2-phenylbenzimidazole-5,6-dicarbonitrile | 825613-16-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-phenylbenzimidazole-5,6-dicarbonitrile
• 英文别名: 2-phenyl-1H-benzo[d]imidazole-5,6-dicarbonitrile；1H-Benzimidazole-5,6-dicarbonitrile, 2-phenyl-；2-phenyl-1H-benzimidazole-5,6-dicarbonitrile
• CAS: 825613-16-9
• 化学式: C₁₅H₈N₄
• 分子量: 244.255
• InChiKey: HCPMWHDOUZIHNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-phenylbenzimidazole-5,6-dicarbonitrile 在 cobalt(II) chloride 作用下， 以30%的产率得到(23,73,123,173-tetraphenyl-tetrabenzimidazolo[5,6-b,g,l,q]-5,10,15,20-tetraazaporphyrinato)cobalt(II)
  参考文献：
  名称：

  Metal Complexes of Phthalocyanine Structural Analogs with Oxygen- or Nitrogen-containing Heterorings. Synthesis and Properties

  摘要：

  Nucleophilic substitution of the bromine atom and nitro group in 4-bromo-5-nitrophthalodinitrile and reduction of 4-benzoylamino-5-nitrophthalodinitrile gave, respectively, tribenzo[b,e,g][1,4]dioxocine-7,8-dicarbonitrile and 2-phenylbenzimidazole-5,6-dicarbonitrile. These compounds were used to synthesize new structural analogs of phthalocyanine, having oxygen- and nitrogen-containing heterorings, (tetratribenzo[b,e,g][1,4]dioxocino[7,8-b,g,l,q]-5,10,15,20-tetraazaporphyrinato)copper(II) and (23,73,123,173-tetraphenyl-tetrabenzimidazolo[5,6-b,g,l,q]-5,10,15,20-tetraazaporphyrinato)cobalt(II). Spectral properties of the resulting complexes were studied.

  DOI：

  10.1023/b:rugc.0000039096.32453.12
• 作为产物：
  描述：

  1,2-二硝基苯 在 盐酸 、 硫酸 、 碘 、 氧气 、 三氯化铁 、 铁粉 作用下， 以 N-甲基吡咯烷酮 、 乙醇 为溶剂， 反应 31.0h， 生成 2-phenylbenzimidazole-5,6-dicarbonitrile
  参考文献：
  名称：

  Synthesis of a New trans-A₂B₂ Phthalocyanine Motif as a Building Block for Rodlike Phthalocyanine Polymers

  摘要：

  Polyphthalocyanines have potential application in the development of electronic materials. One-dimensional polyphthalocyanines are accessible through monomers having a trans-A(2)B(2) structure, but the preparation of a truly linear polyphthalocyanine is challenging because of limitations imposed by the geometry of phthalocyanines and the methodology for their synthesis. Benzimidazoporphyrazines are a known class of extra-annulated phthalocyanines. A trans-A(2)B(2) benzimidazoporphyrazine is geometrically suitable for the preparation of rodlike polymers. A new synthesis of benzimidazoporphyrazines is presented as a stepping stone to the synthesis of trans-A(2)B(2) benzimidazoporphyrazines.

  DOI：

  10.1021/jo052122l

文献信息

• Substituted benzazoloporphyrazines for polymerization and surface attachment and articles formed therefrom
  申请人：Youngblood W. Justin

  公开号：US20110015388A1

  公开（公告）日：2011-01-20

  The present invention provides an article of manufacture formed from a substrate and a benzazoloporphyrazine bound to the substrate. The article may take a variety of different forms and may be for example an electrochromic display, a molecular capacitor, a battery, a solar cell, or a molecular memory device. Methods of making such articles, along with compounds, methods and intermediates useful for making such benzazoloporphyrazines, are also described.

