2-(tridecafluorohexyl)thiophene | 128032-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(tridecafluorohexyl)thiophene
• 英文别名: 2-(1-perfluorohexyl)thiophene；2-Perfluoro-n-hexylthiophene；2-perfluorohexylthiophene；Thiophene, 2-(tridecafluorohexyl)-；2-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)thiophene
• CAS: 128032-22-4
• 化学式: C₁₀H₃F₁₃S
• 分子量: 402.179
• InChiKey: QALDKDRKOUMDGV-UHFFFAOYSA-N

物化性质

• 沸点：
  92-93 °C(Press: 30 Torr)
• 密度：
  1.610±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  9,10-二溴蒽 、 2-(tridecafluorohexyl)thiophene 在 palladium diacetate 、 potassium carbonate 、 三甲基丙酮酸 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以70%的产率得到9,10-bis(5-(perfluorohexyl)thiophen-2-yl)anthracene
  参考文献：
  名称：

  Synthesis by MW-assisted direct arylation, side-arms driven self-assembly and functional properties of 9,10-dithienylanthracene orthogonal materials

  摘要：

  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.

  DOI：

  10.1016/j.tet.2014.03.010
• 作为产物：
  描述：

  噻吩 、 1,1,2,2,3,3,4,4,5,5,6,6,6-十三氟己烷-1-磺酰氯 在 tris(triphenylphosphine)ruthenium(II) chloride 作用下， 以 正戊烷 为溶剂， 以77%的产率得到2-(tridecafluorohexyl)thiophene
  参考文献：
  名称：

  Kamigata, Nobumasa; Ohtsuka, Takeshi; Shimizu, Toshio, Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 96, # 1-4, p. 491 - 492

  摘要：

  DOI：

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
• Conjugated polymers with deep LUMO levels for field-effect transistors and polymer–polymer solar cells
  作者：Andong Zhang、Chengyi Xiao、Dong Meng、Qiang Wang、Xiaotao Zhang、Wenping Hu、Xiaowei Zhan、Zhaohui Wang、René A. J. Janssen、Weiwei Li

  DOI：10.1039/c5tc01313e

  日期：——

  thiazole-bridged DPP polymers with deep lowest unoccupied molecular orbital (LUMO) levels were designed for field-effect transistors (FETs) and polymer–polymer solar cells. By introducing thiazole–thiazole coupled segments, perfluoroalkyl side chains or strong electron-deficient naphthalenediimide units into the conjugated backbone the three thiazole-bridged DPP polymers have LUMO levels of −4.0 to −4.4

  为场效应晶体管（FET）和聚合物聚合物太阳能电池设计了三种具有最低最低未占据分子轨道（LUMO）水平的噻唑桥连DPP聚合物。通过将噻唑-噻唑偶联的链段，全氟烷基侧链或强电子缺陷的萘二酰亚胺单元引入共轭骨架，三种噻唑桥连的DPP聚合物的LUMO含量为-4.0至-4.4 eV。三种DPP聚合物在底部接触FET中表现出在近红外区域的光吸收，结晶度和约0.01 cm 2 V -1 s -1的电子迁移率。该聚合物被用作聚合物-聚合物太阳能电池中的电子受体，可提供约0.4％的PCE。PCE低主要是由于短路电流低（J sc）并归因于大的相分离。我们的结果证明了降低共轭聚合物能级的几种有效策略，以便用作光伏电池的通用受体。
• Fluoroalkylation of aromatic compounds with per(poly)fluoroalkyl chlorides initiated by sodium dithionite in DMSO
  作者：Xiao-Ting Huang、Zheng-Yu Long、Qing-Yun Chen

  DOI：10.1016/s0022-1139(01)00442-0

  日期：2001.10

  Treatment of electron-rich aromatic and heteroaromatic. compounds with per(poly)fluoroalkyl chlorides in the presence of sodium dithionite in DMSO gives the corresponding fluoroalkylated products in moderate to good yields. The structures and yields of products depend mainly on the position and electron-donating ability of the substituents on the aromatic compounds. (C) 2001 Elsevier Science B.V. All rights reserved.
• Synthesis of Perfluoroalkyl End-Functionalized Poly(3-hexylthiophene) and the Effect of Fluorinated End Groups on Solar Cell Performance
  作者：Zhenghao Mao、Kiarash Vakhshouri、Cherno Jaye、Daniel A. Fischer、Roshan Fernando、Dean M. DeLongchamp、Enrique D. Gomez、Geneviève Sauvé

  DOI：10.1021/ma301397p

  日期：2013.1.8

  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.
• Polyfluoroalkylation of bromoheterocyclic compounds via perfluoroalkylcopper intermediates
  作者：Grace J. Chen、Christ Tamborski

  DOI：10.1016/s0022-1139(00)81565-1

  日期：1990.1