₀H₃₄S₂
• 分子量: 458.732
• InChiKey: QILGOFZMOIFYLZ-PHEQNACWSA-N

物化性质

• 沸点：
  598.6±50.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 (E,E)-1,4-bis[4-(tert-butylsulfanyl)styryl]benzene 在 溴 、 溶剂黄146 作用下， 反应 2.0h， 生成 1,4-bis(4-acetylthio-styryl)benzene
  参考文献：
  名称：

  新的十字形结构：向配位诱导的单分子开关

  摘要：

  新的十字形结构1 - 4合成以研究由分子与电极表面之间的相互作用产生的新的单分子转换机制。这些分子关键是由两个杆型子结构，即一个低聚亚苯基亚乙烯基和一个低聚亚苯基乙炔基。尽管低聚苯撑乙烯撑棒被乙酰基保护的硫锚定基团官能化，但低聚苯撑乙炔基棒提供了末端吡啶单元。假设的开关机制应归因于吡啶单元与电极表面的电化学势相关配位。低聚亚苯基亚乙烯基亚结构的组装基于维蒂希反应，而其垂直的低聚亚苯基乙炔基棒则通过Sonogashira-Hagihara偶联反应进行组装。分子十字形的初步运输研究图2和图4在液体环境中的机械可控制的断裂连接处显示了通过末端硫官能化的低聚亚苯基亚乙烯基棒在两个金电极之间捕获单分子。

  DOI：

  10.1021/jo7013998
• 作为产物：
  描述：

  1-溴-4-(叔丁基磺酰基)苯 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 (E,E)-1,4-bis[4-(tert-butylsulfanyl)styryl]benzene
  参考文献：
  名称：

  Novel Synthesis of Protected Thiol End-Capped Stilbenes and Oligo(phenylenevinylene)s (OPVs)

  摘要：

  The first general procedures for preparation of thiol end-capped stilbenes and oligo(phenylene-vinylene)s (OPVs) with tert-butyl- and acetyl-protected thiol termini have been developed. These reactions proceed via Br/Li exchange, McMurry, and Wittig-type reactions. The thiol functionality is protected against strong basic and acidic reaction conditions as a t-Bu sulfide. As a key point in the method, reprotection of the thiol group is accomplished by means of acetyl chloride and boron tribromide. The novel strategy forms the basis for stepwise introduction of 4-mercaptostyryl units in OPVs. The new mono-, di-, and trimercapto OPVs have potential applications as one, two, and three terminal molecular devices in gold nanoparticle clusters, self-assembled monolayers, and optoelectronic devices.

  DOI：

  10.1021/jo0263770

文献信息

• Novel Synthesis of Protected Thiol End-Capped Stilbenes and Oligo(phenylenevinylene)s (OPVs)
  作者：Nicolai Stuhr-Hansen、Jørn B. Christensen、Niels Harrit、Thomas Bjørnholm

  DOI：10.1021/jo0263770

  日期：2003.2.1

  The first general procedures for preparation of thiol end-capped stilbenes and oligo(phenylene-vinylene)s (OPVs) with tert-butyl- and acetyl-protected thiol termini have been developed. These reactions proceed via Br/Li exchange, McMurry, and Wittig-type reactions. The thiol functionality is protected against strong basic and acidic reaction conditions as a t-Bu sulfide. As a key point in the method, reprotection of the thiol group is accomplished by means of acetyl chloride and boron tribromide. The novel strategy forms the basis for stepwise introduction of 4-mercaptostyryl units in OPVs. The new mono-, di-, and trimercapto OPVs have potential applications as one, two, and three terminal molecular devices in gold nanoparticle clusters, self-assembled monolayers, and optoelectronic devices.
• New Cruciform Structures:  Toward Coordination Induced Single Molecule Switches
  作者：Sergio Grunder、Roman Huber、Viviana Horhoiu、Maria Teresa González、Christian Schönenberger、Michel Calame、Marcel Mayor

  DOI：10.1021/jo7013998

  日期：2007.10.1

  New cruciform structures 1−4 were synthesized to investigate a new single molecule switching mechanism arising from the interplay between the molecule and the electrode surface. These molecular cruxes consist of two rod-type substructures, namely an oligophenylenevinylene and an oligophenyleneethynyl. While the oligophenylenevinylene rods are functionalized with acetyl protected sulfur anchor groups

  新的十字形结构1 - 4合成以研究由分子与电极表面之间的相互作用产生的新的单分子转换机制。这些分子关键是由两个杆型子结构，即一个低聚亚苯基亚乙烯基和一个低聚亚苯基乙炔基。尽管低聚苯撑乙烯撑棒被乙酰基保护的硫锚定基团官能化，但低聚苯撑乙炔基棒提供了末端吡啶单元。假设的开关机制应归因于吡啶单元与电极表面的电化学势相关配位。低聚亚苯基亚乙烯基亚结构的组装基于维蒂希反应，而其垂直的低聚亚苯基乙炔基棒则通过Sonogashira-Hagihara偶联反应进行组装。分子十字形的初步运输研究图2和图4在液体环境中的机械可控制的断裂连接处显示了通过末端硫官能化的低聚亚苯基亚乙烯基棒在两个金电极之间捕获单分子。
• 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.