2-(tri-n-butylstannyl)-5-(1-perfluorohexyl)thiophene | 790712-82-2

• 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: 2-(tri-n-butylstannyl)-5-(1-perfluorohexyl)thiophene
• 英文别名: 2-perfluorohexyl-5-tri-n-butylstannylthiophene；2-perfluorohexyl-5-(tributylstannyl)thiophene；2-perfluorohexyl-5-tributylstannylthiophene；2-tributylstannyl-5-perfluorohexylthiophene
• CAS: 790712-82-2
• 化学式: C₂₂H₂₉F₁₃SSn
• 分子量: 691.227
• InChiKey: VYLXDKNZHYVQQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.0
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2-(tri-n-butylstannyl)-5-(1-perfluorohexyl)thiophene 在 四(三苯基膦)钯 、 碘 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氯化碳 、 甲苯 为溶剂， 反应 14.0h， 生成 4,4,5,5,6,6-Hexafluoro-1-(5-iodo-thiophen-2-yl)-3-(5-tridecafluorohexyl-thiophen-2-yl)-5,6-dihydro-4H-cyclopenta[c]thiophene
  参考文献：
  名称：

  Electronegative Oligothiophenes Based on a Hexafluorocyclopentene-Annelated Thiophene Unit

  摘要：

  [GRAPHICS]The synthesis of hexafluorocyclopenta[c] thiophene and its based oligothiophenes is described. The effectiveness of a hexafluorocyclopentene unit to lower the LUMO level without disturbing the effective conjugation could be unambiguously clarified by spectroscopic measurements and X-ray analysis.

  DOI：

  10.1021/ol062238j
• 作为产物：
  描述：

  全氟己基碘烷 在 copper bronze 、 lithium diisopropyl amide 作用下， 以 正己烷 、 二甲基亚砜 为溶剂， 反应 7.0h， 生成 2-(tri-n-butylstannyl)-5-(1-perfluorohexyl)thiophene
  参考文献：
  名称：

  Synthesis of Perfluoroalkyl End-Functionalized Poly(3-hexylthiophene) and the Effect of Fluorinated End Groups on Solar Cell Performance

  摘要：

  A series of well-defined perfluoroalkyl end-functionalized poly(3-hexylthiophenes) (P3HT) were synthesized by Stifle coupling of stannylated 2-perfluoralkylthiophene with the bromine end of P3HT. The length of the perfluoroalkyl end group was varied from -C4F13 to -C8F17. These polymers were fully characterized and tested in bulk heterojunction solar cells with phenyl-C-61-butyric acid methyl ester (PCBM) as the acceptor. Performance of the solar cells was highest for the unmodified P3HT and decreased as the length of the perfluoroalkyl end increased. The most affected device parameters were the short-circuit current density (J(sc)) and series resistance, pointing to lower charge carrier mobility and poor morphology as the cause for the lower performance. While the morphology of blends did not significantly change with perfluoroalkyl end modification, analysis of blended films by energy-filtered transmission electron microscopy (EF-TEM) revealed wider P3HT domains, consistent with the perfluorinated end groups segregating to the edge or exterior of P3HT domains, causing two domains to join. This study demonstrates that the perfluoroalkyl end group can be detrimental to polymer solar cell device performance, and further work toward understanding the interface between the donor and acceptor phases is required to fully understand this effect.

  DOI：

  10.1021/ma301397p

文献信息

• Building Blocks for N-Type Molecular and Polymeric Electronics. Perfluoroalkyl- versus Alkyl-Functionalized Oligothiophenes (nTs; <i>n</i> = 2−6). Systematic Synthesis, Spectroscopy, Electrochemistry, and Solid-State Organization
  作者：Antonio Facchetti、Myung-Han Yoon、Charlotte L. Stern、Geoffrey R. Hutchison、Mark A. Ratner、Tobin J. Marks

