1,2-bis(5-trimethylstannylthiophen-2-yl)ethane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 1,2-bis(5-trimethylstannylthiophen-2-yl)ethane
• 英文别名: 1,2-Bis(5-(trimethylstannyl)thiophen-2-yl)ethane；trimethyl-[5-[2-(5-trimethylstannylthiophen-2-yl)ethyl]thiophen-2-yl]stannane
• 化学式: C₁₆H₂₆S₂Sn₂
• 分子量: 519.934
• InChiKey: WCHYSNDRWAMSCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  噻吩偶姻 在 正丁基锂 、 一水合肼 作用下， 以 四氢呋喃 、 乙二醇 为溶剂， 生成 1,2-bis(5-trimethylstannylthiophen-2-yl)ethane
  参考文献：
  名称：

  Complementary Semiconducting Polymer Blends: The Influence of Conjugation-Break Spacer Length in Matrix Polymers

  摘要：

  The concept of complementary semiconducting polymer blends (c-SPBs) for efficient charge transport was recently proposed and established by our group. In this study, we aim to reveal the influence of the length of conjugation-break spacers (CBSs) on charge transport properties of the matrix polymers and their corresponding complementary polymer blends. A series of 11 DPP-based semiconducting polymers DPP-Cm (m = 2-12) that incorporate CBSs of 2-12 methylene units along the polymer backbones were prepared and characterized. The UV vis spectra and the ultraviolet photoelectron spectroscopy (UPS) measurements show that the CBS length has marginal influence on the polymer absorption spectra, energy levels, and band gaps. It also has little impact on polymer decomposition temperatures. However, the CBS length has a profound influence on polymer phase transition and the heat of fusion. As for the melt transitions, an odd even effect is observed from DPP-C2 to DPP-C7, in which polymers with even-numbered CBSs show higher melting points than their adjacent odd-numbered derivatives. The trend is opposite for heat of fusion. The polymers with odd-numbered CBSs exhibit larger heat of fusion, indicating higher ordering and crystallinity. The odd even effect is also found in surface morphologies of the polymers by atomic force microscopy (AFM). The polymers with the even CBSs have a more interconnected feature that appear more fibrillar than the polymers with the odd linkages. As far as charge carrier mobility is concerned, the average number drops from 0.023 cm2 V-1 s(-1) to 7.9 X 10(-6) cm(2) V-1 s(-1) as the CBS moves from C2 to C12. It is intriguing to observe that even-numbered polymers outperform the adjacent odd-numbered polymers, despite the fact that the latter show higher ordering and crystallinity in thin films. When these polymers are mixed with fully conjugated DPP-CO (2 wt %, designated as tie chain polymer), the obtained cSPBs witness a dramatic increase (2-4 orders of magnitude) in charge carrier mobility. Interestingly, the odd even effect is not found for charge transport in the c-SPBs. This work reveals that the length of CBSs plays a significant role in charge transport properties of the matrix polymers and reconfirms that efficient charge transport properties of the c-SPB result from the interactions between matrix polymers and tie chain polymers. This begins to provide guidelines as to what spacer lengths may be utilized to offer the best balance between processing and charge transport properties.

  DOI：

  10.1021/acs.macromol.6b00050

文献信息

• Heavily n-Dopable π-Conjugated Redox Polymers with Ultrafast Energy Storage Capability
  作者：Yanliang Liang、Zhihua Chen、Yan Jing、Yaoguang Rong、Antonio Facchetti、Yan Yao

  DOI：10.1021/jacs.5b02290

  日期：2015.4.22

  We report here the first successful demonstration of a pi-conjugated redox polymer simultaneously featuring a pi-conjugated backbone and integrated redox sites, which can be stably and reversibly n-doped to a high doping level of 2.0 with significantly enhanced electronic conductivity. The properties of such a heavily n-dopable polymer, poly[N,N'-bis(2-octyldodecyl)-1,4,5,8-naphthalenedicarboximide-2,6-diyl]-alt-5,5'-(2,2'-bithiophene)} (P(NDI2OD-T2)), were compared vis-a-vis to those of the corresponding backbone-insulated poly[N,N'-bis(2-octyldodecyl)-1,4,5,8-naphthalenedicarboximide-2,6-diyl]-alt-5,5'-[2,2'-(1,2-ethanediyl)bithiophene]} (P(NDI2OD-TET)). When evaluated as a charge storage material for rechargeable Li batteries, P(NDI2OD-T2) delivers 95% of its theoretical capacity at a high rate of 100C (72 s per charge-discharge cycle) under practical measurement conditions as well as 96% capacity retention after 3000 cycles of deep discharge-charge. Electrochemical, impedance, and charge-transport measurements unambiguously demonstrate that the ultrafast electrode kinetics of P(NDI2OD-T2) are attributed to the high electronic conductivity of the polymer in the heavily n-doped state.
• Complementary Semiconducting Polymer Blends: The Influence of Conjugation-Break Spacer Length in Matrix Polymers
  作者：Xikang Zhao、Yan Zhao、Qu Ge、Kamal Butrouna、Ying Diao、Kenneth R. Graham、Jianguo Mei

  DOI：10.1021/acs.macromol.6b00050

  日期：2016.4.12

  The concept of complementary semiconducting polymer blends (c-SPBs) for efficient charge transport was recently proposed and established by our group. In this study, we aim to reveal the influence of the length of conjugation-break spacers (CBSs) on charge transport properties of the matrix polymers and their corresponding complementary polymer blends. A series of 11 DPP-based semiconducting polymers DPP-Cm (m = 2-12) that incorporate CBSs of 2-12 methylene units along the polymer backbones were prepared and characterized. The UV vis spectra and the ultraviolet photoelectron spectroscopy (UPS) measurements show that the CBS length has marginal influence on the polymer absorption spectra, energy levels, and band gaps. It also has little impact on polymer decomposition temperatures. However, the CBS length has a profound influence on polymer phase transition and the heat of fusion. As for the melt transitions, an odd even effect is observed from DPP-C2 to DPP-C7, in which polymers with even-numbered CBSs show higher melting points than their adjacent odd-numbered derivatives. The trend is opposite for heat of fusion. The polymers with odd-numbered CBSs exhibit larger heat of fusion, indicating higher ordering and crystallinity. The odd even effect is also found in surface morphologies of the polymers by atomic force microscopy (AFM). The polymers with the even CBSs have a more interconnected feature that appear more fibrillar than the polymers with the odd linkages. As far as charge carrier mobility is concerned, the average number drops from 0.023 cm2 V-1 s(-1) to 7.9 X 10(-6) cm(2) V-1 s(-1) as the CBS moves from C2 to C12. It is intriguing to observe that even-numbered polymers outperform the adjacent odd-numbered polymers, despite the fact that the latter show higher ordering and crystallinity in thin films. When these polymers are mixed with fully conjugated DPP-CO (2 wt %, designated as tie chain polymer), the obtained cSPBs witness a dramatic increase (2-4 orders of magnitude) in charge carrier mobility. Interestingly, the odd even effect is not found for charge transport in the c-SPBs. This work reveals that the length of CBSs plays a significant role in charge transport properties of the matrix polymers and reconfirms that efficient charge transport properties of the c-SPB result from the interactions between matrix polymers and tie chain polymers. This begins to provide guidelines as to what spacer lengths may be utilized to offer the best balance between processing and charge transport properties.