(E,E)-1,4-bis[4-(acetylsulfanylmethyl)styryl]benzene

• 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-(acetylsulfanylmethyl)styryl]benzene
• 英文别名: (E,E)-1,4-bis[4-(S-acetylthiomethyl)styryl]benzene；(E,E)-1,4-bis[4'-methyl(thioacetyl)styryl]benzene；S-[[4-[(E)-2-[4-[(E)-2-[4-(acetylsulfanylmethyl)phenyl]ethenyl]phenyl]ethenyl]phenyl]methyl] ethanethioate
• 化学式: C₂₈H₂₆O₂S₂
• 分子量: 458.645
• InChiKey: LNSFPIZZQKVIID-FIFLTTCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-溴甲基苯甲醛 在 乙醇锂 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.75h， 生成 (E,E)-1,4-bis[4-(acetylsulfanylmethyl)styryl]benzene
  参考文献：
  名称：

  Single-Molecule Charge-Transport Measurements that Reveal Technique-Dependent Perturbations

  摘要：

  We compare scanning tunneling microscopy (STM) imaging with single-molecule conductive atomic force microscopy (C-AFM)measurements by probing a series of structurally related thiol-terminated oligo(phenylenevinylene)s (OPVs) designed to have unique charge-transport signatures. When one or two methylene spacers are inserted between the thiol points of attachment and the OPV core, a systematic reduction in the imaged molecular transconductance and the current transmitted through a metal-moleculemetal junction containing the molecule is observed, indicating good agreement between STM and C-AFM measurements. However, a structure where the OPV backbone is interrupted by a [2.2] paracyclophane core has a low molecular transconductance, as determined from STM images, and a high measured single-molecule conductance. This apparent disconnect can be understood by comparing the calculated molecular orbital topology of the OPV with one thiol bound to a gold surface (the geometry in the STM experiment) with the topology of the molecule with both thiol termini bound to gold (relevant to C-AFM). In the former case, a single contact splits low-lying molecular orbitals into two discrete fragments, and in the latter case, molecular orbitals that span the entire molecule are observed. Although the difference in observed conductance between the two different measurements is resolved, the overall set of observations highlights the importance of using combined techniques to better characterize charge-transport properties relevant to molecular electronics.

  DOI：

  10.1021/ja062898j

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.
• Single-Molecule Charge-Transport Measurements that Reveal Technique-Dependent Perturbations
  作者：Dwight S. Seferos、Amy Szuchmacher Blum、James G. Kushmerick、Guillermo C. Bazan

  DOI：10.1021/ja062898j

  日期：2006.8.1

  We compare scanning tunneling microscopy (STM) imaging with single-molecule conductive atomic force microscopy (C-AFM)measurements by probing a series of structurally related thiol-terminated oligo(phenylenevinylene)s (OPVs) designed to have unique charge-transport signatures. When one or two methylene spacers are inserted between the thiol points of attachment and the OPV core, a systematic reduction in the imaged molecular transconductance and the current transmitted through a metal-moleculemetal junction containing the molecule is observed, indicating good agreement between STM and C-AFM measurements. However, a structure where the OPV backbone is interrupted by a [2.2] paracyclophane core has a low molecular transconductance, as determined from STM images, and a high measured single-molecule conductance. This apparent disconnect can be understood by comparing the calculated molecular orbital topology of the OPV with one thiol bound to a gold surface (the geometry in the STM experiment) with the topology of the molecule with both thiol termini bound to gold (relevant to C-AFM). In the former case, a single contact splits low-lying molecular orbitals into two discrete fragments, and in the latter case, molecular orbitals that span the entire molecule are observed. Although the difference in observed conductance between the two different measurements is resolved, the overall set of observations highlights the importance of using combined techniques to better characterize charge-transport properties relevant to molecular electronics.