bis[4-((4-tert-butylthiophenyl)ethynyl)phenyl]acetylene | 1364344-52-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: bis[4-((4-tert-butylthiophenyl)ethynyl)phenyl]acetylene
• CAS: 1364344-52-4
• 化学式: C₃₈H₃₄S₂
• 分子量: 554.82
• InChiKey: NMPYRCUSRCKHER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.67
• 重原子数：
  40.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  bis[4-((4-tert-butylthiophenyl)ethynyl)phenyl]acetylene 、 乙酰氯 在 三溴化硼 作用下， 以 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 96.0h， 以43%的产率得到bis[4-((4-acetylthiophenyl)ethynyl)phenyl]acetylene
  参考文献：
  名称：

  Correlations between Molecular Structure and Single-Junction Conductance: A Case Study with Oligo(phenylene-ethynylene)-Type Wires

  摘要：

  The charge transport characteristics of 11 tailor-made dithiol-terminated oligo(phenylene-ethynylene) (OPE)-type molecules attached to two gold electrodes were studied at a solid/liquid interface in a combined approach using an STM break junction (STM-BJ) and a mechanically controlled break junction (MCBJ) setup. We designed and characterized 11 structurally distinct dithiol-terminated OPE-type molecules with varied length and HOMO/LUMO energy. Increase of the molecular length and/or of the HOMO-LUMO gap leads to a decrease of the single-junction conductance of the linearly conjugate acenes. The experimental data and simulations suggest a nonresonant tunneling mechanism involving hole transport through the molecular HOMO, with a decay constant beta = 3.4 +/- 0.1 nm(-1) and a contact resistance R-c = 40 k Omega per Au-S bond. The introduction of a cross-conjugated anthraquinone or a dihydroanthracene central unit results in lower conductance values, which are attributed to a destructive quantum interference phenomenon for the former and a broken pi-conjugation for the latter. The statistical analysis of conductance-distance and current-voltage traces revealed details of evolution and breaking of molecular junctions. In particular, we explored the effect of stretching rate and junction stability. We compare our experimental results with DFT calculations using the ab initio code SMEAGOL and discuss how the structure of the molecular wires affects the conductance values.

  DOI：

  10.1021/ja211555x
• 作为产物：
  描述：

  ((4-(tert-butylthio)phenyl)ethynyl)triisopropylsilane 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 生成 bis[4-((4-tert-butylthiophenyl)ethynyl)phenyl]acetylene
  参考文献：
  名称：

  Correlations between Molecular Structure and Single-Junction Conductance: A Case Study with Oligo(phenylene-ethynylene)-Type Wires

  摘要：

  The charge transport characteristics of 11 tailor-made dithiol-terminated oligo(phenylene-ethynylene) (OPE)-type molecules attached to two gold electrodes were studied at a solid/liquid interface in a combined approach using an STM break junction (STM-BJ) and a mechanically controlled break junction (MCBJ) setup. We designed and characterized 11 structurally distinct dithiol-terminated OPE-type molecules with varied length and HOMO/LUMO energy. Increase of the molecular length and/or of the HOMO-LUMO gap leads to a decrease of the single-junction conductance of the linearly conjugate acenes. The experimental data and simulations suggest a nonresonant tunneling mechanism involving hole transport through the molecular HOMO, with a decay constant beta = 3.4 +/- 0.1 nm(-1) and a contact resistance R-c = 40 k Omega per Au-S bond. The introduction of a cross-conjugated anthraquinone or a dihydroanthracene central unit results in lower conductance values, which are attributed to a destructive quantum interference phenomenon for the former and a broken pi-conjugation for the latter. The statistical analysis of conductance-distance and current-voltage traces revealed details of evolution and breaking of molecular junctions. In particular, we explored the effect of stretching rate and junction stability. We compare our experimental results with DFT calculations using the ab initio code SMEAGOL and discuss how the structure of the molecular wires affects the conductance values.

  DOI：

  10.1021/ja211555x