5-全氟己基-5'-溴-2,2'-二噻吩 | 327630-35-3

• 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
• 中文名称: 5-全氟己基-5'-溴-2,2'-二噻吩
• 英文名称: 5-bromo-5'-(tridecafluorohexyl)-2,2'-bithiophene
• 英文别名: 5-Perfluorohexyl-5'-bromo-2,2'-dithiophene；2-bromo-5-[5-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)thiophen-2-yl]thiophene
• CAS: 327630-35-3
• 化学式: C₁₄H₄BrF₁₃S₂
• 分子量: 563.201
• InChiKey: VOBUCWYYRVENGT-UHFFFAOYSA-N

物化性质

• 熔点：
  50-55°C
• 沸点：
  334.2±42.0 °C(Predicted)
• 密度：
  1.756±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  5-全氟己基-5'-溴-2,2'-二噻吩 在 四(三苯基膦)钯 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 、 氯苯 为溶剂， 190.0 ℃ 、15.0 kPa 条件下， 反应 0.02h， 生成 5''-bromo-5-tridecafluorohexyl-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Rapid synthesis and fluorous-phase purification of α-perfluorohexyloligothiophenes

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2006.11.165
• 作为产物：
  描述：

  全氟己基碘烷 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.75h， 生成 5-全氟己基-5'-溴-2,2'-二噻吩
  参考文献：
  名称：

  Tuning the Semiconducting Properties of Sexithiophene byα,ω-Substitution—α,ω-Diperfluorohexylsexithiophene: The First n-Type Sexithiophene for Thin-Film Transistors

  摘要：

  DOI：

  10.1002/1521-3773(20001215)39:24<4547::aid-anie4547>3.0.co;2-j

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
• A new method of using supercritical carbon dioxide as a green solvent for synthesis and purification of 5,5‴-bis(tridecafluorohexyl)-2,2′:5′,2″:5″,2‴-quaterthiophene, which is one of n-type organic semiconducting materials
  作者：Ryuji Hirase、Koji Honda、Mari Ishihara、Hideki Yoshioka、Hirosato Monobe

  DOI：10.1016/j.tetlet.2017.12.071

  日期：2018.1

  We have investigated synthesis as well as purification of 5,5‴-bis(tridecafluorohexyl)-2,2′:5′,2″:5″,2‴-quaterthiophene (BFH-4 T, n-type organic semiconducting material) using supercritical carbon dioxide (scCO2) as a green solvent. BFH-4T was obtained in good selectivity and high yield by TDAE/PdCl2-catalyzed reductive coupling reaction of 5-bromo-5′-(tridecafluorohexyl)-2,2′-bithiophene in scCO2

  我们研究了5,5′-双（三氟铝己基）-2,2′：5′，2″：5″，2′-四噻吩（BFH-4 T，n型有机半导体材料）的合成及纯化使用超临界二氧化碳（scCO 2）作为绿色溶剂。BFH-4T通过TDAE在良好的选择性和高收率获得/的PdCl 2催化的5-溴-5'的还原偶合反应- （十三氟）-2,2'-二噻吩在SCCO 2。我们还通过将scCO 2传递到反应容器中而成功建立了反应混合物的纯化方法。产物为BFH-4T的黄色粉末，纯度大于99％，并且不包含Pd催化剂。
• 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。
• US7374702B2
  申请人：——

  公开号：US7374702B2

  公开（公告）日：2008-05-20
• US7842198B2
  申请人：——

  公开号：US7842198B2

  公开（公告）日：2010-11-30