2,2’-([2,2’-bithiophene]-5,5’-diyl)diacetonitrile | 1239599-02-0

• 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: 2,2’-([2,2’-bithiophene]-5,5’-diyl)diacetonitrile
• 英文别名: 2,2'-([2,2'-bithiophene]-5,5'-diyl)diacetonitrile；5,5'-bis(cyanomethyl)-2,2'-bithiophene；2,2'-([2,2'-Bithiophene]-5,5'-diyl)diacetonitrile；2-[5-[5-(cyanomethyl)thiophen-2-yl]thiophen-2-yl]acetonitrile
• CAS: 1239599-02-0
• 化学式: C₁₂H₈N₂S₂
• 分子量: 244.341
• InChiKey: NYQNXLHAZCZDHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  47.58
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,2’-([2,2’-bithiophene]-5,5’-diyl)diacetonitrile 、 碳酸二甲酯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 生成
  参考文献：
  名称：

  ((Alkyloxy)carbonyl)cyanomethylene-Substituted Thienoquinoidal Compounds: a New Class of Soluble n-Channel Organic Semiconductors for Air-Stable Organic Field-Effect Transistors

  摘要：

  A new n-channel semiconductor class for organic field-effect transistors (OFETs) based on thienoquinoidal structures is reported. A newly employed terminal group, the ((alkyloxy)carbonyl)cyanomethylene moiety, plays two important roles in the thienoquinoidal compounds: i.e., as an electron-withdrawing group to keep the LUMO energy level sufficiently low for acting as an n-channel organic semiconductor and as a solubilizing group to facilitate solution processability. For the construction of this class of compounds, a new, straightforward synthetic method was established and applied to oligothienoquinoidal and fused thienoquinoidal systems. When both core and alkyl groups in the ester moiety were tuned, the thienoquinoidals exhibited good solubility, stability in the atmosphere, and electron-accepting properties, as well as solution processability. Solution-processed FETs based on the terthienoquinoid derivative with ((n-alkyloxy)carbonyl)cyanomethylene moieties exhibit good electron mobilities (mu similar to 0.015 cm(2) V-1 s(-1)) and I-on/I-off approximate to 10(5) under ambient conditions. Vapor-processed FETs using the benzodithienoquinoidal derivative showed similar n-channel FET characteristics.

  DOI：

  10.1021/ja103171y
• 作为产物：
  描述：

  sodium cyanide 、 5,5'-bis(chloromethyl)-2,2'-bithiophene 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以16%的产率得到2,2’-([2,2’-bithiophene]-5,5’-diyl)diacetonitrile
  参考文献：
  名称：

  ((Alkyloxy)carbonyl)cyanomethylene-Substituted Thienoquinoidal Compounds: a New Class of Soluble n-Channel Organic Semiconductors for Air-Stable Organic Field-Effect Transistors

  摘要：

  A new n-channel semiconductor class for organic field-effect transistors (OFETs) based on thienoquinoidal structures is reported. A newly employed terminal group, the ((alkyloxy)carbonyl)cyanomethylene moiety, plays two important roles in the thienoquinoidal compounds: i.e., as an electron-withdrawing group to keep the LUMO energy level sufficiently low for acting as an n-channel organic semiconductor and as a solubilizing group to facilitate solution processability. For the construction of this class of compounds, a new, straightforward synthetic method was established and applied to oligothienoquinoidal and fused thienoquinoidal systems. When both core and alkyl groups in the ester moiety were tuned, the thienoquinoidals exhibited good solubility, stability in the atmosphere, and electron-accepting properties, as well as solution processability. Solution-processed FETs based on the terthienoquinoid derivative with ((n-alkyloxy)carbonyl)cyanomethylene moieties exhibit good electron mobilities (mu similar to 0.015 cm(2) V-1 s(-1)) and I-on/I-off approximate to 10(5) under ambient conditions. Vapor-processed FETs using the benzodithienoquinoidal derivative showed similar n-channel FET characteristics.

  DOI：

  10.1021/ja103171y

文献信息

• A Thiophene Backbone Enables Two‐Dimensional Poly(arylene vinylene)s with High Charge Carrier Mobility
  作者：Yamei Liu、Heng Zhang、Hongde Yu、Zhongquan Liao、Silvia Paasch、Shunqi Xu、Ruyan Zhao、Eike Brunner、Mischa Bonn、Hai I. Wang、Thomas Heine、Mingchao Wang、Yiyong Mai、Xinliang Feng

