4,5-dibromo-3,6-dibutoxyphthalonitrile | 288303-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,5-dibromo-3,6-dibutoxyphthalonitrile
• 英文别名: 1,2-Benzenedicarbonitrile, 4,5-dibromo-3,6-dibutoxy-；4,5-dibromo-3,6-dibutoxybenzene-1,2-dicarbonitrile
• CAS: 288303-40-2
• 化学式: C₁₆H₁₈Br₂N₂O₂
• 分子量: 430.139
• InChiKey: HAAHMAILBWIUSO-UHFFFAOYSA-N

物化性质

• 沸点：
  474.5±45.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5-dibromo-3,6-dibutoxyphthalonitrile 在 bis-triphenylphosphine-palladium(II) chloride 氨 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.0h， 生成 5,8-dibutoxy-6,7-di([2,2'-bithiophene]-5-yl)-1,3-dihydro-1,3-diiminoisoindole
  参考文献：
  名称：

  Elongation of the π-System of Phthalocyanines by Introduction of Thienyl Substituents at the Peripheral β Positions. Synthesis and Characterization

  摘要：

  1,4,8,11,15,18,22,25-Octabutoxyphthalocyanines ((OBu)(8)Pcs) having eight 2-thienyl (1) and [2,2 ' -bithiophene] -5-yl (2) groups at beta positions and their zinc(II) and cobalt(II) derivatives were prepared from 2-thienyl- (3) or [2,2 ' -bithiophenel-5-yl (4)-substituted phthalonitriles in moderate to good yields. The electronic absorption spectra of the Pes showed red-shifted Q-bands relative to P-unsubstituted (OBu)8Pcs. The longer substituent, the [2,2 ' -bithiophene]-5-yl group, is more effective than the 2-thienyl group in enlarging the a-conjugated system of the Pcs. The ring oxidation potential obtained by cyclic voltammetry shifted cathodically with increasing chain length, indicating destabilization of the HOMOs. Due to the shift of the Q-band, 2-thienyl- and [2,2 ' -bithiophene]-5-yl-substituted Pes exhibit a remarkable color change from the original green color.

  DOI：

  10.1021/jo010384r
• 作为产物：
  描述：

  3,6-二羟基邻苯二甲腈 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 生成 4,5-dibromo-3,6-dibutoxyphthalonitrile
  参考文献：
  名称：

  一些 3,6-二取代邻苯二甲腈的路线和从中衍生的酞菁实例：概述

  摘要：

  本文回顾了一些合成途径，这些途径提供了 3,6-二取代酞腈，这是合成 1,4,8,11,15,18,22,25-八取代酞菁衍生物的前体。评价了使用 Diels-Alder 反应合成 3,6-二烷基、3,6-二烷氧基甲基、3,6-二烯基和 3,6-二苯基邻苯二甲腈的早期路线。然而，审查的重点集中在 2,3-二氰基氢醌作为获得 3,6-二取代邻苯二甲腈的起始原料的范围和应用。使用 2,3-二氰基氢醌的最早例子涉及其 O-烷基化以提供 3,6-二烷氧基邻苯二甲腈。这些是近红外吸收酞菁衍生物的直接前体。2,3-二氰基氢醌的三氟甲磺酸化扩展了该化合物用于合成酞菁的范围；ñAr 反应并容易与硫醇反应生成 3,6-双（烷基硫烷基）和 3,6-双（芳基硫烷基）邻苯二甲腈。3,6-双（苯基硒基）邻苯二甲腈最近也从相同的前体中获得。从中获得的酞菁衍生物通常表现出强烈的红移 Q 波段吸收，该吸收对中心金属离子特别敏感。2

  DOI：

  10.1142/s108842461330005x

文献信息

• 1,4-Dibutoxy-2,3-di(4-pyridyl)-8,11,15,18,22,25-hexakis(hexyl)phthalocyaninato zinc, a self-assembled coordination polymer in the solid state
  作者：Shaya Y. Al-Raqa、Michael J. Cook、David L. Hughes

  DOI：10.1039/b207873m

  日期：2003.12.19

  The title compound forms intermolecular zinc–nitrogen coordinated species in solution and self-assembles to form a coordination polymer in the solid state, the X-ray structure for which shows that the unit cell contains eight macrocycle units in two chains comprising both enantiomeric forms as ABBA/BAAB sequences.

