2,6-bis(pentafluorophenyl)dithieno[3,2-b:2',3'-d]thiophene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻吩类
• 英文名称: 2,6-bis(pentafluorophenyl)dithieno[3,2-b:2',3'-d]thiophene
• 英文别名: DFP-DTT；4,10-Bis(2,3,4,5,6-pentafluorophenyl)-3,7,11-trithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene；4,10-bis(2,3,4,5,6-pentafluorophenyl)-3,7,11-trithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene
• 化学式: C₂₀H₂F₁₀S₃
• 分子量: 528.418
• InChiKey: PSTFBIWHXGUUOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  二噻吩[3,2-B:2',3'-D]噻吩 、 溴五氟苯 在 正丁基锂 、 三丁基氯化锡 、 四(三苯基膦)钯 作用下， 以 乙醚 、 Petroleum ether 、 甲苯 为溶剂， 反应 25.0h， 以49.2%的产率得到2,6-bis(pentafluorophenyl)dithieno[3,2-b:2',3'-d]thiophene
  参考文献：
  名称：

  Functionalized dithieno[2,3-b:3′,2′-d]thiophenes (DTTs) for organic thin-film transistors

  摘要：

  A series of dithieno[2,3-b:3',2'-d]thiophene (DTT;1) derivatives were synthesized and characterized. Facile, one-pot [2 + 1] and [1 + 1 + 1] synthetic methods of DTT were developed, which enabled the efficient realization of a new DTT-based semiconductor series for organic thin-film transistors (OTFTs). These DTTs are end-functionalized with perfluorophenyl (FP-), perfluorobenzoyl (FB-), benzoyl (B-), 2-naphthylcarbonyl (Np-), 2-benzothiazolyl (BS-), 2-thienylcarbonyl (T-), and 2-(5-hexyl)thienylcarbonyl (HT-) groups. The molecular structures of DFP-DTT (3), DFB-DTT (4), FBB-DTT (5), DB-DTT (6), and DNp-TT (7) were determined via single-crystal X-ray diffraction. Our studies reveal that the majority of these carbonyl-containing derivatives exhibit p-channel transport with hole mobilities of up to 0.01 cm(2)/Vs for DB-DTT and DBS-DTT, while perfluorobenzoyl and perfluorophenyl-substituted compounds exhibit n-channel transport with mobilities up to 0.002 cm(2)/Vs for DFB-DTT, 0.03 cm(2)/Vs for FBB-DTT, and 0.07 cm(2)/Vs for DFP-DTT, rendering the latter the DTT derivative currently having the highest electron mobility in OTFT devices. Within this family, the carrier mobility values are strongly dependent upon the semiconductor growth temperature and the dielectric surface treatment. (C) 2010 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.orgel.2010.01.022

文献信息

• Syntheses of 2-(Pentafluorophenyl)thiophene Derivatives via the Palladium-Catalyzed Suzuki Reaction
  作者：Kazuo Takimiya、Naoto Niihara、Tetsuo Otsubo

  DOI：10.1055/s-2005-865335

  日期：——

  Various bis(pentafluorophenyl)-substituted thiophene and selenophene derivatives are effectively synthesized by the palladium-catalyzed Suzuki reaction using pentafluorophenyl boronic acid.

  通过钯催化的 Suzuki 反应，使用五氟苯基硼酸有效地合成了各种双（五氟苯基）取代的噻吩和硒吩衍生物。