4-芘-1-基-2-吡啶-2-基吡啶 | 197852-85-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 中文名称: 4-芘-1-基-2-吡啶-2-基吡啶
• 英文名称: 4-pyren-1-yl-[2,2']bipyridinyl
• 英文别名: 4-(pyren-1-yl)-2,2′-bipyridine；4-(1''-pyrenyl)-2,2'-bipyridine；pyr-bpy；2,2'-Bipyridine, 4-(1-pyrenyl)-；4-pyren-1-yl-2-pyridin-2-ylpyridine
• CAS: 197852-85-0
• 化学式: C₂₆H₁₆N₂
• 分子量: 356.426
• InChiKey: WELJANWELQTXOT-UHFFFAOYSA-N

物化性质

• 沸点：
  559.9±40.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  6.0
• 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：

  bis(4,4'-dicarboxy-2,2'-bipyridine)dichlororuthenium(II) 、 4-芘-1-基-2-吡啶-2-基吡啶 以 sodium hydroxide 、 乙醇 、 氯仿 为溶剂， 以62%的产率得到[(dcbH2)2Ru(pyr-bpy)]Cl2
  参考文献：
  名称：

  具有耦合电子激发态的 Ru(II) 配合物中分子内能量转移和氧淬灭的 pH 控制

  摘要：

  这项工作说明了通过改变过渡金属配合物中的 pH 值来控制激发态能量转移过程。在这些系统中，具有两个羧化联吡啶配体的 Ru(II) 络合物通过两个不同的芘衍生联吡啶配体之一与芘共价连接。Ru 到羧基联吡啶 (3) MLCT 状态的能量取决于 pH 值，而芘三线态能量随溶液酸度保持不变。在 pH 0 时，(3)MLCT 态是最低能态，随着 pH 值升高和羧基-联吡啶配体相继去质子化，(3)MLCT 态的能量高于芘三重态的能量，导致观察到的发射寿命显着增加。对超快和微秒时间分辨激发态衰变的详细分析导致对激发态衰变的描述，其中涉及 (3) MLCT 和芘三重态的初始平衡，然后松弛到基态。激发态衰变的寿命由平衡的位置定义，从 pH 0 时的 2 μs 到较高 pH 时的 >10 μs，因为平衡有利于芘三重态。此外，溶解氧对激发态的猝灭表现出与激发态寿命平行的 pH 依赖性。结果说明了在开发高效发光氧

  DOI：

  10.1021/ja300866s
• 作为产物：
  描述：

  2-乙酰基吡啶 在 yttrium(III) hexafluoroacetylacetonate sodium hydroxide 、 盐酸羟胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 30.0h， 生成 4-芘-1-基-2-吡啶-2-基吡啶
  参考文献：
  名称：

  Synthesis of mono-substituted 2,2′-bipyridinesElectronic supplementary information (ESI) available: experimental details and full characterization of new compounds. See http://www.rsc.org/suppdata/cc/b2/b203595b/

  摘要：

  快速合成4-芳基-2,2'-联吡啶的方法被描述，该方法不仅有效制备了一些先前报道过的化合物并且还得到了一些新型功能化联吡啶，产率均较高。

  DOI：

  10.1039/b203595b

文献信息

• Columnar/Lamellar Packing in Cocrystals of Arylbipyridines with Diiodoperfluorobenzene
  作者：Remya Ramakrishnan、Ajith R. Mallia、M. A. Niyas、Ramarani Sethy、Mahesh Hariharan

  DOI：10.1021/acs.cgd.6b00968

  日期：2016.11.2

  π-hole···π and π–π interactions, cocrystals of nonplanar 4-arylated-2,2′-bipyridine (ArB) derivatives with 1,4-diiodo-tetrafluorobenzene (D) were generated which exhibit a promising columnar/lamellar packing arrangement. Hirshfeld surface, quantum theory of atoms in molecules, and electrostatic potential surface analyses were employed to examine the weak intermolecular interactions governing the packing

  受强方向性C–I··N非共价卤素键，π-孔···π和π–π相互作用的刺激，非平面4-芳基化2,2'-联吡啶（ArB）衍生物与1,4-的共晶体生成的二碘四氟苯（D）具有良好的柱状/片状堆积结构。利用Hirshfeld表面，分子中的原子量子理论和静电势表面分析来研究弱分子间相互作用，这些相互作用决定了ArB晶体以及与D（ArB·D）对应的共晶体的堆积排列。4-苯基-2,2'-联吡啶（PhB）和4-（萘-1-基）-2,2'-联吡啶（NaB）与D [PhB·D1，PhB·D2，（NaB）2 ·D 2.5和（NaB）3 ·D 2]展示了交替出现ArB和D单元的C–I···N定向无穷一维链。相反，C–I··N相互作用指导了在与D（PhenB·D 0.5）共聚的4-（菲基-9-基）-2,2'-联吡啶共晶体中的分子配合物的形成。通过2,2'-联吡啶和D的C–I··N相互作用的成功实施，可以将平面多芳烃中的
• The use of a monoorganotin derivative of pyrene in the palladium(0)-catalyzed synthesis of a new metal-cation complexing molecule displaying excited state charge transfer properties
  作者：Alain L. Rodriguez、Guillaume Peron、Christine Duprat、Martine Vallier、Eric Fouquet、Frédéric Fages

  DOI：10.1016/s0040-4039(97)10811-5

  日期：1998.3

  The synthesis of ligand qr-BPY, in which the 1-pyrenyl group is directly connected to the 2,2'-bipyridyl unit, is described. Preliminary fluorescence results are indicative of the formation of an emitting intramolecular charge transfer stale. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Intramolecular Electronic Energy Transfer in Ruthenium(II) Diimine Donor/Pyrene Acceptor Complexes Linked by a Single C−C Bond
  作者：Jerald A. Simon、Steven L. Curry、Russell H. Schmehl、Timothy R. Schatz、Piotr Piotrowiak、Xiaoqing Jin、Randolph P. Thummel

  DOI：10.1021/ja970069f

  日期：1997.11.1

  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.