2,3-di(2-pyridyl)-5,6-diphenylpyrazine | 127727-03-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2,3-di(2-pyridyl)-5,6-diphenylpyrazine
• 英文别名: 2,3-di-2-pyridyl-5,6-diphenylpyrazine；dpdpz；2,3-Di(2-pyridyl)-5,6-diphenylpyrazine；2,3-diphenyl-5,6-dipyridin-2-ylpyrazine
• CAS: 127727-03-1
• 化学式: C₂₆H₁₈N₄
• 分子量: 386.456
• InChiKey: BMDZFZCGZRWTHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  五羰基氯铼(I) 、 2,3-di(2-pyridyl)-5,6-diphenylpyrazine 以 甲醇 为溶剂， 以85%的产率得到[Re(CO)3Cl]2-2,3-di(2-pyridyl)-5,6-diphenylpyrazine
  参考文献：
  名称：

  Rhenium Complexes of 2,3-Di(2-pyridyl)-5,6-diphenylpyrazine: Synthesis, Characterization, and Reactivity

  摘要：

  The reaction of 2,3-di(2-pyridyl)-5,6-diphenylpyrazine (dpdpz) with Re(CO)(5)Cl in acetonitrile or toluene afforded mono-Re and bis-Re complexes [Re(CO)(3)Cl-dpdpz] and [Re(CO)(3)Cl-dpdpz-Re(CO)(3)Cl], respectively. A heterodinuclear complex [Ru(bpy)(2)-dpdpz-Re(CO)(3)Cl](PF6)(2) could be prepared by the reaction of [Re(CO)(3)Cl-dpdpz] with Ru(bpy)(2)Cl-2 or the reaction of Re(CO)(5)Cl with a previously reported mono-RU complex [Ru(bpy)(2)-dpdpz](PF6)(2) in moderate yields. Surprisingly, the reaction of [Re(CO)(3)Cl-dpdpz] or [Re(CO)(3)Cl-dpdpz-Re(CO)(3)Cl] with Ru(tpy)Cl-3 in the presence of AgOTf both afforded an asymmetric bis-Ru complex [Ru(tpy)-dpdpz-RuCl(tpy)](PF6)(2). The solid-state structures of [Re(CO)(3)Cl-dpdpz-Re(CO)(3)Cl] and [Ru(tpy)-dpdpz-RuCl(tpy)](PF6)(2) were determined by single-crystal X-ray analysis. The electrochemical, absorption, and emission properties of these compounds were studied by cyclic voltammetric and spectroscopic analyses. In addition, DFT calculations were carried out to aid in the interpretation of these experimental findings.

  DOI：

  10.1021/om201240c
• 作为产物：
  描述：

  在 氧气 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以50 mg的产率得到2,3-di(2-pyridyl)-5,6-diphenylpyrazine
  参考文献：
  名称：

  2,3-二-2-吡啶基-5,6-二苯基吡嗪单核和双核钌配合物的合成，光谱和电化学研究

  摘要：

  此处报道了一种新的桥联配体2,3-二-2-吡啶基-5,6-二苯基吡嗪（dpdpz）及其与一个或两个钌原子的络合。该配体被设计成使得其可以结合在任一A N金属物种∧ Ñ双齿方式或C ∧ Ñ ∧ Ñ三齿模式以形成一个金属环。dpdpz和（TPY）的RuCl之间的反应3 - ：（三联吡啶'6'，2''TPY = 2,2），得到Ç ∧ Ñ ∧在中等产率的N型单-和双核环金属化配合物。在另一方面，N ∧ N型单-和双核络合物noncyclometalated可从dpdpz的反应分离（BPY）2的RuCl 2（bpy = 2,2'-联吡啶）。制备了由dpdpz桥接的不对称二钌络合物，其中一个钌原子被环金属化，另一个被非环金属化。这些配合物的电子性质通过电化学和光谱技术进行探测。它们表现出多种可逆的氧化还原过程。但是，形式势和电化学能隙在很大程度上取决于钌原子的结合性质和数量。如电化学和光谱电化学研究所

  DOI：

  10.1021/ic101629w

文献信息

• Near-Infrared Absorbing and Emitting Ru^II−Pt^II Heterodimetallic Complexes of Dpdpz (Dpdpz = 2,3-Di(2-pyridyl)-5,6-diphenylpyrazine)
  作者：Si-Hai Wu、Stephen E. Burkhardt、Jiannian Yao、Yu-Wu Zhong、Héctor D. Abruña

