3-bromo-4-hexyl-2,5-bis(trimethylsilyl)thiophene | 488127-59-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3-bromo-4-hexyl-2,5-bis(trimethylsilyl)thiophene
• 英文别名: (3-Bromo-4-hexyl-5-trimethylsilylthiophen-2-yl)-trimethylsilane；(3-bromo-4-hexyl-5-trimethylsilylthiophen-2-yl)-trimethylsilane
• CAS: 488127-59-9
• 化学式: C₁₆H₃₁BrSSi₂
• 分子量: 391.563
• InChiKey: IKWCUNDQJLCKNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  3-bromo-4-hexyl-2,5-bis(trimethylsilyl)thiophene 在 正丁基锂 、 溴 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 2,5-dibromo-3-fluoro-4-hexylthiophene
  参考文献：
  名称：

  Influence of Backbone Fluorination in Regioregular Poly(3-alkyl-4-fluoro)thiophenes

  摘要：

  We report two strategies toward the synthesis of 3-alkyl-4-fluorothiophenes containing straight (hexyl and octyl) and branched (2-ethylitexyl) alkyl groups. We demonstrate that treatment of the dibrominated monomer with 1 equiv of alkyl Grignard reagent leads to the formation, of a single regioisomer as:a result of the pronounced directing effect of the fluor-hie group. Polymerization of the resulting species affords highly regioregular poly(3-alkyl-4-fluoro)-thiophenes. Comparison Of their properties to those of the analogous non-fluorinated polymers shows that backbone fluorination leads to an increase in the polymer ionization potential without a significant change in optical band gap. Fluorination also results in an enhanced tendency to aggregate in solution, which is ascribed to a more co-planar backbone on the basis of Raman and DFT calculations. Average charge carrier mobilities in field-effect transistors are found to increase by up to a factor of 5 for the fluorinated polymers.

  DOI：

  10.1021/jacs.5b02785
• 作为产物：
  描述：

  3-己基噻吩 在 正丁基锂 、 溴 、 溶剂黄146 作用下， 生成 3-bromo-4-hexyl-2,5-bis(trimethylsilyl)thiophene
  参考文献：
  名称：

  一种基于3氟4己基噻吩的宽带隙供体聚合物，可实现10.9％效率的生态友好型非富勒烯有机太阳能电池

  摘要：

  非富勒烯有机太阳能电池（NFOSC）由于使用低成本卷对卷技术可用于柔性轻量产品，因此吸引了越来越多的学术和工业兴趣。在这项工作中，使用苯并二噻吩（BDT）衍生物设计和合成了两种宽带隙（WBG）聚合物，即P（fTh-BDT）-C6和P（fTh-2DBDT）-C6。通过将氟和烷基链同时引入一个噻吩（Th）单元，可以实现良好的氧化稳定性和高溶解度。固态P（fTh-2DBDT）-C6膜具有WBG光学吸收，合适的边界轨道能级和强大的π-π堆积效应。此外，P（fTh-2DBDT）-C6在卤代和非卤代溶剂中均显示出良好的溶解性，表明其适合作为NFOSC的供体聚合物。P（fTh-2DBDT）-C6：3,9-bis（2-亚甲基-（3-（1，1-二氰基亚甲基）-茚满酮））-5,5,11,11-四（5-己基噻吩基）-二硫代[2,3-d：2′，3′-d']-s-茚满[1,2-使用氯苯/ 1,8-二碘辛烷（CB /

  DOI：

  10.1002/smll.201805321

文献信息

• 3-Fluoro-4-hexylthiophene as a Building Block for Tuning the Electronic Properties of Conjugated Polythiophenes
  作者：Frédéric Gohier、Pierre Frère、Jean Roncali

