N,N'-(1,4-phenylene)bis(2-bromo-N-dodecylthiophene-3-carboxamide) | 1491134-56-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N'-(1,4-phenylene)bis(2-bromo-N-dodecylthiophene-3-carboxamide)
• 英文别名: 2-bromo-N-[4-[(2-bromothiophene-3-carbonyl)-dodecylamino]phenyl]-N-dodecylthiophene-3-carboxamide
• CAS: 1491134-56-5
• 化学式: C₄₀H₅₈Br₂N₂O₂S₂
• 分子量: 822.853
• InChiKey: MSDBDWLOVIVSST-UHFFFAOYSA-N

物化性质

• 沸点：
  806.6±65.0 °C(predicted)
• 密度：
  1.249±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16.5
• 重原子数：
  48
• 可旋转键数：
  26
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  97.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-(1,4-phenylene)bis(2-bromo-N-dodecylthiophene-3-carboxamide) 在 sodium acetate 、 palladium diacetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 21.0h， 以70%的产率得到10,20-Didodecyl-5,15-dithia-10,20-diazapentacyclo[11.7.0.03,11.04,8.014,18]icosa-1(13),2,4(8),6,11,14(18),16-heptaene-9,19-dione
  参考文献：
  名称：

  串联直接芳基化获得的π-扩展内酰胺融合共轭低聚物的合成及场效应晶体管的应用

  摘要：

  通过串联直接芳基化反应合成了五个π延伸的内酰胺融合共轭低聚物（5FO，5FS，4FPO，4FPS和R-4FPO）。在第二步骤中应用分子间氧化直接芳基化。这些共轭低聚物具有可通过理论计算预测的FMO能量微调，并且具有出色的热稳定性。与其他相比，带有四氟吡啶的4FPO和4FPS表现出较低的LUMO能级（分别为-3.20 eV和-3.39 eV）。基于X射线晶体学，4FPO被发现具有人字形晶体堆积和相当大的电子转移积分值（137 meV）。基于4FPO的底栅，底接触FET器件由于在SiO 2衬底上进行边沿对准而显示出5.2×10 -3  cm 2  V -1  s -1的电子迁移率。

  DOI：

  10.1002/chem.201801399
• 作为产物：
  描述：

  对苯二胺 在 sodium hydride 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 8.67h， 生成 N,N'-(1,4-phenylene)bis(2-bromo-N-dodecylthiophene-3-carboxamide)
  参考文献：
  名称：

  Novel Thiophene–Phenylene–Thiophene Fused Bislactam-Based Donor–Acceptor Type Conjugate Polymers: Synthesis by Direct Arylation and Properties

  摘要：

  Three new donor acceptor copolymers based on thiophene phenylene thiophene fused bislactam and various donors (3,4-dodecylthiophene, 4,4'-didodecyl-2,2'-bithiophene, and ethylenedioxythiophene) were synthesized, characterized, and used in field-effect transistors. Polycondensation was performed using nonactivated thiophene derivatives by employing palladium-catalyzed direct arylation under phosphine-free conditions. This method is superior to traditional cross-coupling polymerization because it requires fewer synthetic operations and does not employ toxic organometallic intermediates. Regioselective polymers can also be generated by using beta-substituted thiophene derivatives. The studied polymers were tested in a bottom gate top contact thin film transistor (OTFT) architecture. The best electronic performance was shown by polymer P3, with enhanced pi-conjugation due to the appearance of intramolecular attractive interactions.

  DOI：

  10.1021/ma4018907

文献信息

• Novel Thiophene–Phenylene–Thiophene Fused Bislactam-Based Donor–Acceptor Type Conjugate Polymers: Synthesis by Direct Arylation and Properties
  作者：Mithrabinda K. Poduval、Paula Mayorga Burrezo、Juan Casado、J. Teodomiro López Navarrete、Rocío Ponce Ortiz、Tae-Hyun Kim

  DOI：10.1021/ma4018907

  日期：2013.12.10

  Three new donor acceptor copolymers based on thiophene phenylene thiophene fused bislactam and various donors (3,4-dodecylthiophene, 4,4'-didodecyl-2,2'-bithiophene, and ethylenedioxythiophene) were synthesized, characterized, and used in field-effect transistors. Polycondensation was performed using nonactivated thiophene derivatives by employing palladium-catalyzed direct arylation under phosphine-free conditions. This method is superior to traditional cross-coupling polymerization because it requires fewer synthetic operations and does not employ toxic organometallic intermediates. Regioselective polymers can also be generated by using beta-substituted thiophene derivatives. The studied polymers were tested in a bottom gate top contact thin film transistor (OTFT) architecture. The best electronic performance was shown by polymer P3, with enhanced pi-conjugation due to the appearance of intramolecular attractive interactions.
• Synthesis and Field‐Effect Transistor Application of π‐Extended Lactam‐Fused Conjugated Oligomers obtained by Tandem Direct Arylation
  作者：Koji Takagi、Shun‐ya Yamamoto、Kenji Tsukamoto、Yuto Hirano、Mitsuo Hara、Shusaku Nagano、Yutaka Ie、Daisuke Takeuchi

  DOI：10.1002/chem.201801399

  日期：2018.9.20

  Five π‐extended lactam‐fused conjugated oligomers (5FO, 5FS, 4FPO, 4FPS, and R‐4FPO) were synthesized by the tandem direct arylation. The intermolecular oxidative direct arylation was applied in the second step. These conjugated oligomers had fine‐tuned FMO energies predictable by the theoretical calculation and excellent thermal stabilities. 4FPO and 4FPS bearing tetrafluoropyridine exhibited lower

  通过串联直接芳基化反应合成了五个π延伸的内酰胺融合共轭低聚物（5FO，5FS，4FPO，4FPS和R-4FPO）。在第二步骤中应用分子间氧化直接芳基化。这些共轭低聚物具有可通过理论计算预测的FMO能量微调，并且具有出色的热稳定性。与其他相比，带有四氟吡啶的4FPO和4FPS表现出较低的LUMO能级（分别为-3.20 eV和-3.39 eV）。基于X射线晶体学，4FPO被发现具有人字形晶体堆积和相当大的电子转移积分值（137 meV）。基于4FPO的底栅，底接触FET器件由于在SiO 2衬底上进行边沿对准而显示出5.2×10 -3  cm 2  V -1  s -1的电子迁移率。