  DOI：10.1002/anie.202305978

  日期：2023.8.28

  Linear conjugated polymers have attracted significant attention in organic electronics in recent decades. However, despite intrachain π‐delocalization, interchain hopping is their transport bottleneck. In contrast, two‐dimensional (2D) conjugated polymers, as represented by 2D π‐conjugated covalent organic frameworks (2D c‐COFs), can provide multiple conjugated strands to enhance the delocalization of charge carriers in space. Herein, we demonstrate the first example of thiophene‐based 2D poly(arylene vinylene)s (PAVs, 2DPAV‐BDT‐BT and 2DPAV‐BDT‐BP, BDT=benzodithiophene, BT=bithiophene, BP=biphenyl) via Knoevenagel polycondensation. Compared with 2DPAV‐BDT‐BP, the fully thiophene‐based 2DPAV‐BDT‐BT exhibits enhanced planarity and π‐delocalization with a small band gap (1.62 eV) and large electronic band dispersion, as revealed by the optical absorption and density functional calculations. Remarkably, temperature‐dependent terahertz spectroscopy discloses a unique band‐like transport and outstanding room‐temperature charge mobility for 2DPAV‐BDT‐BT (65 cm² V⁻¹ s⁻¹), which far exceeds that of the linear PAVs, 2DPAV‐BDT‐BP, and the reported 2D c‐COFs in the powder form. This work highlights the great potential of thiophene‐based 2D PAVs as candidates for high‐performance opto‐electronics.

  摘要近几十年来，线性共轭聚合物在有机电子学领域备受关注。然而，尽管存在链内π定位，链间跳变仍是其传输瓶颈。相比之下，以二维π共轭共价有机框架（2D c-COFs）为代表的二维（2D）共轭聚合物可以提供多条共轭链，从而增强电荷载流子在空间的脱ocal。在此，我们首次展示了通过克诺文纳格尔缩聚反应制备的噻吩基二维聚（芳基乙烯）（PAVs，2DPAV-BDT-BT 和 2DPAV-BDT-BP, BDT= 苯并二噻吩，BT= 联噻吩，BP= 联苯）。光吸收和密度泛函计算表明，与 2DPAV-BDT-BP 相比，完全基于噻吩的 2DPAV-BDT-BT 具有更强的平面性和 π 外定位性、更小的带隙（1.62 eV）和更大的电子带色散。值得注意的是，随温度变化的太赫兹光谱显示，2DPAV-BDT-BT 具有独特的带状传输和出色的室温电荷迁移率（65 cm2 V-1 s-1），远远超过线性 PAV、2DPAV-BDT-BP 和已报道的粉末状二维 c-COFs。这项工作凸显了噻吩基二维 PAV 作为高性能光电子候选材料的巨大潜力。
• Quinoidal Oligothiophenes with (Acyl)cyanomethylene Termini: Synthesis, Characterization, Properties, and Solution Processed n-Channel Organic Field-Effect Transistors
  作者：Yuki Suzuki、Masafumi Shimawaki、Eigo Miyazaki、Itaru Osaka、Kazuo Takimiya

  DOI：10.1021/cm102109p

  日期：2011.2.8

  A new class of oligothienoquinoidal derivatives with newly employed (acyl)cyanomethylene termini are reported. For the synthesis of (acyl)cyanomethylene-substituted thienoquinoidals, similar methods successfully employed for the synthesis of related dicyanomethylene- or ((alkyloxy)carbonyl)cyanomethylenc-substituted thienoquinoidals were not applicable, and thus a new synthetic route was developed. The introduced (acyl)cyanomethylene terminal groups act both as a solublizing group to facilitate solution processability and an electron-withdrawing group to keep the LUMO energy levels sufficiently low for n-channel organic semiconductors. The LUMO energy levels estimated from their reduction potential are similar to 4.2 eV below the vacuum level, which just falls in between those for the corresponding dicyanomethylene- and ((alkyloxy)carbonyl)cyanomethylene-substituted thienoquinoidals. This qualitatively agrees with the electron-withdrawing nature of the terminal groups; the order of the electron withdrawing nature is cyano- > acyl- > (alkyloxy)carbonyl- groups. Spin-coating chloroform solutions of (acyl)cyanomethylene-substituted thienoquinoidals gave homogeneous thin films on the Si/SiO2 substrates, and the thin films based on the terthienoquinoidal derivatives became highly crystalline upon thermal annealing. The annealed film acted as the active semiconducting channel in the FET devices under ambient conditions, and the electron mobilities extracted from the saturation regime were similar to 0.06 cm(2) V-1 s(-1). These n-channel FET characteristics are nearly the same or slightly better than those of the FETs based on the related ((alkyloxy)carbonyl)cyanomethylene-terminated terthienoquinoidal, indicating that the (acyl)cyanomethylene moiety is a useful terminal group on the thienoquinoidals for the development of soluble n-channel organic semiconductors.