S,S′-([2,2:5′,2″-terthiophene]-5,5″-diyl) diethanethioate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: S,S′-([2,2:5′,2″-terthiophene]-5,5″-diyl) diethanethioate
• 英文别名: 5,5''-bis(acetylthio)[2,2';5',2'']terthiophene；α,ω-bis(acetylthio)terthiophene；S-[5-[5-(5-acetylsulfanylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl] ethanethioate
• 化学式: C₁₆H₁₂O₂S₅
• 分子量: 396.6
• InChiKey: BJPRETIPVFQBGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,5-二(5-溴噻吩-2-基)噻吩 、 乙酰氯 在 正丁基锂 、 sulfur 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 17.5h， 以16%的产率得到S,S′-([2,2:5′,2″-terthiophene]-5,5″-diyl) diethanethioate
  参考文献：
  名称：

  Controlling the Thermoelectric Properties of Thiophene-Derived Single-Molecule Junctions

  摘要：

  Thermoelectrics are famously challenging to optimize, because of inverse coupling of the Seebeck coefficient and electrical conductivity, both of which control the thermoelectric power factor. Inorganic-organic interfaces provide a promising route for realization of the strong electrical and thermal asymmetries required for thermoelectrics. In this work, transport properties of inorganic-organic interfaces are probed and understood at the molecular scale using the STM-break junction measurement technique, theory, and a class of newly synthesized molecules. We synthesized a series of disubstituted thiophene derivatives varying the length of alkylthio-linkers and the number of thiophene rings. These molecules allow the systematic tuning of electronic resonances within the junction. We observed that these molecules have a decreasing Seebeck coefficient with increasing length of the alkyl chain, while oligothiophene junctions show an increasing Seebeck coefficient with length. We find that thiophene-Au junctions have significantly higher Seebeck coefficients, compared to benzenedithiol (in the range of 7-15 mu V/K). A minimal tight-binding model, including a gateway state associated with the S-Au bond, captures and explains both trends. This work identifies S-Au gateway states as being important and potentially tunable features of junction electronic structure for enhancing the power factor of organic/inorganic interfaces.

  DOI：

  10.1021/cm504254n

文献信息

• Electron transport in networks of gold nanoparticles connected by oligothiophene molecular wires
  作者：Shin-ichi Taniguchi、Masaru Minamoto、Michio M. Matsushita、Tadashi Sugawara、Yuzo Kawada、Donald Bethell

  DOI：10.1039/b604732g

  日期：——

  Network structures made of π-conjugated molecular wires of oligothiophene 3mer, or 9mer carrying thiol groups at α,ω-positions, and gold nanoparticles with average diameter of 4 nm were prepared on interdigitated gold electrodes. Observation of the resultant assemblies by means of FE-SEM and TEM revealed that the gold nanoparticles were connected by π-molecular wires to form a network. The networks exhibited thermally activated electron transport at room temperature with activation energies of 21and 45 meV for 3mer- and 9mer-networks, respectively, and these values were almost the same as those of networks connected with non-conjugated molecules having similar lengths. However, the activation energy became very small (∼0.1 meV) at temperatures lower than 30 K and non-linear current–voltage characteristics (I ∝ V3) appeared in π-conjugated networks at 4.2 K. These results suggest that the gold nanoparticles in the networks work as Coulomb islands and the temperature-independent behavior at lower temperatures can be interpreted in terms of a co-tunneling mechanism.

  在相互咬合的金电极上，制备了由寡噻吩 3 聚物或 9 聚物（在 α、ω 位置带有硫醇基团）的 π 共轭分子线和平均直径为 4 纳米的金纳米粒子组成的网络结构。通过 FE-SEM 和 TEM 对所制备的组件进行观察发现，金纳米粒子通过 π 分子线连接形成网络。这些网络在室温下表现出热启动电子传输，3 聚体网络和 9 聚体网络的活化能分别为 21 和 45 meV，这些数值与长度相似的非共轭分子连接的网络几乎相同。然而，在温度低于 30 K 时，活化能变得非常小（∼0.1 meV），并且在 4.2 K 时，π-共轭网络出现了非线性电流-电压特性（I∝V3）。这些结果表明，网络中的金纳米粒子作为库仑岛起作用，并且在较低温度下的行为与温度无关，可以用共隧道机制来解释。
• Controlling the Thermoelectric Properties of Thiophene-Derived Single-Molecule Junctions
  作者：William B. Chang、Cheng-Kang Mai、Michele Kotiuga、Jeffrey B. Neaton、Guillermo C. Bazan、Rachel A. Segalman

  DOI：10.1021/cm504254n

  日期：2014.12.23

  Thermoelectrics are famously challenging to optimize, because of inverse coupling of the Seebeck coefficient and electrical conductivity, both of which control the thermoelectric power factor. Inorganic-organic interfaces provide a promising route for realization of the strong electrical and thermal asymmetries required for thermoelectrics. In this work, transport properties of inorganic-organic interfaces are probed and understood at the molecular scale using the STM-break junction measurement technique, theory, and a class of newly synthesized molecules. We synthesized a series of disubstituted thiophene derivatives varying the length of alkylthio-linkers and the number of thiophene rings. These molecules allow the systematic tuning of electronic resonances within the junction. We observed that these molecules have a decreasing Seebeck coefficient with increasing length of the alkyl chain, while oligothiophene junctions show an increasing Seebeck coefficient with length. We find that thiophene-Au junctions have significantly higher Seebeck coefficients, compared to benzenedithiol (in the range of 7-15 mu V/K). A minimal tight-binding model, including a gateway state associated with the S-Au bond, captures and explains both trends. This work identifies S-Au gateway states as being important and potentially tunable features of junction electronic structure for enhancing the power factor of organic/inorganic interfaces.