2-[4-(1H-pyrrol-2-yl)phenyl]-1H-pyrrole | 141484-83-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-[4-(1H-pyrrol-2-yl)phenyl]-1H-pyrrole
• 英文别名: 2,2'-(1,4-phenylene)bis-1H-pyrrole；1,4-bis(1H-pyrrol-2-yl)benzene；1,4-bis(pyrrol-2-yl)benzene；1,4-Di(azol-2-yl)benzene
• CAS: 141484-83-5
• 化学式: C₁₄H₁₂N₂
• 分子量: 208.263
• InChiKey: SYYNZWCFYZWGTK-UHFFFAOYSA-N

物化性质

• 熔点：
  >400 °C
• 沸点：
  492.6±25.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-乙烯基-2-[4-(1-乙烯基吡咯-2-基)苯基]吡咯 在 mercury(II) diacetate 、 sodium tetrahydroborate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以83%的产率得到2-[4-(1H-pyrrol-2-yl)phenyl]-1H-pyrrole
  参考文献：
  名称：

  Fluorescence quenching and laser photolysis of dipyrrolylbenzenes in the presence of chloromethanes

  摘要：

  Fluorescence quenching of 1,4-bis(1H-pyrrol-1-yl)benzene, 1-(1H-pyrrol-2-yl)-1-(1-vinyl-1H-pyrrol-1-yl)benzene, and 1,4-bis(1-vinyl-1H-pyrrol-2-yl)benzene with chloromethanes (methylene chloride, chloroform, and carbon tetrachloride) in solvents with different polarities follows electron-transfer mechanism. The occurrence of an electron-transfer step is confirmed by formation of short-lived pyrrolylbenzene radical cations. An exception is quenching of fluorescence of 1,4-bis(1-vinyl-1H-pyrrol-2-yl)benzene in n-hexane in the presence of CCl4 and CHCl3 and in pure CCl4. In this case, neutral 1,4-bis(1-vinyl-1H-pyrrol-2-yl)benzene(center dot)-Cl radical is formed via recombination of 1,4-bis(1-vinyl-1H-pyrrol-2-yl)benzene radical cation and chloride anion. A relation was found between the nature of the short-lived species detected by laser photolysis and stable product obtained by stationary photolysis.

  DOI：

  10.1134/s1070363207080166

文献信息

• [EN] UNSYMMETRICAL SALTS, CCC-NHC PINCER METAL COMPLEXES, AND METHODS OF MAKING THE SAME<br/>[FR] SELS ASYMÉTRIQUES, COMPLEXES MÉTALLIQUES À PINCE CCC-NHC, ET LEURS PROCÉDÉS DE FABRICATION
  申请人：UNIV MISSISSIPPI STATE

  公开号：WO2018175659A1

  公开（公告）日：2018-09-27

  Provided herein are unsymmetrical bis(azolium) salts, unsymmetrical CCC-NHC metal complexes, and methods of forming the same. The unsymmetrical bis(azolium) salts include a central aryl ring that is substituted with two heterocyclic rings in an ortho, meta, or para fashion. The unsymmetrical CCC-NHC metal complexes include metalated unsymmetrical bis(azolium) salts. The method of forming the unsymmetrical CCC-NHC metal complexes includes reacting a dihalogenated benzene with a first azole to form a mono(azole)benzene, reacting the mono(azole)benzene with a second azole to form an unsymmetrical bis(azole)benzene, alkylating the unsymmetrical bis(azole)benzene to form an unsymmetrical bis(azolium) salt, and metalating the unsymmetrical bis(azolium) salt to form the unsymmetrical CCC-NHC metal complex. Also provided are a bis-ligated CCC-NHC metal complex and an unsymmetrical bimetallic complex.