  DOI：10.1021/ja048988a

  日期：2004.10.1

  The synthesis, comparative physicochemical properties, and solid-state structures of five oligothiophene (nT) series differing in substituent nature and attachment, regiochemistry, and oligothiophene core length (n) are described. These five series include the following 25 compounds: (i) alpha,omega-diperfluorohexyl-nTs 1 (DFH-nTs, n = 2-6), (ii) beta,beta'-diperfluorohexyl-nTs 2 (isoDFH-nTs, n = 2-6)

  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
• Electronegative Oligothiophenes for n-Type Semiconductors:  Difluoromethylene-Bridged Bithiophene and Its Oligomers
  作者：Yutaka Ie、Masashi Nitani、Motomi Ishikawa、Ken-ichi Nakayama、Hirokazu Tada、Takahiro Kaneda、Yoshio Aso

  DOI：10.1021/ol070584a

  日期：2007.5.1

  The synthesis of difluoromethylene-bridged bithiophene and its oligothiophenes are reported. The spectroscopic and electrochemical measurement as well as X-ray analyses unambiguously revealed that the difluoromethylene bridge largely contributes to keeping planarity between the thiophene rings and lowering the LUMO level. The perfluorohexyl-substituted quaterthiophene derivatives showed n-type semiconducting

  报道了二氟亚甲基桥联的联噻吩及其寡噻吩的合成。光谱和电化学测量以及X射线分析明确表明，二氟亚甲基桥在很大程度上有助于保持噻吩环之间的平面性并降低LUMO含量。全氟己基取代的四噻吩衍生物表现出n型半导体行为，场效应电子迁移率高达0.018 cm2 V-1 s-1。
• [EN] ORGANIC SEMICONDUCTOR MATERIAL<br/>[FR] MATÉRIAU SEMI-CONDUCTEUR ORGANIQUE
  申请人：E T C SRL

  公开号：WO2014076650A1

  公开（公告）日：2014-05-22

  The present invention relates to novel compounds useful as organic semiconductor materials, and semiconductor devices containing said organic semiconductor materials.

  本发明涉及一种新型化合物，可用作有机半导体材料，以及含有所述有机半导体材料的半导体器件。
• Molecular Tailoring of New Thieno(bis)imide-Based Semiconductors for Single Layer Ambipolar Light Emitting Transistors
  作者：Manuela Melucci、Laura Favaretto、Massimo Zambianchi、Margherita Durso、Massimo Gazzano、Alberto Zanelli、Magda Monari、Maria G. Lobello、Filippo De Angelis、Viviana Biondo、Gianluca Generali、Stefano Troisi、Wouter Koopman、Stefano Toffanin、Raffaella Capelli、Michele Muccini

  DOI：10.1021/cm303224a

  日期：2013.3.12

  Organic molecular semiconductors are key components for a new generation of low cost, flexible, and large area electronic devices. In particular, ambipolar semiconductors endowed with electroluminescent properties have the potential to enable a photonic field-effect technology platform, whose key building blocks are the emerging organic light-emitting transistor (OLET) devices. To this aim, the design

  有机分子半导体是新一代低成本，柔性和大面积电子设备的关键组件。特别是，具有电致发光特性的双极性半导体具有实现光子场效应技术平台的潜力，该平台的关键构件是新兴的有机发光晶体管（OLET）器件。为了这个目的，非常需要结合固态的有效电学和光学特性的创新分子构型的设计。在这里，我们研究了在高性能单极低聚噻吩半导体中，噻吩（双）酰亚胺（TBI）部分作为端基的插入对所得材料的包装，电学和光电性能的影响。我们证明，不管HOMO-LUMO能量如何，轨道分布，和分子堆积图样，TBI末端部分将单极性和非发射性的低聚噻吩半导体转换为双极性和电致发光材料。值得注意的是，新开发的材料使得单层分子双极性OLET的制造具有与等效聚合物单层器件相当的光功率。
• EP1997821
  申请人：——

  公开号：——

  公开（公告）日：——