5-perfluorohexyl-2,2':5',2''-terthiophene | 790712-83-3

• 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-perfluorohexyl-2,2':5',2''-terthiophene
• 英文别名: 5-tridecafluorohexyl-2,2':5',2''-terthiophene；5-(Tridecafluorohexyl)-2,2':5',2''-terthiophene；2-thiophen-2-yl-5-[5-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)thiophen-2-yl]thiophene
• CAS: 790712-83-3
• 化学式: C₁₈H₇F₁₃S₃
• 分子量: 566.431
• InChiKey: RPDFIUBCBNVIIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  5-perfluorohexyl-2,2':5',2''-terthiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以68%的产率得到5''-bromo-5-tridecafluorohexyl-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Non-symmetrical oligothiophenes with ‘incompatible’ substituents

  摘要：

  The syntheses of oligothiophenes 1 and 2 comprising two different types of peripheral substituents, namely alkyl and perfluoroalkyl, is reported. The key synthetic step is the Pd-catalyzed cross-coupling of perfluoroalkylated bromide 3 with an appropriate boronate. This molecular design is expected to promote unusual two-layer packing, which is of interest for application in electronic devices. Quaterthiophene 1 forms smectic mesophase, though in the narrow temperature range, and is suitable for the fabrication of thin films by solution processing methods. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.029
• 作为产物：
  描述：

  alpha-三联噻吩 在 N-溴代丁二酰亚胺(NBS) 、 铜 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 5-perfluorohexyl-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Non-symmetrical oligothiophenes with ‘incompatible’ substituents

  摘要：

  The syntheses of oligothiophenes 1 and 2 comprising two different types of peripheral substituents, namely alkyl and perfluoroalkyl, is reported. The key synthetic step is the Pd-catalyzed cross-coupling of perfluoroalkylated bromide 3 with an appropriate boronate. This molecular design is expected to promote unusual two-layer packing, which is of interest for application in electronic devices. Quaterthiophene 1 forms smectic mesophase, though in the narrow temperature range, and is suitable for the fabrication of thin films by solution processing methods. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.029

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
• n-Type Thiophene Semiconductors
  申请人：Marks Tobin J.

  公开号：US20080293937A1

  公开（公告）日：2008-11-27

  The new fluorocarbon-functionalized and/or heterocycle-modified polythiophenes, in particular, α,ω-diperfluorohexylsexithiophene DFH-6T can be straightforwardly prepared in high yield and purity. Introduction of such modifications to a thiophene core affords enhanced thermal stability and volatility, and increased electron affinity versus the unmodified compositions of the prior art. Evaporated films behave as n-type semiconductors, and can be used to fabricate thin film transistors with FET mobilities ˜0.01 cm 2 /Vs—some of the highest reported to date for n-type organic semiconductors.

  新的氟碳功能化和/或杂环改性的聚噻吩，特别是α,ω-双氟己基六噻吩DFH-6T可以直接高产率和纯度制备。将这些修饰引入到噻吩核心可以提高热稳定性和挥发性，增加电子亲和力，相比先前艺术中未经修改的组分。蒸发膜表现为n型半导体，可用于制备具有FET迁移率˜0.01 cm2/Vs的薄膜晶体管-这是迄今为止报道的n型有机半导体中最高的一些值。
• n-Type thiophene semiconductors
  申请人：Marks J. Tobin

  公开号：US20050119440A1

  公开（公告）日：2005-06-02

  The new fluorocarbon-functionalized and/or heterocycle-modified polythiophenes, in particular, α,ω-diperfluorohexylsexithiophene DFH-6T can be straightforwardly prepared in high yield and purity. Introduction of such modifications to a thiophene core affords enhanced thermal stability and volatility, and increased electron affinity versus the unmodified compositions of the prior art. Evaporated films behave as n-type semiconductors, and can be used to fabricate thin film transistors with FET mobilities ˜0.01 cm 2 /Vs—some of the highest reported to date for n-type organic semiconductors.

  新的氟碳功能化和/或杂环修饰的聚噻吩，尤其是α，ω-二氟己基六噻吩DFH-6T可以直接制备高收率和高纯度。将这样的修饰引入到噻吩核心中可提供比先前未经修改的组合物具有增强的热稳定性和挥发性，以及增加的电子亲和力。蒸发薄膜表现为n型半导体，并可用于制备具有FET迁移率约0.01 cm2/Vs的薄膜晶体管-这是迄今为止报道的n型有机半导体中最高的之一。
• n-type thiophene semiconductors
  申请人：Northwestern University

  公开号：US20030080324A1

  公开（公告）日：2003-05-01

  The new fluorocarbon-functionalized and/or heterocycle-modified polythiophenes, in particular, &agr;,&ohgr;-diperfluorohexylsexithiophene DFH-6T can be straightforwardly prepared in high yield and purity. Introduction of such modifications to a thiophene core affords enhanced thermal stability and volatility, and increased electron affinity versus the unmodified compositions of the prior art. Evaporated films behave as n-type semiconductors, and can be used to fabricate thin film transistors with FET mobilities 0.01 cm 2 /Vs—some of the highest reported to date for n-type organic semiconductors. 1

  新的氟碳功能化和/或杂环改性的聚噻吩，尤其是α，ω-二氟己基六噻吩DFH-6T可以直接高产高纯度制备。将这种改性引入到噻吩核心中，可提高热稳定性和挥发性，并增加电子亲和力，相比于先前的未改性组合物。蒸发膜表现为n型半导体，可用于制备薄膜晶体管，其场效应迁移率为0.01 cm2/Vs，是迄今为止报道的n型有机半导体中最高的之一。1
• Rapid synthesis and fluorous-phase purification of α-perfluorohexyloligothiophenes
  作者：Mark C. McCairn、Michael L. Turner

  DOI：10.1016/j.tetlet.2006.11.165

  日期：2007.2

  A high-throughput methodology that facilitates the synthesis, purification and characterisation of pi-conjugated oligothiophenes has been developed. alpha-Perfluorohexyltetrathiophene was synthesised by sequential alpha-bromination and microwave promoted Stille cross-coupling reactions. Each synthetic transformation was followed by a fluorous solid-phase extraction (F-SPE) procedure to isolate the desired alpha-perfluorohexyloligothiophene. After a single F-SPE, each oligomer gave essentially one peak by GC-MS, which enabled stepwise growth of a tetrathiophene with no additional purification of the intermediate building blocks required. We anticipate that microwave accelerated synthesis in conjunction with fluorous-phase purification of pi-conjugated systems will find generic application in the high-throughput parallel-synthesis of novel organic materials for semiconductor applications. (c) 2006 Elsevier Ltd. All rights reserved.