4,5-二碘苯-1,2-二甲醛 | 875535-39-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4,5-二碘苯-1,2-二甲醛
• 英文名称: 4,5-diiodobenzene-1,2-dicarbaldehyde
• 英文别名: 4,5-diiodo-1,2-Benzenedicarboxaldehyde；4,5-diiodophthalaldehyde
• CAS: 875535-39-0
• 化学式: C₈H₄I₂O₂
• 分子量: 385.928
• InChiKey: VPDVREVAJYUUOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-二碘苯-1,2-二甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 氢氧化钾 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 2,3,9,10-tetrakis(triisopropylsilylethynyl)-6,13-pentacenequinone
  参考文献：
  名称：

  Design, Synthesis, and Properties of New Derivatives of Pentacene

  摘要：

  Stable, soluble ethynylated derivatives of pentacene (9a-c) were synthesized, and the ethynyl moieties on the terminal rings were used to tune the electronic properties of these compounds. Their oxidation potentials are higher and their reduction potentials are lower than those of pentacene. The HOMO-LUMO gaps are among the lowest reported for pentacene derivatives.

  DOI：

  10.1021/jo0522198
• 作为产物：
  描述：

  邻苯二甲酸亚胺 在 硫酸 、 硼烷 、 碘 、 potassium hydroxide 作用下， 生成 4,5-二碘苯-1,2-二甲醛
  参考文献：
  名称：

  通过设计外围取代基来 控制氯硼（iii）和氟硼（iii）亚萘酞菁的分子堆积†

  摘要：

  通过Sonogashira偶联六碘亚萘酞菁与取代的乙炔，制备了具有大偶极矩的氯硼烷（III）和氟硼（III）六（1-炔基）-和六（2-芳基乙炔基）亚萘菁。通过乙炔键在周边引入丁基或更长烷基会导致较低的熔点和较高的二氯甲烷溶解度。流延膜的X射线衍射（XRD）图表明，具有B-F键的六（2-（4-己基苯基）乙炔基）-和六（2-（4-己氧基苯基）乙炔基）亚萘菁被填充在盘状中六方柱状相，晶格常数a = 59–64Å，堆积距离c= 4.7–4.8Å。这些B–F衍生物薄膜的可见光谱中的Q带发生了蓝移，从而支持了堆积柱中H聚集体的形成。偏光光学显微镜显示，这些具有B-F键的亚萘酞菁在180°C时表现出中间相。这些亚萘酞菁在180°C的XRD证实是二维六方相。带有B–Cl键的相应衍生物的X射线衍射表明，它们要么是非晶态的，要么是结晶度较低的。我们建议，由于F的范德华半径比Cl小，因此BF基团中的氟原子可以嵌

  DOI：

  10.1039/c7ra11104e

文献信息

• Soluble n-type pentacene derivatives as novel acceptors for organic solar cells
  作者：Yee-Fun Lim、Ying Shu、Sean R. Parkin、John E. Anthony、George G. Malliaras

  DOI：10.1039/b818693f

  日期：——

  6,13-Bis(triisopropylsilylethynyl) (TIPS)-pentacene has proven to be a promising soluble p-type material for organic thin film transistors as well as for photovoltaics. In this work, we show that adding electron-withdrawing nitrile functional groups to TIPS-pentacene turns it into an n-type material, which can be used as an acceptor for organic solar cells. Several new cyanopentacenes with different trialkylsilyl functional groups have been synthesized. The HOMO–LUMO energy levels can be tuned by varying the number of nitrile groups, while the trialkylsilyl groups control crystal packing and film morphology. Solar cells were fabricated from a blend of poly(3-hexylthiophene) (P3HT) as the donor and the cyanopentacenes as acceptors, and we found that the acceptors that stack in a 1D “sandwich-herringbone” exhibited the best performance of derivatives in this study. A solar cell fabricated from a blend of P3HT and 2,3-dicyano-6,13-bis-(tricyclopentylsilylethynyl)pentacene (2,3-CN2-TCPS-Pn) exhibited a power conversion efficiency of 0.43% under 100 mW cm−2AM 1.5 illumination.

  6,13-双（三异丙基硅基乙炔基）(TIPS)-五聚烯已经被证明是一种有前景的可溶性p型材料，适用于有机薄膜晶体管和光伏材料。在本研究中，我们展示了通过向TIPS-五聚烯中添加强电子吸引的氰基功能团，可以将其转变为n型材料，进而作为有机太阳能电池的受体。我们合成了几种不同三烷基硅基功能团的新氰基五聚烯。通过改变氰基数量可以调节HOMO-LUMO能级，而三烷基硅基团则控制晶体堆积和薄膜形态。我们用聚（3-己基噻吩）（P3HT）作为供体，与氰基五聚烯混合制成太阳能电池，发现以1D“夹心人字形”堆叠的受体在该研究中表现出最佳性能。由P3HT和2,3-二氰基-6,13-双（三环戊基硅基乙炔基）五聚烯（2,3-CN2-TCPS-Pn）混合制成的太阳能电池在100 mW cm−2 AM 1.5照明下展现出0.43%的光电转换效率。
• Synthesis and optoelectronic properties of hexachloro- and hexaiodosubnaphthalocyanines as organic electronic materials
  作者：Koji Yamamoto、Akuto Takagi、Miyako Hada、Ryosuke Taniwaki、Tadashi Mizutani、Yoshifumi Kimura、Yuko Takao、Kazuyuki Moriwaki、Fukashi Matsumoto、Takatoshi Ito、Toshiyuki Iwai、Koichi Hida、Takumi Mizuno、Toshinobu Ohno

  DOI：10.1016/j.tet.2016.06.064

  日期：2016.8

  Chloroboron(III) hexachloro- and hexaiodosubnaphthalocyanines were prepared, and their solubility, electronic absorption spectroscopy, fluorescence emission spectroscopy and HOMO/LUMO energy levels were evaluated. These subnaphthalocyanines showed lower HOMO/LUMO energies than the parent subnaphthalocyanine by 0.13-0.39 eV. The optical band gap decreased in the order: hexafluoro>hexachloro->unsubstituted>hexaiodo-subnaphthalocyanine. Fluorescence quantum yield of hexaiodosubnaphthalocyanine was 0.05, significantly lower than those of the parent, hexafluoro- and hexachloro-subnaphthalocyanines whose quantum yields ranged from 0.2 to 0.22, indicating that the heavy atom effects of iodine work effectively. (C) 2016 Elsevier Ltd. All rights reserved.