naphtho[1,2-b][1,10]phenanthroline | 129733-35-3

• 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: naphtho[1,2-b][1,10]phenanthroline
• 英文别名: 3,2'-naphtho-(1,2-b)-1,10-phenanthroline；2,5-Diazapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1,3(12),4(9),5,7,10,13,15,17,19,21-undecaene
• CAS: 129733-35-3
• 化学式: C₂₀H₁₂N₂
• 分子量: 280.329
• InChiKey: LJFLUVXVNHXCEB-UHFFFAOYSA-N

物化性质

• 沸点：
  547.4±23.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• 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：

  naphtho[1,2-b][1,10]phenanthroline 在 copper(l) iodide 、 三乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成
  参考文献：
  名称：

  刚性 Pt(II) 配合物 [Pt(naphen)(Cl)] (Hnaphen = Naphtho[1,2-b][1,10]phenanthroline 及其衍生物的光物理研究

  摘要：

  包含刚性三齿的 Pt(II) 配合物 [Pt(naphen)(X)] (Hnaphen = 萘并[1,2- b ][1,10]菲咯啉, X = Cl 或 C≡CPh)的电化学和光物理与四氢衍生物 [Pt(thnaphen)(X)] (Hthnaphen = 5,6,8,9-tetrahydro-naphtho[1,2- b ] ) 的配合物一起研究了C^N^N配位环环萘配体[1,10]菲咯啉）和N^C^N配位络合物 [Pt(bdq)(Cl)] (Hbdq = 苯并[1,2- h :5,4- h ']二喹啉对C的可逆还原^N^N配合物，与萘酚衍生物（约-1.9 V）相比，含有萘酚配体的配合物的负电位明显更少（约-1.6 V vs. 二茂铁）。对于所有配合物在约 +0.3 V 的不可逆氧化，萘酚与萘酚相比，在电化学间隙方面产生了约 0.3 eV（1.9 对 2.2 eV）的差异。bdq 配合物完全不同，由于N^C^N配位模式在

  DOI：

  10.3390/molecules27207022
• 作为产物：
  描述：

  5,6,8,9-Tetrahydronaphtho<1.2-b><1.10>phenanthrolin 在 10% Pt/activated carbon 作用下， 以 硝基苯 为溶剂， 以61 %的产率得到naphtho[1,2-b][1,10]phenanthroline
  参考文献：
  名称：

  刚性 Pt(II) 配合物 [Pt(naphen)(Cl)] (Hnaphen = Naphtho[1,2-b][1,10]phenanthroline 及其衍生物的光物理研究

  摘要：

  包含刚性三齿的 Pt(II) 配合物 [Pt(naphen)(X)] (Hnaphen = 萘并[1,2- b ][1,10]菲咯啉, X = Cl 或 C≡CPh)的电化学和光物理与四氢衍生物 [Pt(thnaphen)(X)] (Hthnaphen = 5,6,8,9-tetrahydro-naphtho[1,2- b ] ) 的配合物一起研究了C^N^N配位环环萘配体[1,10]菲咯啉）和N^C^N配位络合物 [Pt(bdq)(Cl)] (Hbdq = 苯并[1,2- h :5,4- h ']二喹啉对C的可逆还原^N^N配合物，与萘酚衍生物（约-1.9 V）相比，含有萘酚配体的配合物的负电位明显更少（约-1.6 V vs. 二茂铁）。对于所有配合物在约 +0.3 V 的不可逆氧化，萘酚与萘酚相比，在电化学间隙方面产生了约 0.3 eV（1.9 对 2.2 eV）的差异。bdq 配合物完全不同，由于N^C^N配位模式在

  DOI：

  10.3390/molecules27207022

文献信息

• Wu, Feiyue, Inorganic Chemistry, 1999, vol. 38, # 24, p. 5620 - 5628
  作者：Wu, Feiyue

  DOI：——

  日期：——
• Crowded Cu(I) Complexes Involving Benzo[<i>h</i>]quinoline:  π-Stacking Effects and Long-Lived Excited States
  作者：Elvira C. Riesgo、Yi-Zhen Hu、Frédéric Bouvier、Randolph P. Thummel、Donald V. Scaltrito、Gerald J. Meyer

  DOI：10.1021/ic010297h

  日期：2001.7.1

  The Friedlander condensation was employed to synthesize two series of 3,3 ' -polymethylene bridged ligands, L, based on 2-(2 ' -pyridyl)-benzo[h]quinoline and 2,2 ' -bibenzo[h]quinoline (BHQ) along with the fully aromatic naphtho[1,2-b]-1,10-phenanthroline. Complexes [Cu(L)(2)](+) were prepared as their perchlorate or hexafluorophosphate salts. The solution state structures were analyzed by NMR and shielding effects reflected significant interligand pi -stacking interaction in the complexes. Solid-state structures of the complexes where L = 3,3 ' -tetramethylene-2,2 ' -bibenzo[h]quinoline or naphtho[1,2-b]-1,10-phenanthroline were determined by X-ray analysis. The tetramethylene bridged complex showed a highly distorted coordination geometry with the BHQ rings of opposing ligands pi -stacked at a interplanar distance of about 3.37 Angstrom. Complexes of the BHQ series showed a pronounced MLCT absorption maximum which shifted bathochromically from 496 to 610 nm as the 3,3 ' -bridge decreased from 4 to 2 carbons. The BHQ complexes luminesced strongly in CH2Cl2 solution and the tetramethylene-bridged system showed the longest yet recorded excited-state lifetime for a copper MLCT excited state, tau = 5.3 mus and Phi = 0.10.
• 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.
• Photophysical Study on the Rigid Pt(II) Complex [Pt(naphen)(Cl)] (Hnaphen = Naphtho[1,2-b][1,10]Phenanthroline and Derivatives
  作者：Maren Krause、Iván Maisuls、Stefan Buss、Cristian A. Strassert、Andreas Winter、Ulrich S. Schubert、Shruthi S. Nair、Benjamin Dietzek-Ivanšić、Axel Klein

  DOI：10.3390/molecules27207022

  日期：——

  The electrochemistry and photophysics of the Pt(II) complexes [Pt(naphen)(X)] (Hnaphen = naphtho[1,2-b][1,10]phenanthroline, X = Cl or C≡CPh) containing the rigid tridentate C^N^N-coordinating pericyclic naphen ligand was studied alongside the complexes of the tetrahydro-derivative [Pt(thnaphen)(X)] (Hthnaphen = 5,6,8,9-tetrahydro-naphtho[1,2-b][1,10]phenanthroline) and the N^C^N-coordinated complex

  包含刚性三齿的 Pt(II) 配合物 [Pt(naphen)(X)] (Hnaphen = 萘并[1,2- b ][1,10]菲咯啉, X = Cl 或 C≡CPh)的电化学和光物理与四氢衍生物 [Pt(thnaphen)(X)] (Hthnaphen = 5,6,8,9-tetrahydro-naphtho[1,2- b ] ) 的配合物一起研究了C^N^N配位环环萘配体[1,10]菲咯啉）和N^C^N配位络合物 [Pt(bdq)(Cl)] (Hbdq = 苯并[1,2- h :5,4- h ']二喹啉对C的可逆还原^N^N配合物，与萘酚衍生物（约-1.9 V）相比，含有萘酚配体的配合物的负电位明显更少（约-1.6 V vs. 二茂铁）。对于所有配合物在约 +0.3 V 的不可逆氧化，萘酚与萘酚相比，在电化学间隙方面产生了约 0.3 eV（1.9 对 2.2 eV）的差异。bdq 配合物完全不同，由于N^C^N配位模式在