5-全氟己基-2,2′-联噻吩 | 327630-34-2

• 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-2,2′-联噻吩
• 英文名称: 5-Perfluorohexyl-2,2'-dithiophene
• 英文别名: 5-Perfluorohexyl-2,2'-bithiophene；2-thiophen-2-yl-5-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)thiophene
• CAS: 327630-34-2
• 化学式: C₁₄H₅F₁₃S₂
• 分子量: 484.305
• InChiKey: KILCWELZTSEPSB-UHFFFAOYSA-N

物化性质

• 熔点：
  50-55°C
• 沸点：
  304.6±42.0 °C(Predicted)
• 密度：
  1.590±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  29
• 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

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  5-全氟己基-2,2′-联噻吩 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 为溶剂， 反应 7.0h， 生成 α,ω-Diperfluorohexylsexithiophene
  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
• 作为产物：
  描述：

  全氟己基碘烷 、 5-溴-2,2-双噻吩 在 铜 作用下， 生成 5-全氟己基-2,2′-联噻吩
  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

文献信息

• 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。
• Effect of electron-withdrawing groups on molecular properties of naphthyl and anthryl bithiophenes as potential n-type semiconductors
  作者：Lucia Feriancová、Marek Cigáň、Katarína Gmucová、Jozef Kožíšek、Vojtech Nádaždy、Martin Putala

  DOI：10.1039/d1nj01100f

  日期：——

  2-naphthyl and 2-anthrylbithiophene derivatives with electron acceptor groups were synthesised using the Negishi or Suzuki cross-coupling reaction as a key step. We present a comparison of theoretical and experimental values of the LUMO and gap energies of these derivatives and the effect of the various electron-withdrawing groups on their optical and electrochemical properties. DFT-calculated frontier

  使用Negishi或Suzuki交叉偶联反应作为关键步骤，合成了十个带有电子受体基团的十个2-萘基和2-蒽基联噻吩衍生物。我们比较了这些衍生物的LUMO和间隙能的理论和实验值，以及各种吸电子基团对其光学和电化学性质的影响。DFT计算的边界轨道能量差已显示出遵循实验确定的值的趋势。吸电子基团在π-共轭中的参与降低了LUMO能级，并且以两个系列中的全氟烷基，酰基，全氟酰基，硝基硝基二氰基乙烯基的顺序缩小了能隙。TD-DFT计算可以更好地理解电子跃迁。联噻吩的s-trans与s-cis构象）。
• Synthesis by MW-assisted direct arylation, side-arms driven self-assembly and functional properties of 9,10-dithienylanthracene orthogonal materials
  作者：Margherita Durso、Massimo Zambianchi、Alberto Zanelli、M. Grazia LoBello、Filippo De Angelis、Stefano Toffanin、Susanna Cavallini、Denis Gentili、Francesca Tinti、Massimiliano Cavallini、Nadia Camaioni、Manuela Melucci

  DOI：10.1016/j.tet.2014.03.010

  日期：2014.9

  We report a new class of multifunctional 9,10-dithienylanthracene-based materials having an anthracene pi-core functionalized at the 9,10 positions with thienyl side-arms of different size and type of substitution. MW-assisted double direct arylation reaction is employed for the first time to synthesize the target molecules in one-step, organometallic free conditions, in only 5 min and yields up to 80% rather than by a multi-step Stile coupling taken as conventional reference approach. DFT calculations reveal a molecular conformation characterized by the thienyl rings orthogonal to the anthracene core. Nevertheless, despite the non-coplanar structure, all compounds exhibited highly crystalline cast films emitting blue light, with an extraordinary variability in morphology and hole mobility up to 8x10(-3) cm(2) V-1 s(-1). (C) 2014 Elsevier Ltd. All rights reserved.
• 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.