1,4-benzenedicarbodithioic acid 2-(trimethlysilyl)ethyl ester | 1228173-20-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,4-benzenedicarbodithioic acid 2-(trimethlysilyl)ethyl ester
• CAS: 1228173-20-3
• 化学式: C₁₈H₃₀S₄Si₂
• 分子量: 430.871
• InChiKey: WMRTYPCURWIVGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.18
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (2-溴乙基)三甲硅烷 、 1,4-对二氯苄 在 sodium methylate 、 sulfur 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以4.5%的产率得到1,4-benzenedicarbodithioic acid 2-(trimethlysilyl)ethyl ester
  参考文献：
  名称：

  Optimizing Single-Molecule Conductivity of Conjugated Organic Oligomers with Carbodithioate Linkers

  摘要：

  In molecular electronics, the linker group, which attaches the functional molecular core to the electrode, plays a crucial role in determining the overall conductivity of the molecular junction. While much focus has been placed on optimizing molecular core conductivity, there have been relatively few attempts at designing optimal linker groups to metallic or semiconducting electrodes. The vast majority of molecular electronic studies use thiol linker groups; work probing alternative amine linker systems has only recently been explored. Here, we probe single-molecule conductances in phenylene-ethynylene molecules terminated with thiol and carbodithioate linkers, experimentally using STM break-junction methods and theoretically using a nonequilibrium Green's function approach. Experimental studies demonstrate that the carbodithioate linker augments electronic coupling to the metal electrode and lowers the effective barrier for charge transport relative to the conventional thiol linker, thus enhancing the conductance of the linker-phenylene-ethynylene-linker unit; these data underscore that phenylene-ethynylene-based structures are more highly conductive than originally appreciated in molecular electronics applications. The theoretical analysis shows that the nature of sulfur hybridization in these species is responsible for the order-of-magnitude increased conductance in carbodithioate-terminated systems relative to identical conjugated structures that feature classic thiol linkers, independent of the mechanism of charge transport. Interestingly, in these systems, the tunneling current is not dominated by the frontier molecular orbitals. While barriers > k(B)T to produce the low beta values seen in our experiments. Taken together, these experimental and theoretical studies indicate a promising role for carbodithioate-based connectivity in molecular-scale electronics applications involving metallic and semiconducting electrodes.

  DOI：

  10.1021/ja909559m