2-(1'-pyrenyl)-1,10-phenanthroline | 197852-92-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(1'-pyrenyl)-1,10-phenanthroline
• 英文别名: 2-(Pyren-1-yl)-1,10-phenanthroline；2-(1-pyrenyl)-1,10-phananthroline；2-pyren-1-yl-1,10-phenanthroline
• CAS: 197852-92-9
• 化学式: C₂₈H₁₆N₂
• 分子量: 380.448
• InChiKey: ZYXMUDSQPAMEGC-UHFFFAOYSA-N

物化性质

• 沸点：
  628.6±45.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 顺-双(2,2'-二吡啶基)二氯化钌(II)二水合物 、 2-(1'-pyrenyl)-1,10-phenanthroline 以 乙醇 为溶剂， 以74%的产率得到
  参考文献：
  名称：

  Intramolecular Electronic Energy Transfer in Ruthenium(II) Diimine Donor/Pyrene Acceptor Complexes Linked by a Single C−C Bond

  摘要：

  The photophysical behavior of [(bpy)(2)Ru(L)](2+) complexes (L = 4-(1 ''-pyrenyl)-2,2'-bipyridine, bpy-pyr; 2-(1'-pyrenyl)-1,10-phenanthroline, phen-pyr; and 2-(2'-naphthyl)-1,10-phenanthroline, phen-nap) was investigated in solutions and frozen matrices. The conformation of the linked pyrene differs in the two complexes: The pyrene moiety is conformationally constrained to be nearly perpendicular to the phenanthroline in the phen-pyr complex while the pyrene in the bpy-pyr complex has much greater flexibility about the C-C bond linking the ligand and the pyrene. The (MLCT)-M-3 excited state of the Ru(II) diimine complex and the (3)(pi-->pi*) state of the pyrenyl substituent are nearly isoenergetic; the (MLCT)-M-3 state is the lowest energy state in the bpy-pyr complex, and the pyrene (3)(pi-->pi*) state is lower in energy for the phen-pyr complex. The bpy-pyr complex is unique in that the (MLCT)-M-3 state has a very long lived luminescence (approximately 50 mu s in degassed CH3CN). Luminescence decays for both pyrene containing complexes can be fit as double exponentials, indicating that the (MLCT)-M-3 and (3)(pi-->pi*) states are not in equilibrium. Analysis of decays obtained at several temperatures reveal that energy transfer is slower than relaxation of the (MLCT)-M-3 state but more rapid than decay of the pyrene localized (3)(pi-->pi*) state. The results also suggest that electronic coupling between the two states is weak despite the fact that the two chromophores are separated by a single covalent bond.

  DOI：

  10.1021/ja970069f
• 作为产物：
  描述：

  7-甲基-8-硝基喹啉 在 盐酸 、 氢氧化钾 、 sodium periodate 、 铁粉 作用下， 以 四氢呋喃 、 乙醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.67h， 生成 2-(1'-pyrenyl)-1,10-phenanthroline
  参考文献：
  名称：

  弗里德兰德方法学引入苯并[h]喹啉和1,10-菲咯啉亚基。

  摘要：

  已经开发了改进的8-氨基-7-喹啉甲醛的制备方法。通过先用二甲基甲酰胺二甲基乙缩醛，然后用高碘酸钠处理，可以将7-甲基-8-硝基喹啉的甲基氧化为醛。用铁还原得到氨基醛。类似的序列得到1-氨基-2-萘甲醛。喹啉衍生物与一系列乙酰基芳烃的弗里德兰德缩合反应提供了相应的2-芳基-1,10-菲咯啉。氨基醛与1,3-二乙酰基苯或2,6-二乙酰基吡啶的缩合可提供预期的Friedländer产品。对于氨基醛与1,4-二乙酰基苯，4,4'-二乙酰基联苯，1,5-二乙酰基蒽，1,2,3,4,5,6,7,8-八氢ac啶-1的反应描述了相似的化学方法8-dione和四环[6.3.0.0。（4,11）0（5，

