2-Trimethylsilylethyl 4-[2-[3,7-dicyano-2,6-bis(dihexylamino)-4-[2-[4-(2-trimethylsilylethylsulfanylcarbothioyl)phenyl]ethynyl]furo[2,3-f][1]benzofuran-8-yl]ethynyl]benzenecarbodithioate | 1613333-79-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-Trimethylsilylethyl 4-[2-[3,7-dicyano-2,6-bis(dihexylamino)-4-[2-[4-(2-trimethylsilylethylsulfanylcarbothioyl)phenyl]ethynyl]furo[2,3-f][1]benzofuran-8-yl]ethynyl]benzenecarbodithioate
• 英文别名: 2-trimethylsilylethyl 4-[2-[3,7-dicyano-2,6-bis(dihexylamino)-4-[2-[4-(2-trimethylsilylethylsulfanylcarbothioyl)phenyl]ethynyl]furo[2,3-f][1]benzofuran-8-yl]ethynyl]benzenecarbodithioate
• CAS: 1613333-79-1
• 化学式: C₆₄H₈₆N₄O₂S₄Si₂
• 分子量: 1127.85
• InChiKey: GNUAMNIGZMMHCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.15
• 重原子数：
  76
• 可旋转键数：
  36
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  195
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4-ethynyl(dithiobenzoic) acid 2-(trimethylsilyl)ethyl ester 、 2,6-bis(N,N-dihexylamino)-4,8-diiodobenzo[1,2-b:4,5-b’]difuran-3,7-dicarbonitrile 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 3.0h， 以29%的产率得到2-Trimethylsilylethyl 4-[2-[3,7-dicyano-2,6-bis(dihexylamino)-4-[2-[4-(2-trimethylsilylethylsulfanylcarbothioyl)phenyl]ethynyl]furo[2,3-f][1]benzofuran-8-yl]ethynyl]benzenecarbodithioate
  参考文献：
  名称：

  Regulating a Benzodifuran Single Molecule Redox Switch via Electrochemical Gating and Optimization of Molecule/Electrode Coupling

  摘要：

  We report a novel strategy for the regulation of charge transport through single molecule junctions via the combination of external stimuli of electrode potential, internal modulation of molecular structures, and optimization of anchoring groups. We have designed redox-active benzodifuran (BDF) compounds as functional electronic units to fabricate metal-molecule-metal (m-M-m) junction devices by scanning tunneling microscopy (STM) and mechanically controllable break junctions (MCBJ). The conductance of thiol-terminated BDF can be tuned by changing the electrode potentials showing clearly an off/on/off single molecule redox switching effect. To optimize the response, a BDF molecule tailored with carbodithioate (-CS2(-)) anchoring groups was synthesized. Our studies show that replacement of thiol by carbodithioate not only enhances the junction conductance but also substantially improves the switching effect by enhancing the on/off ratio from 2.5 to 8.

  DOI：

  10.1021/ja5034606

文献信息

• Regulating a Benzodifuran Single Molecule Redox Switch via Electrochemical Gating and Optimization of Molecule/Electrode Coupling
  作者：Zhihai Li、Hui Li、Songjie Chen、Toni Froehlich、Chenyi Yi、Christian Schönenberger、Michel Calame、Silvio Decurtins、Shi-Xia Liu、Eric Borguet

  DOI：10.1021/ja5034606

  日期：2014.6.25

  We report a novel strategy for the regulation of charge transport through single molecule junctions via the combination of external stimuli of electrode potential, internal modulation of molecular structures, and optimization of anchoring groups. We have designed redox-active benzodifuran (BDF) compounds as functional electronic units to fabricate metal-molecule-metal (m-M-m) junction devices by scanning tunneling microscopy (STM) and mechanically controllable break junctions (MCBJ). The conductance of thiol-terminated BDF can be tuned by changing the electrode potentials showing clearly an off/on/off single molecule redox switching effect. To optimize the response, a BDF molecule tailored with carbodithioate (-CS2(-)) anchoring groups was synthesized. Our studies show that replacement of thiol by carbodithioate not only enhances the junction conductance but also substantially improves the switching effect by enhancing the on/off ratio from 2.5 to 8.