2-trimethylstannyl-3-decylthiophene | 1263426-40-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 金属芳基
• 英文名称: 2-trimethylstannyl-3-decylthiophene
• 英文别名: 2-(trimethylstannyl)-3-(n-decyl)thiophene；(3-Decyl-2-thienyl)trimethylstannane；(3-decylthiophen-2-yl)-trimethylstannane
• CAS: 1263426-40-9
• 化学式: C₁₇H₃₂SSn
• 分子量: 387.217
• InChiKey: IYVGSKZSIFQEFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-trimethylstannyl-3-decylthiophene 、 1,3-dibromo-5-(n-decyl)thieno[3,4-c]pyrrole-4,6-dione 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以73%的产率得到1,3-bis[3-(n-decyl)thien-2-yl]-5-(n-decyl)thieno[3,4-c]pyrrole-4,6-dione
  参考文献：
  名称：

  Thieno[3,4-c]pyrrole-4,6-dione-Based Polymer Semiconductors: Toward High-Performance, Air-Stable Organic Thin-Film Transistors

  摘要：

  We report a new,p-type semiconducting polymer family based on the thieno[3,4-c]pyrrole-4,6-dione (TPD) building block, which exhibits good processability as well as good mobility and lifetime stability in thin-film transistors (TFTs). TPD homopolymer P1 was synthesized via Yamamoto coupling, whereas copolymers P2-P8 were synthesized via Stile coupling. All of these polymers were characterized by chemical analysis as well as thermal analysis, optical spectroscopy, and cyclic voltammetry. P2-P7 have lower-lying HOMOs than does P3HT by 0.24-0.57 eV, depending on the donor counits, and exhibit large oscillator strengths in the visible region with similar optical band gaps throughout the series (similar to 1.80 eV). The electron-rich character of the dialkoxybithiophene counits in P8 greatly compresses the band gap, resulting in the lowest E-g(opt) in the series (1.66 eV), but also raising the HOMO energy to -5.11 eV. Organic thin-film transistor (OTFT) electrical characterization indicates that device performance is very sensitive to the oligothiophene conjugation length, but also to the solubilizing side chain substituEnts (length, positional pattern). The corresponding thin-film microstructures and morphologies were investigated by XRD and AFM to correlate with the OTFT performance. By strategically varying the oligothiophene donor conjugation length and optimizing the solubilizing side chains, a maximum OTFT hole mobility of similar to 0.6 cm(2) V-1 s(-1) is achieved for P4-based devices. OTFT environmental (storage) and operational (bias) stability in ambient was investigated, and enhanced performance is observed due to the low-lying HOMOs. These results indicate that the TPD is an excellent building block for constructing high-performance polymers for p-type transistor applications due to the excellent processability, substantial hole mobility, and good device stability.

  DOI：

  10.1021/ja205398u
• 作为产物：
  描述：

  三甲基氯化锡 、 3-癸基噻吩 在 C₄H₉Li 作用下， 以 四氢呋喃 为溶剂， 生成 2-trimethylstannyl-3-decylthiophene
  参考文献：
  名称：

  用于场效应晶体管的基于联噻吩酰亚胺的聚合物半导体：合成、结构-性质相关性、载流子极性和器件稳定性

  摘要：

  开发具有良好加工性和优异器件环境稳定性的新型高迁移率聚合物半导体对于有机电子产品至关重要。我们报告了用于有机场效应晶体管 (OFET) 的一系列新的基于联噻吩酰亚胺 (BTI) 的聚合物的合成、表征、操纵电荷载流子极性和器件空气稳定性。通过增加供体共聚单体单元的共轭长度，从单噻吩 (P1) 到联噻吩 (P2) 再到四噻吩 (P3)，电子传输能力降低，而空穴传输能力增加。与电子迁移率为 10(-2) cm(2) V(-1) s(-1) 的 BTI 均聚物 P(BTimR) 相比，共聚物 P1 是双极性的，空穴和电子迁移率为 ~10(-4 ) 厘米(2) V(-1) s(-1), 而 P2 和 P3 的空穴迁移率分别为~10(-3) 和~10(-2) cm(2) V(-1) s(-1)。还研究了 P(BTimR) 均聚物 M(n) 对薄膜形态和器件性能的影响。高 M(n) 批次 P(BTimR)-H

