5'-iodo-5-nitro-[2,2']bithiophene | 163928-51-6

• 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
• 英文名称: 5'-iodo-5-nitro-[2,2']bithiophene
• 英文别名: 2-(5-iodothiophen-2-yl)-5-nitrothiophene
• CAS: 163928-51-6
• 化学式: C₈H₄INO₂S₂
• 分子量: 337.162
• InChiKey: IQROHNXSFRDEIE-UHFFFAOYSA-N

物化性质

• 沸点：
  407.2±45.0 °C(Predicted)
• 密度：
  2.011±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5'-iodo-5-nitro-[2,2']bithiophene 在 氢氧化钾 、 copper(l) iodide 、 四(三苯基膦)钯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 5'-ethynyl-5-nitro-[2,2']bithiophene
  参考文献：
  名称：

  设计、合成、线性和非线性光学性质的共轭 (Porphinato) 锌 (II) 基供体-受体发色团具有硝基噻吩和硝基低聚噻吩电子接受部分

  摘要：

  使用涉及[5-溴-15-三异丙基甲硅烷基乙炔基-10,20-二芳基卟吩基]的金属催化交叉偶联反应合成了一系列广泛的基于共轭（卟啉）锌（II）的发色团，这些发色团具有硝基噻吩和硝基低聚噻吩电子接受部分锌 (II) 和不寻常的富含电子的铃木卟啉合成子，[5-(4-二甲氨基苯基乙炔基)-15-(4',4',5',5'-四甲基 [1',3',2'] dioxaborolan-2'-yl)-10,20-diarylporphinato]zinc(II)，具有适当官能化的芳基和噻吩基前体。这些供体-受体发色团具有以 5-硝基封端的苯硫基、[2,2']联苯硫基和 [2,2';5',2'']三联苯单元；一系列结构的特点是这些受体部分直接附加到卟啉大环中间碳位置，而第二组利用中间的中间乙炔基部分来修饰卟啉与噻吩的结合。这些化合物的动态超极化率是通过在 800 和 1300 nm 的基本入射辐射波长 (λ(inc))

  DOI：

  10.1021/ja0402553
• 作为产物：
  描述：

  2-硝基-5-噻吩-2-基噻吩 在 碘 、 溶剂黄146 、 mercury(II) oxide 作用下， 反应 4.3h， 以79%的产率得到5'-iodo-5-nitro-[2,2']bithiophene
  参考文献：
  名称：

  设计、合成、线性和非线性光学性质的共轭 (Porphinato) 锌 (II) 基供体-受体发色团具有硝基噻吩和硝基低聚噻吩电子接受部分

  摘要：

  使用涉及[5-溴-15-三异丙基甲硅烷基乙炔基-10,20-二芳基卟吩基]的金属催化交叉偶联反应合成了一系列广泛的基于共轭（卟啉）锌（II）的发色团，这些发色团具有硝基噻吩和硝基低聚噻吩电子接受部分锌 (II) 和不寻常的富含电子的铃木卟啉合成子，[5-(4-二甲氨基苯基乙炔基)-15-(4',4',5',5'-四甲基 [1',3',2'] dioxaborolan-2'-yl)-10,20-diarylporphinato]zinc(II)，具有适当官能化的芳基和噻吩基前体。这些供体-受体发色团具有以 5-硝基封端的苯硫基、[2,2']联苯硫基和 [2,2';5',2'']三联苯单元；一系列结构的特点是这些受体部分直接附加到卟啉大环中间碳位置，而第二组利用中间的中间乙炔基部分来修饰卟啉与噻吩的结合。这些化合物的动态超极化率是通过在 800 和 1300 nm 的基本入射辐射波长 (λ(inc))

  DOI：

  10.1021/ja0402553

文献信息

• Dithienylnaphthalenes and quaterthiophenes substituted with electron-withdrawing groups as n-type organic semiconductors for organic field-effect transistors
  作者：Lucia Feriancová、Marek Cigáň、Jozef Kožíšek、Katarína Gmucová、Vojtech Nádaždy、Tibor Dubaj、Michal Sobota、Miroslav Novota、Martin Weis、Martin Putala