  DOI：

  10.1021/jo952164h

文献信息

• ORGANIC ELECTROLUMINESCENCE ELEMENT
  申请人：Sony Corporation

  公开号：EP2833429A1

  公开（公告）日：2015-02-04

  An organic electroluminescence device including: an anode; one or more organic thin film layers including an emitting layer; a donor-containing layer; an acceptor-containing layer; and a light-transmissive cathode in this order, wherein the donor-containing layer comprises a compound represented by the following formula (I) or (II):

  一种有机电致发光器件，包括：一个阳极；一个或多个有机薄膜层，其中包括一个发光层；一个含供体层；一个含受体层；以及一个透光阴极，其中含供体层依次包括下式（I）或（II）所代表的化合物：
• Organic electroluminescent device
  申请人：JOLED INC

  公开号：US10573823B2

  公开（公告）日：2020-02-25

  An organic electroluminescence device including: an anode; a cathode; two or more emitting units that are disposed between the anode and the cathode, each unit having an emitting layer; and a charge-generating layer that is disposed between the emitting units, wherein the charge-generating layer includes an N layer nearer to the anode and a P layer nearer to the cathode, and the N layer includes a compound represented by the following formula (I) or (II):

  一种有机电致发光器件，包括：一个阳极；一个阴极；两个或两个以上设置在阳极和阴极之间的发光单元，每个单元都有一个发光层；以及一个设置在发光单元之间的电荷发生层，其中电荷发生层包括一个靠近阳极的 N 层和一个靠近阴极的 P 层，N 层包括下式（I）或（II）所代表的化合物：
• Cyclometalated Complexes of Ru(II) with 2-Aryl Derivatives of Quinoline and 1,10-Phenanthroline
  作者：Céline Bonnefous、Abdellatif Chouai、Randolph P. Thummel

  DOI：10.1021/ic0102844

  日期：2001.11.1

  Difficulty in cyclometalating 1-(2'-quinolinyl)pyrene and 1,3-di-(2'-quinolinyl)pyrene with Ru(H) led to a more detailed study of the cyclometalation process. A series of 2-aryl-1,10-phenanthrolines, where aryl = phenyl, 2-naphthyl, 1-anthracenyl, and 1-pyrenyl, were treated with [Ru(tPY)Cl-3] to provide either the N5Cl complex [Ru(tpy)(L)Cl](+) or this same material as a mixture with the N5C cyclometalated species [Ru(tpy)L](+). Steric effects appear to govern the ability of the ligand to attain the near planar conformation required for cyclometalation. The bridged ligand 3,1'-dimethylene-2-(2'-pyrenyl)-1,10-phenanthroline was prepared along with a quinoline analogue. The former species was found to cyclometalate at the Cl of pyrene and afford the N5Cl complex. Both the N5C (P2(1)/n (monoclinic), a = 28.1102(11), b = 8.4638(3),- c = 31.2908(12) Angstrom, Z = 8) and N5Cl (P-1 (triclinic), a = 11.7235 (10), b = 14.5306(12), c = 14.5725(12) Angstrom, Z = 2) complexes were analyzed by X-ray crystallography, and the N5Cl species evidenced a congested environment for pyrene, which is apparently stabilized by pi stacking with tpy. Similar reactions with a series of three 3,2'-bridged derivatives of 2-phenyl-1,10-phenanthroline provide both N5Cl and cyclometalated products in proportions which support the importance of,7 stacking. The electronic absorption spectra and redox potentials for these complexes evidence strong sigma donation by the cyclometalated ligand and an apparant insensitivity to the orthogonal 2-aryl group.
• ORGANIC ELECTROLUMINESCENCE DEVICE
  申请人：Idemitsu Kosan Co., Ltd.

  公开号：EP2643867B1

  公开（公告）日：2019-10-30
• ORGANIC ELECTROLUMINESCENT DEVICE
  申请人：Sony Corporation

  公开号：US20150303380A1

  公开（公告）日：2015-10-22

  An organic electroluminescence device including: an anode; a cathode; two or more emitting units that are disposed between the anode and the cathode, each unit having an emitting layer; and a charge-generating layer that is disposed between the emitting units, wherein the charge-generating layer includes an N layer nearer to the anode and a P layer nearer to the cathode, and the N layer includes a compound represented by the following formula (I) or (II):