  DOI：10.1021/ic1023696

  日期：2011.5.2

  The reaction of 2,3-di(2-pyridy1)-5,6-diphenylpyrazine (dpdpz) with K2PtCl4 in a mixture of acetonitrile and water afforded mono-Pt complex (dpdpz)PtCl2 4 in good yield, with two lateral pyridine nitrogen atoms binding to the metal center. Two types of Ru-II-Pt-II heterodimetallic complexes bridged by dpdpz, namely, [(bpy)(2)Ru(dpdpz)Pt(C CC6H4R)(2+) (7-9, R = H, NMe2, or Cl, respectively) and [(tpy)Ru(dpdpz)Pt(C CPh)](+) (12), were then designed and prepared, where bpy = 2,2'-bipyridine and tpy = 2,2';6',2 ''-terpyridine. In both cases, the platinum atom binds to dpdpz with a (CNN)-N-boolean AND-N-boolean AND tridentate mode. However, the coordination of the ruthenium atom with dpdpz could either be noncyclometalated ((NN)-N-boolean AND bidentate) or cyclometalated ((CNN)-N-boolean AND-N-boolean AND tridentate). The electronic properties of these complexes were subsequently studied and compared by spectroscopic and electrochemical analyses and theoretical calculations. These complexes exhibit substantial absorption in the visible to NIR (near-infrared) region because of mixed MLCT (metal-to-ligand-charge-tranfer) transitions from both the ruthenium and the platinum centers. Complexes 7 and 9 were found to emit NIR light with higher quantum yields than those of the mono-Ru complex [(bpy)(2)Ru(dpdpz)](2+) (5) and bis-Ru complex [(bpy)(2)Ru(dpdpz)Ru(bpy)(2)](4+) (13). However, no emission was detected from complex 8 or 12 at room temperature in acetonitrile.
• Rhenium Complexes of 2,3-Di(2-pyridyl)-5,6-diphenylpyrazine: Synthesis, Characterization, and Reactivity
  作者：Si-Hai Wu、Héctor D. Abruña、Yu-Wu Zhong

  DOI：10.1021/om201240c

  日期：2012.2.13

  The reaction of 2,3-di(2-pyridyl)-5,6-diphenylpyrazine (dpdpz) with Re(CO)(5)Cl in acetonitrile or toluene afforded mono-Re and bis-Re complexes [Re(CO)(3)Cl-dpdpz] and [Re(CO)(3)Cl-dpdpz-Re(CO)(3)Cl], respectively. A heterodinuclear complex [Ru(bpy)(2)-dpdpz-Re(CO)(3)Cl](PF6)(2) could be prepared by the reaction of [Re(CO)(3)Cl-dpdpz] with Ru(bpy)(2)Cl-2 or the reaction of Re(CO)(5)Cl with a previously reported mono-RU complex [Ru(bpy)(2)-dpdpz](PF6)(2) in moderate yields. Surprisingly, the reaction of [Re(CO)(3)Cl-dpdpz] or [Re(CO)(3)Cl-dpdpz-Re(CO)(3)Cl] with Ru(tpy)Cl-3 in the presence of AgOTf both afforded an asymmetric bis-Ru complex [Ru(tpy)-dpdpz-RuCl(tpy)](PF6)(2). The solid-state structures of [Re(CO)(3)Cl-dpdpz-Re(CO)(3)Cl] and [Ru(tpy)-dpdpz-RuCl(tpy)](PF6)(2) were determined by single-crystal X-ray analysis. The electrochemical, absorption, and emission properties of these compounds were studied by cyclic voltammetric and spectroscopic analyses. In addition, DFT calculations were carried out to aid in the interpretation of these experimental findings.
• Mononuclear and Dinuclear Ruthenium Complexes of 2,3-Di-2-pyridyl-5,6-diphenylpyrazine: Synthesis and Spectroscopic and Electrochemical Studies
  作者：Yu-Wu Zhong、Si-Hai Wu、Stephen E. Burkhardt、Chang-Jiang Yao、Héctor D. Abruña

  DOI：10.1021/ic101629w

  日期：2011.1.17

  hand, N∧N-type mono- and dinuclear noncyclometalated complexes could be isolated from the reaction of dpdpz with (bpy)2RuCl2 (bpy = 2,2′-bipyridine). An asymmetric diruthenium complex, bridged by dpdpz, was prepared with one ruthenium atom cyclometalated and another one noncyclometalated. The electronic properties of these complexes were probed by electrochemical and spectroscopic techniques. They

  此处报道了一种新的桥联配体2,3-二-2-吡啶基-5,6-二苯基吡嗪（dpdpz）及其与一个或两个钌原子的络合。该配体被设计成使得其可以结合在任一A N金属物种∧ Ñ双齿方式或C ∧ Ñ ∧ Ñ三齿模式以形成一个金属环。dpdpz和（TPY）的RuCl之间的反应3 - ：（三联吡啶'6'，2''TPY = 2,2），得到Ç ∧ Ñ ∧在中等产率的N型单-和双核环金属化配合物。在另一方面，N ∧ N型单-和双核络合物noncyclometalated可从dpdpz的反应分离（BPY）2的RuCl 2（bpy = 2,2'-联吡啶）。制备了由dpdpz桥接的不对称二钌络合物，其中一个钌原子被环金属化，另一个被非环金属化。这些配合物的电子性质通过电化学和光谱技术进行探测。它们表现出多种可逆的氧化还原过程。但是，形式势和电化学能隙在很大程度上取决于钌原子的结合性质和数量。如电化学和光谱电化学研究所