2,6-bis(pyrid-4-ylethynyl)aniline | 1381982-48-4

• 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-4-ylethynyl)aniline
• 英文别名: 2,6-Bis(2-pyridin-4-ylethynyl)aniline
• CAS: 1381982-48-4
• 化学式: C₂₀H₁₃N₃
• 分子量: 295.343
• InChiKey: YSRVHPOMIZXFJW-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：

  3,6-bis[trans-Pt(PEt3)2(NO3)2]phenanthrene 、 2,6-bis(pyrid-4-ylethynyl)aniline 以 甲醇 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Tunable Visible Light Emission of Self-Assembled Rhomboidal Metallacycles

  摘要：

  Supramolecular coordination complexes (SCCs) have been proposed for applications necessitating photon emitting properties; however, two critical characteristics, facile tunability and high emission quantum yields, have yet to be demonstrated on SCC platforms. Herein, a series of functionalized D-2h [D(2)A(2)] rhomboids (D = 2,6-bis(4-ethynylpyridine)aniline-based ligands; A = 2,9-bis[trans-Pt(PEt3)(2)NO3]phenanthrene) is described with emission wavelengths spanning the visible region (lambda(max) = 476-581 nm). Tuning was achieved by simple functional group modifications para to the aniline amine on the donor building block. Steady-state absorption and emission profiles were obtained for each system and are discussed. When the Hammett sigma(para) constants for the functional groups para to the aniline amine were plotted versus the wavenumber (cm(-1)) for the lambda(max) of the emission profile, a linear relationship was observed. By utilizing this relationship, the emission wavelength of a given rhomboid can be predetermined on the basis of the Hammett constant of the functionality employed on the donor precursor. This range of visible light emission for a suite of simple rhomboids along with the predictive nature of the wavelength of emission is unprecedented for these types of systems.

  DOI：

  10.1021/ja4079607
• 作为产物：
  描述：

  2,6-diethynylaniline 、 4-溴吡啶盐酸盐 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以23%的产率得到2,6-bis(pyrid-4-ylethynyl)aniline
  参考文献：
  名称：

  Photophysical and Computational Investigations of Bis(phosphine) Organoplatinum(II) Metallacycles

  摘要：

  A series of endohedral and exohedral amine-functionalized ligands were synthesized and used in the construction of supramolecular D-2h rhomboids and a D-6h hexagon. These supramolecular polygons were obtained via self-assembly of 120 degrees dipyridyl donors with 180 degrees or 120 degrees diplatinum precursors when combined in 1:1 ratios. Steady-state absorption and emission spectra were collected for each ligand and metallacycle. Density functional theory (DFT) and time-dependent DFT calculations were employed to probe the nature of the observed optical transitions for the rhomboids. The emissive properties of these bis(phosphine) organoplatinum metallacycles arise from ligand-centered transitions involving pi-type molecular orbitals with modest contributions from metal-based atomic orbitals. The D-2h rhomboid self-assembled from 2,6-bis(4-pyridylethynyl)aniline and a 60 degrees organoplatinum(II) acceptor has a low-energy excited state in the visible region and emits above 500 nm, properties which greatly differ from those of the parent 2,6-bis(4-pyridylethynyl)aniline ligand.

  DOI：

  10.1021/ja3036515

文献信息

• Metallacycle-Cored Supramolecular Polymers: Fluorescence Tuning by Variation of Substituents
  作者：Luonan Xu、Xi Shen、Zhixuan Zhou、Tian He、Jinjin Zhang、Huayu Qiu、Manik Lal Saha、Shouchun Yin、Peter J. Stang

  DOI：10.1021/jacs.8b10842

  日期：2018.12.12

  a yellow-emitting supramolecular polymer thin film with high quantum yield (0.22), a white-light-emitting LED was fabricated by painting the thin film onto an ultraviolet LED. This study presents an efficient approach for tuning the properties of fluorescent supramolecular polymers and the potential of the metallacycle-cored supramolecular polymers as a platform for the fabrication of light-emitting

  在此，我们提出了一种通过金属-配体配位和基于菲-21-冠-7（P21C7）的主客体相互作用相结合来制备具有可调荧光的超分子聚合物的方法。通过基于 P21C7 的 60° 二铂 (II) 受体和 120° 联吡啶供体的配位驱动自组装，制备了一系列具有不同取代基的菱形金属环。当联吡啶供体上的取代基发生变化时，金属环显示出跨越可见光区域的发射波长（λmax = 427-593 nm）。通过双铵盐和 P21C7 之间的主客体相互作用获得了金属环核超分子聚合物。超分子聚合物表现出与单个金属环类似的发射波长，并且在溶液和薄膜中具有更高的荧光效率。利用具有高量子产率（0.22）的黄光发射超分子聚合物薄膜，通过将该薄膜涂覆在紫外LED上制备了白光发射LED。这项研究提出了一种调节荧光超分子聚合物性能的有效方法，以及以金属环为核心的超分子聚合物作为制造具有良好加工性和可调性的发光材料的平台的潜力。
• 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