  标题化合物在溶液中形成分子间锌-氮配位物质，并自组装形成固态配位聚合物，其X射线结构显示晶胞在两条链中包含八个大环单元，包含两种对映体形式： ABBA/BAAB 序列。
• Ferrocenyl Phthalocyanine as Donor in Non-Poly(3-hexylthiophen-2,5-diyl) Bulk Heterojunction Solar Cell
  作者：Ilgın Nar、Armağan Atsay、Ahmet Altındal、Esin Hamuryudan、Makbule B. Koçak、Ahmet Gül

  DOI：10.1002/chem.201801340

  日期：2018.5.11

  Bulk heterojunction (BHJ) solar cells might one day play a vital role in realizing low‐cost and environmentally benign photovoltaic devices. In this work, a BHJ solar cell was designed, based on a hexadeca‐substituted phthalocyanine (FcPc) with ferrocenyl linked to the phthalocyanine ring. Next, we sought to obtain more quantitative information about the usability of this newly synthesized compound

  整块异质结（BHJ）太阳能电池有一天可能在实现低成本和对环境无害的光伏设备中起至关重要的作用。在这项工作中，基于十六烷基取代的酞菁（FcPc）设计了BHJ太阳能电池，其中二茂铁基连接到酞菁环上。接下来，我们寻求获得更多有关此新合成的化合物作为BHJ太阳能电池供体材料的可用性的定量信息。因此，具有氧化铟锡/聚（3,4-乙撑二氧噻吩）：聚（苯乙烯磺酸盐）/ FcPc：[6,6]-苯基-C61-丁酸甲酯（PCBM）的结构的BHJ共混物/制备并表征了LiF / Al。还研究了混合比（0.5–2.0）对BHJ太阳能电池参数的影响。在优化条件下，FcPc和基于PCBM共混物的BHJ太阳能电池获得了有趣的结果。我们在这里提出的结果表明，采用FcPc作为供体的BHJ器件在开发高效非聚（3-己基噻吩-2,5-二基）光伏器件方面具有巨大潜力。
• π-Extended hexadeca-substituted cobalt phthalocyanine as an active layer for organic field-effect transistors
  作者：Ilgın Nar、Armağan Atsay、Hande Pekbelgin Karaoğlu、Ahmet Altındal、Esin Hamuryudan

  DOI：10.1039/c8dt02948b

  日期：——

  The structural modification of the phthalocyanine skeleton with a hexadeca substitution pattern is a promising approach for the fabrication of active layers for OFETs.

  使用十六取代模式对酞菁骨架进行结构修饰是制备OFETs活性层的一种有前途的方法。
• Phthalocyaninodehydroannulenes
  作者：Michael J. Cook、Martin J. Heeney

  DOI：10.1002/1521-3765(20001103)6:21<3958::aid-chem3958>3.0.co;2-y

  日期：2000.11.3

  4-Bromo- and 4,5-dibromo-3,6-dibutoxyphthalonitrile have been prepared and treated with 3,6-didecylphthalonitrile in cross tetramerisation reactions in the presence of nickel acetate to afford monobromo- and dibromo-dibutoxyhexadecylphthalocyaninato nickel(II) complexes. Sonogashira and Stille coupling reactions on these compounds displaced the bromine substituents by ethynyl groups. Oxidative coupling of the monoethynyl derivatised nickel phthalocyanine afforded a butadiynyl-linked dinuclear phthalocyanine. The corresponding coupling reaction of the diethynylated phthalocyanine gave a mixture of phthalocyaninodehydroannulenes. Separation of the mixture yielded the diphthalocyaninodehydro[12]annulene as the major product. Electrospray mass spectrometry provides evidence for its aggregation in solution. The corresponding cyclic trimer, the triphthalocyaninodehydro[18]annulene. has been identified as a minor product. Both compounds show a large splitting of the Q-band absorption in the visible region spectrum, Most of the mononuclear phthalocyanine precursors exhibit discotic liquid crystal behaviour. The diphthalocyaninodehydro[12]annulene also enters a mobile phase on heating, hut undergoes an irreversible change at 220 degreesC. MALDI-TOF mass spectrometry of the product reveals that the compound undergoes oligomerisation at this temperature.
• SUBSTITUTED PHTHALOCYANINES AND THEIR PRECURSORS
  申请人：Gentian AS

  公开号：EP1238016A1

  公开（公告）日：2002-09-11