  本发明提供了一种由基板和与基板结合的苯并咔唑卟啉制成的制品。该制品可以采用各种不同形式，例如电致变色显示器、分子电容器、电池、太阳能电池或分子存储器件。还描述了制造这种制品的方法，以及用于制造这种苯并咔唑卟啉的化合物、方法和中间体。
• 蛍光標識剤、光線力学治療剤およびフタロシアニン
  申请人：東洋インキＳＣホールディングス株式会社

  公开号：JP2020105170A

  公开（公告）日：2020-07-09

  【課題】蛍光標識剤および光線力学治療剤に適した蛍光強度、耐光性、一重項酸素発生能に優れた特性を有するフタロシアニンを提供すること。【解決手段】中心金属がＡｌまたはＳｉのフタロシアニンであり、該金属に結合する水酸基等の数は、Ａｌの場合は１であり、Ｓｉの場合は２であることを特徴とする蛍光標識剤。【選択図】図１

  提供具有适用于荧光标记剂和光动力治疗剂的荧光强度、耐光性和优良的单重态氧产生能力的邻菲啰啉。所述荧光标记剂的特征是中心金属为Al或Si的邻菲啰啉，结合到该金属的羟基数量为1，对于Al的情况，对于Si的情况则为2。【选定图】图1
• The Transfer Dehydrogenation Method Enables a Family of High Crystalline Benzimidazole‐linked Cu (II)‐phthalocyanine‐based Covalent Organic Frameworks Films
  作者：Qingsong Zhang、Zhiheng Zhu、Liping Liu、Haojie Huang、Xianjie Chen、Yangshuang Bian、Mingchao Shao、Xiaofang Wei、Chengyu Wang、Dong Wang、Jichen Dong、Yunlong Guo、Yongfa Zhu、Yunqi Liu

  DOI：10.1002/anie.202319027

  日期：2024.5.6

  transfer dehydrogenation method to prepare a novel series of imidazole-linked phthalocyanine Cu (II)-based covalent organic frameworks (BICuPc-COFs) films and powders. The high crystalline BICuPc-COFs films that possess intrinsic conductivity (0.022–0.218 S/m) were fabricated into synaptic devices, which have small source-drain voltage (VDS=1 V) and response light from visible to near-infrared.

  在这项工作中，我们提出了一种转移脱氢方法来制备一系列新型咪唑连接的酞菁铜（II）基共价有机骨架（BICuPc-COF）薄膜和粉末。具有本征电导率（0.022-0.218 S/m）的高结晶BICuPc-COFs薄膜被制成突触器件，该器件具有较小的源漏电压（V DS = 1 V）和从可见光到近红外的响应光。
• Synthesis of a New <i>trans</i>-A₂B₂ Phthalocyanine Motif as a Building Block for Rodlike Phthalocyanine Polymers
  作者：W. Justin Youngblood

  DOI：10.1021/jo052122l

  日期：2006.4.1

  Polyphthalocyanines have potential application in the development of electronic materials. One-dimensional polyphthalocyanines are accessible through monomers having a trans-A(2)B(2) structure, but the preparation of a truly linear polyphthalocyanine is challenging because of limitations imposed by the geometry of phthalocyanines and the methodology for their synthesis. Benzimidazoporphyrazines are a known class of extra-annulated phthalocyanines. A trans-A(2)B(2) benzimidazoporphyrazine is geometrically suitable for the preparation of rodlike polymers. A new synthesis of benzimidazoporphyrazines is presented as a stepping stone to the synthesis of trans-A(2)B(2) benzimidazoporphyrazines.
• Metal Complexes of Phthalocyanine Structural Analogs with Oxygen- or Nitrogen-containing Heterorings. Synthesis and Properties
  作者：V. E. Maizlish、G. P. Shaposhnikov、O. V. Balakireva、M. A. Zharnikova、I. G. Abramov、S. A. Ivanovskii、A. V. Smirnov

  DOI：10.1023/b:rugc.0000039096.32453.12

  日期：2004.5

  Nucleophilic substitution of the bromine atom and nitro group in 4-bromo-5-nitrophthalodinitrile and reduction of 4-benzoylamino-5-nitrophthalodinitrile gave, respectively, tribenzo[b,e,g][1,4]dioxocine-7,8-dicarbonitrile and 2-phenylbenzimidazole-5,6-dicarbonitrile. These compounds were used to synthesize new structural analogs of phthalocyanine, having oxygen- and nitrogen-containing heterorings, (tetratribenzo[b,e,g][1,4]dioxocino[7,8-b,g,l,q]-5,10,15,20-tetraazaporphyrinato)copper(II) and (23,73,123,173-tetraphenyl-tetrabenzimidazolo[5,6-b,g,l,q]-5,10,15,20-tetraazaporphyrinato)cobalt(II). Spectral properties of the resulting complexes were studied.