  DOI：10.1021/jo302571u

  日期：2013.2.15

  3-Fluoro-4-hexylthiophene has been prepared by a synthetic route involving perbromination of 3-hexylthiophene followed by protection of the 2- and 5-positions of thiophene by trimethylsilyl groups and bromine/fluorine exchange. As expected, 3-hexyl-4-fluorothiophene oxidizes at a higher potential than 3-hexylthiophene; however, all attempts to electropolymerize this new thiophenic monomer have remained unsuccessful. Three terthienyls containing 3-hexylthiophene, 3-fluoro-4-hexylthiophene, and 3-bromo-4-hexylthiophene as the median group have been synthesized and used as substrates for electropolymerization. The electronic properties of the starting terthienyls and the resulting polymers have been analyzed by cyclic voltammetry and UV-vis spectroscopy, and the effects of substitution of the median thiophene ring are discussed.
• Influence of Backbone Fluorination in Regioregular Poly(3-alkyl-4-fluoro)thiophenes
  作者：Zhuping Fei、Pierre Boufflet、Sebastian Wood、Jessica Wade、John Moriarty、Eliot Gann、Erin L. Ratcliff、Christopher R. McNeill、Henning Sirringhaus、Ji-Seon Kim、Martin Heeney

  DOI：10.1021/jacs.5b02785

  日期：2015.6.3

  We report two strategies toward the synthesis of 3-alkyl-4-fluorothiophenes containing straight (hexyl and octyl) and branched (2-ethylitexyl) alkyl groups. We demonstrate that treatment of the dibrominated monomer with 1 equiv of alkyl Grignard reagent leads to the formation, of a single regioisomer as:a result of the pronounced directing effect of the fluor-hie group. Polymerization of the resulting species affords highly regioregular poly(3-alkyl-4-fluoro)-thiophenes. Comparison Of their properties to those of the analogous non-fluorinated polymers shows that backbone fluorination leads to an increase in the polymer ionization potential without a significant change in optical band gap. Fluorination also results in an enhanced tendency to aggregate in solution, which is ascribed to a more co-planar backbone on the basis of Raman and DFT calculations. Average charge carrier mobilities in field-effect transistors are found to increase by up to a factor of 5 for the fluorinated polymers.
• A 3-Fluoro-4-hexylthiophene-Based Wide Bandgap Donor Polymer for 10.9% Efficiency Eco-Friendly Nonfullerene Organic Solar Cells
  作者：Jeong Eun Yu、Sung Jae Jeon、Jun Young Choi、Yong Woon Han、Eui Jin Ko、Doo Kyung Moon

  DOI：10.1002/smll.201805321

  日期：2019.3

  Nonfullerene organic solar cells (NFOSCs) are attracting increasing academic and industrial interest due to their potential uses for flexible and lightweight products using low‐cost roll‐to‐roll technology. In this work, two wide bandgap (WBG) polymers, namely P(fTh‐BDT)‐C6 and P(fTh‐2DBDT)‐C6, are designed and synthesized using benzodithiophene (BDT) derivatives. Good oxidation stability and high

  非富勒烯有机太阳能电池（NFOSC）由于使用低成本卷对卷技术可用于柔性轻量产品，因此吸引了越来越多的学术和工业兴趣。在这项工作中，使用苯并二噻吩（BDT）衍生物设计和合成了两种宽带隙（WBG）聚合物，即P（fTh-BDT）-C6和P（fTh-2DBDT）-C6。通过将氟和烷基链同时引入一个噻吩（Th）单元，可以实现良好的氧化稳定性和高溶解度。固态P（fTh-2DBDT）-C6膜具有WBG光学吸收，合适的边界轨道能级和强大的π-π堆积效应。此外，P（fTh-2DBDT）-C6在卤代和非卤代溶剂中均显示出良好的溶解性，表明其适合作为NFOSC的供体聚合物。P（fTh-2DBDT）-C6：3,9-bis（2-亚甲基-（3-（1，1-二氰基亚甲基）-茚满酮））-5,5,11,11-四（5-己基噻吩基）-二硫代[2,3-d：2′，3′-d']-s-茚满[1,2-使用氯苯/ 1,8-二碘辛烷（CB /