5,5'''-bis-trimethylsilyl-3,3'''-bisperfluorohexyl-2,2':5',2'':5'',2'''-quaterthiophene | 790712-89-9

• 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: 5,5'''-bis-trimethylsilyl-3,3'''-bisperfluorohexyl-2,2':5',2'':5'',2'''-quaterthiophene
• 英文别名: 5,5'''-bistrimethylsilyl-3,3'''-diperfluorohexyl-2,2':5',2'':5'',2'''-quaterthiophene；Trimethyl-[4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)-5-[5-[5-[3-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)-5-trimethylsilylthiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]silane
• CAS: 790712-89-9
• 化学式: C₃₄H₂₄F₂₆S₄Si₂
• 分子量: 1110.96
• InChiKey: DIWUQODYMIVCBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.41
• 重原子数：
  66
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  5,5'''-bis-trimethylsilyl-3,3'''-bisperfluorohexyl-2,2':5',2'':5'',2'''-quaterthiophene 在 溴 作用下， 以 氯仿 为溶剂， 以79.5%的产率得到5,5'''-dibromo-3,3'''-diperfluorohexyl-2,2':5',2'':5'',2'''-quaterthiophene
  参考文献：
  名称：

  Building Blocks for n-Type Molecular and Polymeric Electronics. Perfluoroalkyl- versus Alkyl-Functionalized Oligothiophenes (nT; n = 2−6). Systematics of Thin Film Microstructure, Semiconductor Performance, and Modeling of Majority Charge Injection in Field-Effect Transistors

  摘要：

  The solid-state properties and FET electrical behavior of several series of alpha,omega- and beta,beta'-fluorocarbon- and alkyl-substituted and unsubstituted oligothiophenes nTs (n = 2-6) are compared and contrasted. The thin films were grown by slow vacuum deposition over a range of substrate temperatures and/or by casting from solution and were investigated by X-ray diffraction and scanning electron microscopy. Our results indicate that vacuum deposition at 60-80 degreesC affords films with remarkably similar microstructures despite the extensive H --> F substitution. Trends in observed d spacing versus molecular core extension provide quantitative information on molecular orientation. Field-effect transistor measurements performed for all systems and having the same device structure, components, and fabrication conditions demonstrate that all nTs functionalized with fluorocarbon chains at the thiophene termini are n-type semiconductors, in contrast to the p-type activity of the remaining systems. One of these systems, alpha,omega,-diperfluorohexyl-4T, exhibits a mobility of 0.22 cm(2)/(V s) and an I-on:I-off ratio of 10(6), one of the highest so far reported for an n-type organic semiconductor. The effect of substitution regiochemistry on FET majority charge carrier was additionally studied, in the case of a 6T core, by shifting the fluorocarbon substituents from the terminal to the central thiophene units. Finally, we propose a simple theoretical model for electrode/organic interfacial carrier injection. The results suggest why modest substituent-induced changes in the injection barrier can produce working n-type materials.

  DOI：

  10.1021/ja0489846
• 作为产物：
  描述：

  3-bromo-2,2'-bithiophene 在 正丁基锂 、 铜 、 copper dichloride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 20.67h， 生成 5,5'''-bis-trimethylsilyl-3,3'''-bisperfluorohexyl-2,2':5',2'':5'',2'''-quaterthiophene
  参考文献：
  名称：

  N 型分子和聚合物电子的构建模块。全氟烷基-与烷基-功能化的低聚噻吩（nTs；n= 2-6）。系统合成、光谱学、电化学和固态组织

  摘要：

  描述了在取代基性质和连接、区域化学和低聚噻吩核心长度 (n) 方面不同的五个低聚噻吩 (nT) 系列的合成、比较物理化学性质和固态结构。这五个系列包括以下 25 种化合物：(i) alpha,omega-diperfluorohexyl-nTs 1 (DFH-nTs, n = 2-6), (ii) beta,beta'-diperfluorohexyl-nTs 2 (isoDFH-nTs, n = 2-6), (iii) α,omega-二己基-nTs 3 (DH-nTs, n = 2-6), (iv) β,β'-二己基-nTs 4 (isoDH-nTs, n = 2- 6)，和 (v) 未取代的低聚噻吩 5（alphanTs，n = 2-6）。所有新化合物均通过元素分析、质谱和多核 NMR 光谱进行表征。为了定量地探讨和解决共轭核取代的化学和区域化学如何影响分子和固态特性，通过差示扫描量

  DOI：

  10.1021/ja048988a