(3-十二烷基-2-噻吩基)三甲基锡烷 | 1186317-24-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 金属芳基
• 中文名称: (3-十二烷基-2-噻吩基)三甲基锡烷
• 英文名称: (3-dodecylthiophen-2-yl)trimethylstannane
• 英文别名: (3-Dodecyl-2-thienyl)trimethylstannane；(3-dodecylthiophen-2-yl)-trimethylstannane
• CAS: 1186317-24-7
• 化学式: C₁₉H₃₆SSn
• 分子量: 415.271
• InChiKey: WCHNLGXGBIUEAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.76
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  4,7-二溴-2,1,3-苯并噻二唑 、 (3-十二烷基-2-噻吩基)三甲基锡烷 在 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以65%的产率得到4,7-bis(3-dodecyl-2-thienyl)-2,1,3-benzothiadiazole
  参考文献：
  名称：

  Thiophene–benzothiadiazole–thiophene (D–A–D) based polymers: effect of donor/acceptor moieties adjacent to D–A–D segment on photophysical and photovoltaic properties

  摘要：

  基于噻吩（供体）和苯并噻二唑（受体）单元的新型推拉共聚物--聚[4,7-双（3-十二烷基噻吩-2-基）苯并噻二唑-共噻吩]（PT3B1）和聚[4、7-双(3-十二烷基噻吩-2-基)苯并噻二唑-共噻吩]（PT2B2）。凝胶渗透色谱法显示，这两种聚合物的平均分子量分别为 31â100 和 8400 g molâ1 。这两种聚合物在 300 至 650 纳米的紫外可见光范围内均有吸收。与这两种共聚物的溶液相比，薄膜的吸收边缘出现了明显的红移；光带隙在 1.7 至 1.8 eV 之间。循环伏安法显示了可逆的氧化和还原过程，计算得出的 HOMO 能级在 5.2 至 5.4 eV 之间。在对这两种材料进行有机场效应晶体管（OFET）测试时，PT3B1 显示出 6.1 Ã 10â4 cm2 Vâ1 sâ1 的空穴迁移率，而 PT2B2 则没有显示出任何场效应传输。这两种共聚物与作为电子受体的甲烷富勒烯结合后，都显示出光电效应。当共聚物PT3B1与[70]PCBM以1â:â4的比例混合时，性能最佳，在模拟空气质量（AM）1.5全球（1.5 G）照明条件（100 mW cmâ2）下，短路电流为7.27 mA cmâ2，开路电压为0.85 V，填充因子为41%，功率转换效率为2.54%。利用 PT2B2 代替 PT3B1 的类似器件性能有所下降，短路电流为 4.8 mA cmâ2，开路电压为 0.73 V，填充因子为 30%，功率转换效率约为 1.06%。

  DOI：

  10.1039/c1jm10649j
• 作为产物：
  描述：

  三甲基氯化锡 、 3-十二烷基噻吩 在 C₄H₉Li 作用下， 以 四氢呋喃 为溶剂， 生成 (3-十二烷基-2-噻吩基)三甲基锡烷
  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

• New Form of an Old Natural Dye: Bay-Annulated Indigo (BAI) as an Excellent Electron Accepting Unit for High Performance Organic Semiconductors
  作者：Bo He、Andrew B. Pun、Danylo Zherebetskyy、Yao Liu、Feng Liu、Liana M. Klivansky、Alexandra M. McGough、Benjamin A. Zhang、Kelvin Lo、Thomas P. Russell、Linwang Wang、Yi Liu

  DOI：10.1021/ja508807m

  日期：2014.10.22

  electron acceptor was synthesized from one-step functionalization of the readily available indigo dye. The resulting bay-annulated indigo (BAI) was utilized for the preparation of a series of novel donor-acceptor small molecules and polymers. As revealed experimentally and by theoretical calculations, substituted BAIs have stronger electron accepting characteristics when compared to several premier electron

  从容易获得的靛蓝染料的一步官能化合成了一种新型电子受体。所得海湾环化靛蓝 (BAI) 用于制备一系列新型供体-受体小分子和聚合物。正如实验和理论计算所揭示的那样，与几种主要的缺电子结构单元相比，取代的 BAI 具有更强的电子接受特性。因此，包含 BAI 受体的供体-受体材料具有低的 LUMO 能级和小的 HOMO-LUMO 间隙。BAI 供体-受体聚合物薄膜的原位掠入射广角 X 射线散射研究表明热处理后结晶度提高。基于这些聚合物的场效应晶体管显示出优异的双极传输行为，
• Bay-annulated indigo (BAI) as an excellent electron accepting building block for high performance organic semiconductors
  申请人：Liu Yi

  公开号：US09196846B2

  公开（公告）日：2015-11-24

  A novel electron acceptor based on bay-annulated indigo (BAI) was synthesized and used for the preparation of a series of high performance donor-acceptor small molecules and polymers. The resulting materials possess low-lying LUMO energy level and small HOMO-LUMO gaps, while their films exhibited high crystallinity upon thermal treatment, commensurate with high field effect mobilities and ambipolar transfer characteristics.

  基于湾环化靛蓝（BAI）的新型电子受体已合成，并用于制备一系列高性能的供体-受体小分子和聚合物。所得材料具有较低的LUMO能级和较小的HOMO-LUMO间隙，其薄膜在热处理后表现出高结晶性，与高场效应迁移率和双极传输特性相称。
• Fine Structural Tuning of Cyanated Dithieno[3,2-<i>b</i>:2′,3′-<i>d</i>]silole–Oligothiophene Copolymers: Synthesis, Characterization, and Photovoltaic Response
  作者：Mirko Seri、Margherita Bolognesi、Zhihua Chen、Shaofeng Lu、Wouter Koopman、Antonio Facchetti、Michele Muccini

  DOI：10.1021/ma4011186

  日期：2013.8.27

  We report here the synthesis and characterization of a new series of semiconducting polymers based on dithieno[3,2-b:2′,3′-d]silole (SiDT) copolymerized with cyanated oligothiophenes (-2T- or -4T-) units. The effect of the fine structural tuning of the thiophene-based spacer on optical, electronic, morphological, and photophysical properties of the resulting polymers is investigated and correlated

  我们在这里报告了一系列新的半导体聚合物的基于噻吩并合成和表征[3,2- b：2'，3'- d ]噻咯（SIDT）与氰化低聚噻吩共聚（-2T-或-4T-）单元。对所得到的聚合物的光学，电子，形态学，和光物理性质的基于噻吩的间隔物的结构细调谐的效果进行了研究，并与有机光伏（OPV）性能相关。使用此类共聚物作为电子供体材料的体异质结（BHJ）太阳能电池被制造，优化和充分表征。作为合理的结构修饰结果，〜5％的PCE和开路电压（V OC）大于0.8 V的，而不需要额外的热退火来实现。
• 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.