N-(2-pyridylmethylene)-1-pyrenylamine | 1394257-41-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: N-(2-pyridylmethylene)-1-pyrenylamine
• 英文别名: N-pyren-1-yl-1-pyridin-2-ylmethanimine
• CAS: 1394257-41-0
• 化学式: C₂₂H₁₄N₂
• 分子量: 306.367
• InChiKey: MGFKIGSNSAICMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  五羰基氯铼(I) 、 N-(2-pyridylmethylene)-1-pyrenylamine 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 以85%的产率得到
  参考文献：
  名称：

  Coordination entities of a pyrene-based iminopyridine ligand: Structural and photophysical properties

  摘要：

  A pyrene-based iminopyridine ligand L has been prepared and displays the absorption and emission properties expected for pyrene-based derivatives in solution. Ligand L, as well as two neutral and, one monocationic coordination entities, respectively formulated as [ZnLCl2] 1, [ReLCl(CO)(3)] 3 and [CuL2] (BF4) 2, have been crystallized and analyzed by single crystal X-ray diffraction analysis. The corresponding crystal structures indicate the formation of supramolecular architectures generated by offset pi...pi stacking between pyrene fragments and strong C-H center dot center dot center dot pi is interactions in coordination entity 1. For the cationic coordination entity 2, the crystal packing reveals the presence of C-H center dot center dot center dot F and C-H center dot center dot center dot pi interactions and numerous C-H center dot center dot center dot pi contacts interconnecting the molecules into a 3D network. As for coordination entity 3, hydrogen bonding and pi center dot center dot center dot pi stacking link the molecules in a three dimensional manner. Zinc(II) and copper(I) coordination entities have also been studied through isothermal titration calorimetry, which indicate a strong binding and a different stoichiometry for both coordination entities. Photophysical studies of the ligand and corresponding coordination entities show a monomer type pyrene emission and a higher fluorescence quantum yield for the zinc coordination entity 1 as compared with copper 2 and rhenium 3 coordination entities. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2017.07.001
• 作为产物：
  描述：

  吡啶-2-甲醛 、 1-氨基芘 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以51%的产率得到N-(2-pyridylmethylene)-1-pyrenylamine
  参考文献：
  名称：

  钯催化CO /乙烯基芳烃聚酮合成中立体化学控制的前所未有的共聚单体依赖性

  摘要：

  使用两个pyr标记的亚氨基吡啶（NN '）合成中性和单阳离子钯（II）配合物[Pd（Me）Cl（NN '）]和[Pd（Me）（MeCN）（N） N'）] [PF 6 ]。单阳离子络合物在CO /乙烯基芳烃共聚反应中生成活性催化剂，从而导致聚酮的收率和分子量强烈依赖于N-N'，而酮亚胺催化剂的生产效率比醛亚胺对应物高出一个数量级。发现用醛亚胺催化剂合成的聚酮的立体化学取决于乙烯基共聚单体：主要获得苯乙烯的间同立构共聚物，主要生产4-甲基苯乙烯的全同立构共聚物，形成4-甲基苯乙烯的无规立构大分子叔丁基苯乙烯。统计分析表明，立体化学的控制从对4-甲基苯乙烯的对映选择性位点控制变为对苯乙烯的链端和对映选择性位点控制的组合。

  DOI：

  10.1002/cctc.201500498

文献信息

• Unprecedented Comonomer Dependence of the Stereochemistry Control in Pd-Catalyzed CO/Vinyl Arene Polyketone Synthesis
  作者：Giovanni Canil、Vera Rosar、Silvia Dalla Marta、Simona Bronco、Francesco Fini、Carla Carfagna、Jérôme Durand、Barbara Milani

  DOI：10.1002/cctc.201500498

  日期：2015.7.13

  complexes generated active catalysts in the CO/vinyl arene copolymerization, leading to polyketones with yields and molecular weight strongly dependent on N‐N′, with the ketimine catalysts one order of magnitude more productive than the aldimine counterpart. The stereochemistry of polyketones synthesized with the aldimine catalyst was found to be dependent on the vinyl comonomer: prevailingly syndiotactic copolymers

  使用两个pyr标记的亚氨基吡啶（NN '）合成中性和单阳离子钯（II）配合物[Pd（Me）Cl（NN '）]和[Pd（Me）（MeCN）（N） N'）] [PF 6 ]。单阳离子络合物在CO /乙烯基芳烃共聚反应中生成活性催化剂，从而导致聚酮的收率和分子量强烈依赖于N-N'，而酮亚胺催化剂的生产效率比醛亚胺对应物高出一个数量级。发现用醛亚胺催化剂合成的聚酮的立体化学取决于乙烯基共聚单体：主要获得苯乙烯的间同立构共聚物，主要生产4-甲基苯乙烯的全同立构共聚物，形成4-甲基苯乙烯的无规立构大分子叔丁基苯乙烯。统计分析表明，立体化学的控制从对4-甲基苯乙烯的对映选择性位点控制变为对苯乙烯的链端和对映选择性位点控制的组合。
• Atropisomerism in a thermally switchable, cyclometallated iridium complex
  作者：Ashlee J. Howarth、David L. Davies、Francesco Lelj、Michael O. Wolf、Brian O. Patrick

  DOI：10.1039/c2dt31120h

  日期：——

  Two stable diastereomeric atropisomers of a cyclometallated iridium complex containing a pyrene functionalized pyridine imine ligand have been isolated. These are the first fully characterized examples of metal containing atropisomers in which the rotational axis is not between two chelating atoms. The atropisomers can be converted thermally via a rocking motion of the pyrene moiety.

  已分离出含有芘官能化吡啶亚胺配体的环金属化铱配合物的两种稳定的非对映异构体阻转异构体。这些是第一个完全表征的含金属阻转异构体的例子，其中旋转轴不在两个螯合原子之间。阻转异构体可以通过芘部分的摇摆运动进行热转化。
• Coordination entities of a pyrene-based iminopyridine ligand: Structural and photophysical properties
  作者：Awatef Ayadi、Diana G. Branzea、Magali Allain、David Canevet、Haluk Dinçalp、Abdelkrim El-Ghayoury

  DOI：10.1016/j.poly.2017.07.001

  日期：2017.10

  A pyrene-based iminopyridine ligand L has been prepared and displays the absorption and emission properties expected for pyrene-based derivatives in solution. Ligand L, as well as two neutral and, one monocationic coordination entities, respectively formulated as [ZnLCl2] 1, [ReLCl(CO)(3)] 3 and [CuL2] (BF4) 2, have been crystallized and analyzed by single crystal X-ray diffraction analysis. The corresponding crystal structures indicate the formation of supramolecular architectures generated by offset pi...pi stacking between pyrene fragments and strong C-H center dot center dot center dot pi is interactions in coordination entity 1. For the cationic coordination entity 2, the crystal packing reveals the presence of C-H center dot center dot center dot F and C-H center dot center dot center dot pi interactions and numerous C-H center dot center dot center dot pi contacts interconnecting the molecules into a 3D network. As for coordination entity 3, hydrogen bonding and pi center dot center dot center dot pi stacking link the molecules in a three dimensional manner. Zinc(II) and copper(I) coordination entities have also been studied through isothermal titration calorimetry, which indicate a strong binding and a different stoichiometry for both coordination entities. Photophysical studies of the ligand and corresponding coordination entities show a monomer type pyrene emission and a higher fluorescence quantum yield for the zinc coordination entity 1 as compared with copper 2 and rhenium 3 coordination entities. (C) 2017 Elsevier Ltd. All rights reserved.