1,4-bis[(4-acetylthiophenyl)ethynyl]naphthalene | 1364344-60-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-bis[(4-acetylthiophenyl)ethynyl]naphthalene
• 英文别名: S,S'-((naphthalene-1,4-diylbis (ethyne-2,1-diyl))bis(4,1-phenylene)) diethanethioate
• CAS: 1364344-60-4
• 化学式: C₃₀H₂₀O₂S₂
• 分子量: 476.62
• InChiKey: QBXUJOSGPRYBCR-UHFFFAOYSA-N

物化性质

• 沸点：
  670.7±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.92
• 重原子数：
  34.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1,4-bis(trimethylsilylethynyl)naphthalene 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium fluoride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 生成 1,4-bis[(4-acetylthiophenyl)ethynyl]naphthalene
  参考文献：
  名称：

  一锅法合成低聚（亚芳基-乙炔基）-分子线及其在进一步验证分子电路定律中的应用†

  摘要：

  通过受保护的双（炔烃）Me 3 SiC≡CArC≡CSiMe 3 (Ar = 2,5-噻吩基、1,4-萘基、9,10-蒽）和随后的 Sonogashira 与S-（4-碘苯基）乙硫醇盐、4-碘硫代苯甲醚或 5-溴-3,3-二甲基-描述了2,3-二氢苯并[ b ]噻吩。现场的去甲硅烷化避免了对敏感末端二炔烃 (HC≡CArC≡CH) 的操作，而所提出的一般方法通过避免末端的多步制备和纯化，与基于芳基二卤化物 (XArX) 偶联的替代合成策略相比具有一些优势炔烃S- (4-ethynylphenyl) ethanethiolate, 4-ethynylthioanisole 和 5-ethynyl 3,3-dimethyl-2,3-dihydrobenzo[ b]噻吩。使用扫描隧道显微镜断裂连接 (STM-BJ) 方法确定了所得硫醇盐或硫醚官能化 OAE 分子线的分子电导。尽管分子长度相当相似

  DOI：

  10.1071/ch21235

文献信息

• Correlations between Molecular Structure and Single-Junction Conductance: A Case Study with Oligo(phenylene-ethynylene)-Type Wires
  作者：Veerabhadrarao Kaliginedi、Pavel Moreno-García、Hennie Valkenier、Wenjing Hong、Víctor M. García-Suárez、Petra Buiter、Jelmer L. H. Otten、Jan C. Hummelen、Colin J. Lambert、Thomas Wandlowski

  DOI：10.1021/ja211555x

  日期：2012.3.21

  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.