2,6-bis(pyrid-3-ylethynyl)aniline | 1290539-07-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-bis(pyrid-3-ylethynyl)aniline
• 英文别名: 2,6-bis(pyridin-3-ylethynyl)aniline；2,6-Bis(2-pyridin-3-ylethynyl)aniline；2,6-bis(2-pyridin-3-ylethynyl)aniline
• CAS: 1290539-07-9
• 化学式: C₂₀H₁₃N₃
• 分子量: 295.343
• InChiKey: HJDXPIQJMQYNAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  palladium (II) nitrate 、 2,6-bis(pyrid-3-ylethynyl)aniline 以 氘代二甲亚砜 为溶剂， 生成
  参考文献：
  名称：

  Steric Effects Control Self-Sorting in Self-Assembled Clusters

  摘要：

  Endohedrally functionalized bis(pyridine) ligands show the ability to self-discriminate when treated with coordinating metals to form self-assembled clusters. Self-sorting between components is controlled by substitution on the interior of the complex. Tuning the size of the internal substituent allows selective heterocluster formation, determined by noncovalent and space-filling interactions. This novel method of self-sorting allows discrimination between ligands of identical geometry and donor type.

  DOI：

  10.1021/ic2001688
• 作为产物：
  描述：

  3-乙炔基吡啶 、 2,6-二溴苯胺 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 copper(l) iodide 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以49%的产率得到2,6-bis(pyrid-3-ylethynyl)aniline
  参考文献：
  名称：

  Synthesis and Properties of Metal–Ligand Complexes with Endohedral Amine Functionality

  摘要：

  A series of tetracationic M2L4 palladium-pyridyl complexes with endohedral amine functionality have been synthesized. The complexes were analyzed by NMR techniques (including Diffusion NMR and 2D NOESY), electrospray ionization (ESI) mass spectrometry, and X-ray crystallography. The solid state analysis shows a large change in crystal morphology upon introduction of the endohedral amine groups, caused by deleterious interactions between the amines and the triflate counterions from the coordination process. Combination of different ligands allows analysis of ligand exchange rates via NMR analysis, with half-lives on the order of 3 h, independent of the donor properties of the ligand. Self-sorting behavior is observed, with more electron-rich ligands being favored. The amine-containing and extended complexes are strongly fluorescent, giving quantum yields of up to 83%.

  DOI：

  10.1021/ic201092s

文献信息

• Photophysical Properties of Endohedral Amine-Functionalized Bis(phosphine) Pt(II) Complexes as Models for Emissive Metallacycles
  作者：J. Bryant Pollock、Timothy R. Cook、Gregory L. Schneider、Daniel A. Lutterman、Andrew S. Davies、Peter J. Stang

  DOI：10.1021/ic400491q

  日期：2013.8.19

  The photophysical properties of bis(phosphine) Pt(II) complexes constructed from 2,6-bis(pyrid-3-ylethynyl) aniline and 2,6-bis(pyrid-4-ylethynyl) aniline vary significantly, even though the complexes differ only in the position of the coordinating nitrogen. By capping the ligands with an aryl bis(phosphine) Pt(II) metal acceptor, the photophysical properties of the two isomeric systems were directly

  由2,6-双（吡啶-3-基乙炔基）苯胺和2,6-双（吡啶-4-基乙炔基）苯胺构成的双（膦）Pt（II）配合物的光物理性质发生显着变化，即使配合物不同仅在配氮的位置。通过用芳基双（膦）Pt（II）金属受体封端配体，直接比较了两个异构体系统的光物理性质，发现两个系统的低能吸收带和发射带之间相隔30 nm（ 1804 cm –1）和39 nm（1692 cm –1）。通过对时变密度泛函（TD-DFT）计算和激发态寿命测量的分析，可以确定HOMO中Pt–N键的性质以及辐射（krad）和非辐射（k nr）速率常数在两个系统中显着不同。由于苯胺系统中主要的非辐射衰变途径是从三重态通过系统间穿越（ISC）弛豫，因此k nr的差异可以归因于双（膦）Pt（II）封端的2,6-双（吡啶-3-基乙炔基）苯胺系统异构体之间的ISC变化。还确定可以通过官能化双（膦）Pt（II）金属中心上的芳基封端配体来改变这些封端
• Controlled Construction of Heteroleptic [Pd ₂ (L ^A ) ₂ (L ^B )(L ^C )] ⁴⁺ Cages: A Facile Approach for Site‐Selective endo‐Functionalization of Supramolecular Cavities
  作者：Yan Liu、Shou‐Heng Liao、Wen‐Tao Dai、Qixia Bai、Shuai Lu、Heng Wang、Xiaopeng Li、Zhe Zhang、Pingshan Wang、Wei Lu、Qi Zhang

  DOI：10.1002/anie.202217215

  日期：2023.2

  AbstractConstruction of supramolecular structures with internal functionalities is a promising approach to build enzyme‐like cavities. The endo‐functionalized [Pd12L24] and [Pd2L4] coordination cages represent the most successful systems in this regard. However, these systems mainly contain one type of endo‐moiety. We herein provide a solution for the controlled endo‐functionalization of [Pd2L4] cages. Site‐selective introduction of the endo‐functional group was achieved through the formation of heteroleptic [Pd2(LA)2(LB)(LC)] cages. Using two orthogonal steric control elements is the key for the selective formation of the hetero‐assemblies. We demonstrated the construction of two hetero‐cages with a single internal functional group as well as a hetero‐cage with two distinct endohedral functionalities. The endo‐functionalized hetero‐cages bound sulfonate guests with fast‐exchange dynamics. This strategy provides a new solution for the controlled endo‐functionalization of supramolecular cavities.
• Synthesis and Properties of Metal–Ligand Complexes with Endohedral Amine Functionality
  作者：Amber M. Johnson、Orly Moshe、Ana S. Gamboa、Brian W. Langloss、John F. K. Limtiaco、Cynthia K. Larive、Richard J. Hooley

  DOI：10.1021/ic201092s

  日期：2011.10.3

  A series of tetracationic M2L4 palladium-pyridyl complexes with endohedral amine functionality have been synthesized. The complexes were analyzed by NMR techniques (including Diffusion NMR and 2D NOESY), electrospray ionization (ESI) mass spectrometry, and X-ray crystallography. The solid state analysis shows a large change in crystal morphology upon introduction of the endohedral amine groups, caused by deleterious interactions between the amines and the triflate counterions from the coordination process. Combination of different ligands allows analysis of ligand exchange rates via NMR analysis, with half-lives on the order of 3 h, independent of the donor properties of the ligand. Self-sorting behavior is observed, with more electron-rich ligands being favored. The amine-containing and extended complexes are strongly fluorescent, giving quantum yields of up to 83%.
• Steric Effects Control Self-Sorting in Self-Assembled Clusters
  作者：Amber M. Johnson、Richard J. Hooley

  DOI：10.1021/ic2001688

  日期：2011.6.6

  Endohedrally functionalized bis(pyridine) ligands show the ability to self-discriminate when treated with coordinating metals to form self-assembled clusters. Self-sorting between components is controlled by substitution on the interior of the complex. Tuning the size of the internal substituent allows selective heterocluster formation, determined by noncovalent and space-filling interactions. This novel method of self-sorting allows discrimination between ligands of identical geometry and donor type.