N-methyl-2,6-dipyridin-2-ylpyridin-4-amine | 878283-35-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-methyl-2,6-dipyridin-2-ylpyridin-4-amine
• CAS: 878283-35-3
• 化学式: C₁₆H₁₄N₄
• 分子量: 262.314
• InChiKey: DNBNHHNGWMTCDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methyl-2,6-dipyridin-2-ylpyridin-4-amine 、 zinc dibromide 以 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  π Donation and Its Effects on the Excited-State Lifetimes of Luminescent Platinum(II) Terpyridine Complexes in Solution

  摘要：

  Introducing electron-donating groups extends the excited-state lifetimes of platinum(II) terpyridine complexes in fluid solution. Such systems are of interest for a variety of applications, viz., as DNA binding agents or as components in luminescence-based devices, especially sensors. The complexes investigated here are of the form [Pt(4'-X-T)Y], where 4'-X-T denotes a 4' substituted 2,2':6',2 ''-terpyridine ligand and Y denotes the coligand. The pi-donating abilities of X and Y increase systematically in the orders NHMe < -NMe2 < (pyrrolidin-l-yl) and -CN < -Cl < -CCPh, respectively. The results presented include crystal structures of two new 4'-NHMe-T complexes of platinum, as well as absorption, emission, and excited-state Lifetime data for nine complexes. Excited-state lifetimes obtained in deoxygenated dichloromethane vary by a factor of 100, ranging from 24 mu s for [Pt(4'-pyrr-T)CN](+) to 0.24 mu s for [Pt(4'-ma-T)Cl]+, where ma-T denotes 4'(methylamino)-2,2':6',2 ''-terpyridine and pyrr-T denotes 4'-(pyrrolidin-l-y)-2,2':6',2 ''-terpyridine. Analysis of experimental and computational results shows that introducing a simple amine group on the terpyridine and/or a pi-donating coligand engenders the emitting state with intraligand charge transfer (ILCT) and/or ligand ligand charge transfer (LLCT) character. The excited state lifetime increases when the change in orbital parentage lowers the emission energy, suppresses quenching via d-d states, and encourages delocalization of the excitation onto the ligand(s). At some point, however, the energy is low enough that direct vibronic coupling to the ground-state surface becomes important, and the lifetime begins to decrease again.

  DOI：

  10.1021/ic4004643
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 N-methyl-2,6-dipyridin-2-ylpyridin-4-amine
  参考文献：
  名称：

  π Donation and Its Effects on the Excited-State Lifetimes of Luminescent Platinum(II) Terpyridine Complexes in Solution

  摘要：

  Introducing electron-donating groups extends the excited-state lifetimes of platinum(II) terpyridine complexes in fluid solution. Such systems are of interest for a variety of applications, viz., as DNA binding agents or as components in luminescence-based devices, especially sensors. The complexes investigated here are of the form [Pt(4'-X-T)Y], where 4'-X-T denotes a 4' substituted 2,2':6',2 ''-terpyridine ligand and Y denotes the coligand. The pi-donating abilities of X and Y increase systematically in the orders NHMe < -NMe2 < (pyrrolidin-l-yl) and -CN < -Cl < -CCPh, respectively. The results presented include crystal structures of two new 4'-NHMe-T complexes of platinum, as well as absorption, emission, and excited-state Lifetime data for nine complexes. Excited-state lifetimes obtained in deoxygenated dichloromethane vary by a factor of 100, ranging from 24 mu s for [Pt(4'-pyrr-T)CN](+) to 0.24 mu s for [Pt(4'-ma-T)Cl]+, where ma-T denotes 4'(methylamino)-2,2':6',2 ''-terpyridine and pyrr-T denotes 4'-(pyrrolidin-l-y)-2,2':6',2 ''-terpyridine. Analysis of experimental and computational results shows that introducing a simple amine group on the terpyridine and/or a pi-donating coligand engenders the emitting state with intraligand charge transfer (ILCT) and/or ligand ligand charge transfer (LLCT) character. The excited state lifetime increases when the change in orbital parentage lowers the emission energy, suppresses quenching via d-d states, and encourages delocalization of the excitation onto the ligand(s). At some point, however, the energy is low enough that direct vibronic coupling to the ground-state surface becomes important, and the lifetime begins to decrease again.

  DOI：

  10.1021/ic4004643

文献信息

• Metal Complex, Luminescent Solid, Organic El Element and Organic El Display
  申请人：Sotoyama Wataru

  公开号：US20070296329A1

  公开（公告）日：2007-12-27

  The present invention aims to provide metal complexes, suited to luminescent materials or color transfer materials in organic EL elements or lighting systems. The metal complexes according to the present invention comprise a metal atom, a tridentate ligand, and one of monodentate ligands and halogen atoms, wherein the tridentate ligand binds to the metal atom at three sites through three nitrogen atoms of a first nitrogen atom, a second nitrogen atom and a third nitrogen atom, and the one of monodentate ligands and halogen atoms binds to the metal atom. The metal complexes are preferably expressed by General Formula (1) shown below.
• π Donation and Its Effects on the Excited-State Lifetimes of Luminescent Platinum(II) Terpyridine Complexes in Solution
  作者：Lauren M. Hight、Meaghan C. McGuire、Yu Zhang、Matthew A. Bork、Phillip E. Fanwick、Adam Wasserman、David R. McMillin

  DOI：10.1021/ic4004643

  日期：2013.8.5

  Introducing electron-donating groups extends the excited-state lifetimes of platinum(II) terpyridine complexes in fluid solution. Such systems are of interest for a variety of applications, viz., as DNA binding agents or as components in luminescence-based devices, especially sensors. The complexes investigated here are of the form [Pt(4'-X-T)Y], where 4'-X-T denotes a 4' substituted 2,2':6',2 ''-terpyridine ligand and Y denotes the coligand. The pi-donating abilities of X and Y increase systematically in the orders NHMe < -NMe2 < (pyrrolidin-l-yl) and -CN < -Cl < -CCPh, respectively. The results presented include crystal structures of two new 4'-NHMe-T complexes of platinum, as well as absorption, emission, and excited-state Lifetime data for nine complexes. Excited-state lifetimes obtained in deoxygenated dichloromethane vary by a factor of 100, ranging from 24 mu s for [Pt(4'-pyrr-T)CN](+) to 0.24 mu s for [Pt(4'-ma-T)Cl]+, where ma-T denotes 4'(methylamino)-2,2':6',2 ''-terpyridine and pyrr-T denotes 4'-(pyrrolidin-l-y)-2,2':6',2 ''-terpyridine. Analysis of experimental and computational results shows that introducing a simple amine group on the terpyridine and/or a pi-donating coligand engenders the emitting state with intraligand charge transfer (ILCT) and/or ligand ligand charge transfer (LLCT) character. The excited state lifetime increases when the change in orbital parentage lowers the emission energy, suppresses quenching via d-d states, and encourages delocalization of the excitation onto the ligand(s). At some point, however, the energy is low enough that direct vibronic coupling to the ground-state surface becomes important, and the lifetime begins to decrease again.