  本文提供了非对称双(唑)盐、非对称CCC-NHC金属配合物以及其形成方法。非对称双(唑)盐包括一个中心芳香环，该环被两个杂环环取代，可以是邻位、间位或对位。非对称CCC-NHC金属配合物包括金属化的非对称双(唑)盐。形成非对称CCC-NHC金属配合物的方法包括将二卤代苯与第一唑烷反应，形成一(唑)苯，将一(唑)苯与第二唑烷反应，形成非对称双(唑)苯，烷基化非对称双(唑)苯形成非对称双(唑)盐，金属化非对称双(唑)盐形成非对称CCC-NHC金属配合物。还提供了双配体CCC-NHC金属配合物和非对称双金属配合物。
• Bis(pyrrol-2-yl)arylenes from the Tandem Bidirectional Addition of Vinyl Grignard Reagent to Aryl Diesters
  作者：Karl A. Hansford、Sergio Andres Perez Guarin、W. G. Skene、William D. Lubell

  DOI：10.1021/jo0510888

  日期：2005.9.1

  A practical three-step synthesis of bis(pyrrol-2-yl)arylenes has been accomplished, featuring a copper-catalyzed tandem bidirectional addition of vinylmagnesium bromide to aryldicarboxylates. Spectroscopic and cyclic voltammetric analyses revealed the influence of the central aromatic core and pyrrole substitution pattern on the electrochemical properties of these comonomers.

  已经完成了实用的三步合成双（吡咯-2-基）亚芳基的方法，其特征在于铜催化的乙烯基溴化镁的串联双向双向加成到芳基二羧酸酯上。光谱和循环伏安分析揭示了中心芳族核和吡咯取代方式对这些共聚单体的电化学性能的影响。
• Unsymmetric CCC-NHC pincer metal complexes and methods of use thereof
  申请人：Mississippi State University

  公开号：US10927099B2

  公开（公告）日：2021-02-23

  Provided herein are unsymmetrical bis(azolium) salts, unsymmetrical CCC-NHC metal complexes, and methods of forming the same. The unsymmetrical bis(azolium) salts include a central aryl ring that is substituted with two heterocyclic rings in an ortho, meta, or para fashion. The unsymmetrical CCC-NHC metal complexes include metalated unsymmetrical bis(azolium) salts. The method of forming the unsymmetrical CCC-NHC metal complexes includes reacting a dihalogenated benzene with a first azole to form a mono(azole)benzene, reacting the mono(azole)benzene with a second azole to form an unsymmetrical bis(azole)benzene, alkylating the unsymmetrical bis(azole)benzene to form an unsymmetrical bis(azolium) salt, and metalating the unsymmetrical bis(azolium) salt to form the unsymmetrical CCC-NHC metal complex. Also provided are a bis-ligated CCC-NHC metal complex and an unsymmetrical bimetallic complex.

  本文提供了非对称的双（偶氮）盐、非对称的 CCC-NHC 金属配合物以及形成它们的方法。非对称双（偶氮）盐包括一个被两个杂环以正、偏或对位方式取代的芳基中心环。不对称 CCC-NHC 金属配合物包括金属化的不对称双唑盐。形成不对称 CCC-NHC 金属络合物的方法包括：使二卤化苯与第一唑反应生成单（唑）苯，使单（唑）苯与第二唑反应生成不对称双（唑）苯、将不对称的双(唑)苯烷基化，形成不对称的双(唑)盐，并将不对称的双(唑)盐金属化，形成不对称的 CCC-NHC 金属络合物。此外，还提供了一种双配位 CCC-NHC 金属络合物和一种非对称双金属络合物。
• A simple way to sequentially connected polycycles containing terminal pyrrole rings: synthesis of possible precursors of materials for nonlinear optics
  作者：Francesco Lucchesini

  DOI：10.1016/s0040-4020(01)92285-9

  日期：1992.11

  the readily available 1,3-dioxolane-2-propanal allows the transformation of aromatic and heteroaromatic mono and dilithioderivatives into polycycles containing one or two pyrrole rings. Organolithiums bearing electron acceptor groups can be also employed affording possible precursors of materials for nonlinear optics.
• UNSYMMETRICAL SALTS, CCC-NHC PINCER METAL COMPLEXES, AND METHODS OF MAKING THE SAME
  申请人：Mississippi State University

  公开号：EP3600656A1

  公开（公告）日：2020-02-05