3,3'-dimethylene-2,2'-bi<1,10>phenanthroline | 158753-10-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 3,3'-dimethylene-2,2'-bi<1,10>phenanthroline
• 英文别名: 3,3'-dimethylene-2,2'-bi-1,10-phenanthroline；3,3'-dimethylene-2,2'-bi[1,10]phenanthroline；3,6,27,30-Tetrazaheptacyclo[16.12.0.02,15.04,13.05,10.020,29.023,28]triaconta-1(18),2(15),3,5(10),6,8,11,13,19,21,23(28),24,26,29-tetradecaene
• CAS: 158753-10-7
• 化学式: C₂₆H₁₆N₄
• 分子量: 384.44
• InChiKey: KZFLZUAOQLVVQY-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  698.2±50.0 °C(predicted)
• 密度：
  1.395±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tetrakis(acetonitrile)copper(I) perchlorate 、 3,3'-dimethylene-2,2'-bi<1,10>phenanthroline 以 乙腈 为溶剂， 以88%的产率得到[(Cu(3,3'-dimethylene-2,2'-bi-1,10-phenanthroline)2](ClO4)2
  参考文献：
  名称：

  Cu(I) Complexes of 3,3‘-Polymethylene Bridged Derivatives of 2,2‘-Bi-1,10-Phenanthroline

  摘要：

  A series of 3,3'-polymethylene-2,2'-bi-1,10-phenanthrolines coordinate with Cu(I) to form dinuclear complexes [(CuL)(2)](2+). As the 3,3'-bridge is lengthened from two to four carbons, the ligand becomes more twisted about the 2,2'-bond, favoring dinuclear coordination. The distance between the two copper atoms varies from 2.92 Angstrom for the dimethylene-bridged system to 3.59 Angstrom for the tetramethylene bridge. Favorable pi-stacking interactions occur between opposing ligands and promote complex formation, Competition experiments indicate that self-recognition is important and only homoleptic complexes are observed. Under equilibrium conditions, formation of the tetramethylene-bridged complex appears to be the most favored while the dimethylene-bridged system is least favored. The intensity of the long wavelength metal-ligand charge-transfer absorption band decreases as the 3,3'-bridge is shortened. Interaction between the two copper centers is evidenced by a splitting of the oxidation wave, and this splitting increases as the Cu-Cu distance is decreased.

  DOI：

  10.1021/ic0300417
• 作为产物：
  描述：

  8-胺基-7-醛基喹啉 以73%的产率得到
  参考文献：
  名称：

  Chi-Ying Hung, Tie-Lin Wang, Zhiqiang Shi, and Randolph P. Thummel, Tetrahedron, 50 (1994) N 36, S 10685-10692

  摘要：

  DOI：

文献信息

• Material for Light Emitting Device and Light Emitting Device
  申请人：Kitazawa Daisuke

  公开号：US20070267958A1

  公开（公告）日：2007-11-22

  The invention provides a light emitting device having a low driving voltage and excellent durability by a material for a light emitting device expressed by the general formula (1): where in each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 may be the same or different and is selected from hydrogen, an alkyl group, and an aryl group, A represents an n-valent aromatic hydrocarbon group, B represents an alkyl group or an aryl group, X represents carbon or nitrogen, n represents a natural number from 2 to 6, and n substituents having a phenanthroline skeleton or a benzoquinoline skeleton may be the same or different.

  本发明提供了一种具有低驱动电压和优异耐久性的发光装置，其使用的发光装置材料由通式（1）表示，其中R1、R2、R3、R4、R5和R6中的每一个可以相同也可以不同，并且被选择为氢、烷基或芳基，A代表n价芳香族碳氢化合物基团，B代表烷基或芳基，X代表碳或氮，n代表从2到6的自然数，n个具有菲咯啉骨架或苯并喹啉骨架的取代基可以相同也可以不同。
• A Friedländer approach to novel 1,10-phenanthrolines and their use as ligands for Ru(II) and Cu(I)
  作者：Hung Chi-Ying、Wang Tie-Lin、Shi Zhiqiang、Randolph P. Thummel

  DOI：10.1016/s0040-4020(01)89260-7

  日期：1994.1
• Eu(III) Complexes of Tetradentate Ligands Related to 2,9-Di(pyrid-2′-yl)-1,10-phenanthroline and 2,2′-Bi-1,10-phenanthroline
  作者：Ruifa Zong、Gang Zhang、Svetlana V. Eliseeva、Jean-Claude G. Bünzli、Randolph P. Thummel

  DOI：10.1021/ic100338t

  日期：2010.5.17

  A series of six tetradentate polypyridine-type ligands (L) have been used to prepare the corresponding Eu(III) complexes [Eu(L)(2)(S)(n+) (n = 2, 3) where S = H2O or CF3SO3-. Two of the ligands, 2,9-di(pyrid-2'-yl)-1,10-phenanthroline (4) and its dipyridophenazine analogue (6) are symmetrical around a central phenanthroline ring. The other four ligands are 2,2'-bi-1,10-phenanthroline and its 3,3'-di-, tri-, and tetramethylene-bridged analogues (5a-d) whose conformations are governed by the length of the polymethylene bridge. H-1 NMR and X-ray analysis indicate that all of the complexes have a C-2v symmetry. The biphenanthroline series shows a strong correlation of the conjugation between the two halves of the ligand, as governed by the bridge, with the absorption and emission properties of the Eu(III) complex. The complex having the most distorted, tetramethylene-bridged ligand exhibits a weak, high energy pi-pi* absorption and low sensitization efficiency. The luminescence decays are monoexponential for complexes of 4 and either monoexponential or biexponential for the complexes of 5 depending on its solution concentration and the length of the bridge. The complexes of 4 exhibit much longer lifetime, higher overall quantum yield, and higher sensitization efficiency than complexes of 5 while the complex of 6 emits very weakly. The Eu(D-5(0)) lifetime for [Eu(4)(2)(H2O)](ClO4)(3) is shorter than for [Eu(4)(2)(CF3SO3)](CF3SO3)(2), reflecting the effect of the coordinated water. The complexes are examined for stability in the presence of water and found to retain most of their luminescent properties even in the presence of a large excess of water.
• US8114529B2
  申请人：——

  公开号：US8114529B2

  公开（公告）日：2012-02-14
• Cu(I) Complexes of 3,3‘-Polymethylene Bridged Derivatives of 2,2‘-Bi-1,10-Phenanthroline
  作者：Elvira C. Riesgo、Yi-Zhen Hu、Randolph P. Thummel

  DOI：10.1021/ic0300417

  日期：2003.10.1

  A series of 3,3'-polymethylene-2,2'-bi-1,10-phenanthrolines coordinate with Cu(I) to form dinuclear complexes [(CuL)(2)](2+). As the 3,3'-bridge is lengthened from two to four carbons, the ligand becomes more twisted about the 2,2'-bond, favoring dinuclear coordination. The distance between the two copper atoms varies from 2.92 Angstrom for the dimethylene-bridged system to 3.59 Angstrom for the tetramethylene bridge. Favorable pi-stacking interactions occur between opposing ligands and promote complex formation, Competition experiments indicate that self-recognition is important and only homoleptic complexes are observed. Under equilibrium conditions, formation of the tetramethylene-bridged complex appears to be the most favored while the dimethylene-bridged system is least favored. The intensity of the long wavelength metal-ligand charge-transfer absorption band decreases as the 3,3'-bridge is shortened. Interaction between the two copper centers is evidenced by a splitting of the oxidation wave, and this splitting increases as the Cu-Cu distance is decreased.