  DOI：

  10.1021/ja107678m

文献信息

• Thieno[3,4-<i>c</i>]pyrrole-4,6-dione-Based Polymer Semiconductors: Toward High-Performance, Air-Stable Organic Thin-Film Transistors
  作者：Xugang Guo、Rocio Ponce Ortiz、Yan Zheng、Myung-Gil Kim、Shiming Zhang、Yan Hu、Gang Lu、Antonio Facchetti、Tobin J. Marks

  DOI：10.1021/ja205398u

  日期：2011.8.31

  We report a new,p-type semiconducting polymer family based on the thieno[3,4-c]pyrrole-4,6-dione (TPD) building block, which exhibits good processability as well as good mobility and lifetime stability in thin-film transistors (TFTs). TPD homopolymer P1 was synthesized via Yamamoto coupling, whereas copolymers P2-P8 were synthesized via Stile coupling. All of these polymers were characterized by chemical analysis as well as thermal analysis, optical spectroscopy, and cyclic voltammetry. P2-P7 have lower-lying HOMOs than does P3HT by 0.24-0.57 eV, depending on the donor counits, and exhibit large oscillator strengths in the visible region with similar optical band gaps throughout the series (similar to 1.80 eV). The electron-rich character of the dialkoxybithiophene counits in P8 greatly compresses the band gap, resulting in the lowest E-g(opt) in the series (1.66 eV), but also raising the HOMO energy to -5.11 eV. Organic thin-film transistor (OTFT) electrical characterization indicates that device performance is very sensitive to the oligothiophene conjugation length, but also to the solubilizing side chain substituEnts (length, positional pattern). The corresponding thin-film microstructures and morphologies were investigated by XRD and AFM to correlate with the OTFT performance. By strategically varying the oligothiophene donor conjugation length and optimizing the solubilizing side chains, a maximum OTFT hole mobility of similar to 0.6 cm(2) V-1 s(-1) is achieved for P4-based devices. OTFT environmental (storage) and operational (bias) stability in ambient was investigated, and enhanced performance is observed due to the low-lying HOMOs. These results indicate that the TPD is an excellent building block for constructing high-performance polymers for p-type transistor applications due to the excellent processability, substantial hole mobility, and good device stability.
• Bithiophene-Imide-Based Polymeric Semiconductors for Field-Effect Transistors: Synthesis, Structure−Property Correlations, Charge Carrier Polarity, and Device Stability
  作者：Xugang Guo、Rocio Ponce Ortiz、Yan Zheng、Yan Hu、Yong-Young Noh、Kang-Jun Baeg、Antonio Facchetti、Tobin J. Marks

  DOI：10.1021/ja107678m

  日期：2011.2.9

  slightly lower than that of state-of-the-art n-type polymer semiconductors. However, the high-lying P(BTimR)-H LUMO results in minimal electron transport on exposure to ambient. Copolymer P3 exhibits a hole mobility approaching 0.1 cm(2) V(-1) s(-1) in top-gate OFETs, comparable to or slightly lower than current state-of-the-art p-type polymer semiconductors (0.1-0.6 cm(2) V(-1) s(-1)). Although BTI building

  开发具有良好加工性和优异器件环境稳定性的新型高迁移率聚合物半导体对于有机电子产品至关重要。我们报告了用于有机场效应晶体管 (OFET) 的一系列新的基于联噻吩酰亚胺 (BTI) 的聚合物的合成、表征、操纵电荷载流子极性和器件空气稳定性。通过增加供体共聚单体单元的共轭长度，从单噻吩 (P1) 到联噻吩 (P2) 再到四噻吩 (P3)，电子传输能力降低，而空穴传输能力增加。与电子迁移率为 10(-2) cm(2) V(-1) s(-1) 的 BTI 均聚物 P(BTimR) 相比，共聚物 P1 是双极性的，空穴和电子迁移率为 ~10(-4 ) 厘米(2) V(-1) s(-1), 而 P2 和 P3 的空穴迁移率分别为~10(-3) 和~10(-2) cm(2) V(-1) s(-1)。还研究了 P(BTimR) 均聚物 M(n) 对薄膜形态和器件性能的影响。高 M(n) 批次 P(BTimR)-H