  DOI：10.1039/d2tc01238c

  日期：——

  based on an analogy with efficient p-type semiconductors, by introducing electron-withdrawing groups while maintaining the symmetry of the molecules upon omitting one thiophene unit on each side of the oligoaryl core. Two series of dithienylnaphthalenes and quaterthiophenes substituted with various electron-withdrawing groups have been synthesised using Suzuki or Stille cross-coupling, and Knoevenagel

  我们在此报告了一种成功的 n 型半导体材料设计策略，该策略基于与有效 p 型半导体的类比，通过引入吸电子基团，同时在寡芳基核的每一侧省略一个噻吩单元时保持分子的对称性。以 Suzuki 或 Stille 交叉偶联和 Knoevenagel 缩合为关键步骤合成了两个系列的被各种吸电子基团取代的二噻吩基萘和四噻吩。比较了与吸电子基团效应相关的理论和实验分子性质。DFT计算和实验确定的前沿轨道之间的能隙值均显示出按全氟烷基、酰基、全氟酰基、硝基、烷基二氰基乙烯基和全氟烷基二氰基乙烯基在这两个系列中。五种衍生物的 X 射线分析揭示了具有人字形或层状填充图案的寡芳基核心的几乎平面几何形状。四噻吩的晶体结构呈现出 s-与理论预测相反，晶体中外部噻吩之间的顺式构象。基于羰基的化合物在OFET器件中作为有源层表现出n型行为，电子迁移率高达0.57 cm 2 V -1 s -1。
• Synthesis and Solvatochromic Properties of Donor-Acceptor-Substituted Oligothiophenes
  作者：Franz Effenberger、Frank Wuerthner、Felix Steybe

  DOI：10.1021/jo00112a032

  日期：1995.4

  The Pd-catalyzed cross coupling reaction of electron donor-substituted thiophenes 1 with electron acceptor-substituted halothiophenes 2,10 via organozinc intermediates or organotin compounds 5 to give bi-, ter-, and quaterthiophenes 3, 4, 6, 8, 12, 13, and 14 is described. (Dimethylamino)-bithiophenes 8 with acceptor groups of varying reactivity were prepared via 5d in 60-80% yield, whereas bithiophenes 6d,e were obtained as a mixture with phenylthiophenes 7d,e. Symmetrical substituted byproducts 11 were formed in the conversion of 1b with bromothiophenes 10 via organozinc compounds yielding oligothiophenes 6b and 12. The ter- and quaterthiophenes 13 and 14 were isolated in about 50-70% yield. The electronic interactions between donor and acceptor end groups in the conjugated bithiophenes 3, 4, and 8 are expressed in the intensive and markedly solvatochromic CT transitions. The solvatochromic behavior of 3, 4, and 8 was determined by linear regression analyses of absorption maxima in 11 solvents, whereby bithiophene 3d was found to be a very appropriate indicator dye whose absorption wavenumbers ($) over bar nu(max)(3d) in aliphatic and dipolar aprotic and-on consideration of the polarizability correction term d delta-in aromatic and chlorinated solvents excellently correlate with the pi* values defined by Kamlet and Taft.
• Synthesis and characterization of push–pull organic semiconductors with various acceptors for solution-processed small molecule organic solar cells
  作者：Nara Cho、Jooyoung Kim、Kihyung Song、Jae Kwan Lee、Jaejung Ko

  DOI：10.1016/j.tet.2012.03.061

  日期：2012.5

  New efficient push-pull organic semiconductors comprising of the bis(9,9-dimethyl-9H-fluoren-2-yl) aniline (bisDMFA) donor and the various acceptors such as NO2, DCBP, and TCF, which were linked with bithiophene or vinyl bithiophene pi-conjugation bridges, were synthesized, and their photovoltaic characteristics were investigated in solution-processed small molecule organic solar cells (SMOSCs). The intramolecular charge transfers of these materials were effectively appeared in between bisDMFA donor and acceptors, depending on the electron-withdrawing strength of acceptors. The organic semiconductors having NO2 and DCBP acceptors exhibited the most efficient photovoltaic performance, showing power conversion efficiency (PCE) of 1.98% (+/- 0.17) and 2.01% (+/- 0.21), respectively. When the TiOx thin layer was treated on photoactive layer, the organic semiconductor having NO2 showed the best PCE of 2.70% with short circuit current of 8.19 mA/cm(2), fill factor of 0.40, and open circuit voltage of 0.83 V in SMOSC devices. (C) 2012 Elsevier Ltd. All rights reserved.