1,8-bis(4-ethynylpyridyl)anthracene | 597543-09-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,8-bis(4-ethynylpyridyl)anthracene
• 英文别名: 1,8-bis(4-pyridyl)ethynylanthracene；1,8-bis(4-pyridylethynyl)anthracene；4-[2-[8-(2-Pyridin-4-ylethynyl)anthracen-1-yl]ethynyl]pyridine
• CAS: 597543-09-4
• 化学式: C₂₈H₁₆N₂
• 分子量: 380.448
• InChiKey: XYMYKKNGZZZDJO-UHFFFAOYSA-N

物化性质

• 沸点：
  654.4±35.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 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：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,8-bis(4-ethynylpyridyl)anthracene 在 hexafluorophosphate anion 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  新型水溶性大环化合物的高产率合成，用于萘的选择性识别

  摘要：

  以高收率合成了含有两个吡啶鎓部分的新型良好的水溶性大环化合物。它可以与水中含有萘或苯基单元的中性客体形成1：1的络合物。水溶性大环化合物可以选择性地包封萘，从而在多种多环芳烃上形成1：1的络合物。

  DOI：

  10.1016/j.cclet.2020.11.019
• 作为产物：
  描述：

  1,8-diethynylanthracene 、 4-溴吡啶盐酸盐 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二乙胺 作用下， 反应 48.0h， 以82%的产率得到1,8-bis(4-ethynylpyridyl)anthracene
  参考文献：
  名称：

  超分子笼的协调驱动自组装：含杂原子和互补三角棱镜

  摘要：

  报告了三个近似尺寸 1 x 4 nm 的纳米棱镜的自组装。四面体碳、硅和磷被用作这些基于配位的笼中的结构定义元素。碳基组件完成了一对纳米级互补 3-D 结构。结构的形成得到了多核 NMR、ESI FT-ICR 质谱和元素分析数据的支持。

  DOI：

  10.1021/ja030209n

文献信息

• Self-assembly of metal–organic hybrid nanoscopic rectangles
  作者：Sushobhan Ghosh、Partha Sarathi Mukherjee

  DOI：10.1039/b617513a

  日期：——

  The combination of an amide containing a linear ligand (L1) and an organometallic molecular “clip” (clip-1) leads to the self-assembly of a Pt4 nanoscopic framework representing the first example of a Pt-based molecular rectangle (rectangle-1) incorporating amide functionality. A complementary approach was also followed to prepare a Pd(II)-based molecular rectangle (rectangle-2) by reaction of a donor organic rigid clip (clip-2) and trans-(PEt3)2Pd(OTf)2 as the linear metal acceptor (L2). The Pd(II)-rectangle was characterised by multinuclear NMR and ESI-mass spectroscopy.

  含有线性配体（L1）的酰胺与有机金属分子“夹子”（clip-1）的组合导致形成了一个Pt4纳米级骨架，这是首个含有酰胺功能的基于铂的分子矩形（rectangle-1）的自组装实例。通过另一种互补策略，利用供体有机刚性夹子（clip-2）和trans-(PEt3)2Pd(OTf)2作为线性金属受体（L2），也合成了基于钯（II）的分子矩形（rectangle-2）。这个钯（II）矩形通过多核NMR和ESI-质谱法进行了表征。
• Coordination self-assembly of tetranuclear Pt(<scp>ii</scp>) macrocycles with an organometallic backbone for sensing of acyclic dicarboxylic acids
  作者：Sankarasekaran Shanmugaraju、Arun Kumar Bar、Harshal Jadhav、Dohyun Moon、Partha Sarathi Mukherjee

  DOI：10.1039/c2dt31828h

  日期：——

  These macrocycles were characterized by multinuclear NMR (1H and 31P); ESI-MS spectroscopy and the molecular structures of 2a and 2b were established by single crystal X-ray diffraction analysis. These macrocycles (2a–2c) are fluorescent in nature. The amide functionalized macrocycle 2a is used as a receptor to check the binding affinity of aliphatic acyclic dicarboxylic acids. Such binding affinity

  提出了一系列四核Pt（II）大环的配位自组装，这些四环Pt（II）大环含有结合乙炔基官能团的有机金属主链。线性受体1,4-双[反式-Pt（PEt 3）2（NO 3）（乙炔基）]苯（1）与三种不同的二吡啶基供体“夹子”的1：1组合（L a a–L c ç），得到3 [2 + 2]自组装的Pt II 4个大环化合物（2A-2C）中定量的产率，分别[大号一个一个= 1,3-双（3-吡啶基）isothalamide; 大号b b = 1,3-双（3-吡啶基）乙炔基苯; L c c =1,8-双（4-吡啶基）乙炔基蒽]。这些大环的特征在于多核NMR（1 H和31 P）。通过单晶X射线衍射分析建立了ESI-MS光谱和2a和2b的分子结构。这些大环（2a–2c）本质上是荧光的。酰胺官能化的大环2a用作受体，以检查脂族无环二羧酸的结合亲和力。使用荧光和UV-Vis光谱法检查这种结合亲和力。溶液状态荧光研究表明大环2a选择性结合（K
• Self-assembly of neutral and cationic PdII organometallic molecular rectangles: synthesis, characterization and nitroaromatic sensing
  作者：Arun Kumar Bar、Sankarasekaran Shanmugaraju、Ki-Whan Chi、Partha Sarathi Mukherjee

  DOI：10.1039/c0dt01048k

  日期：——

  were fully characterized by multinuclear NMR and ESI-MS spectroscopic techniques, and in case of 1 the structure was unambiguously determined by single crystal X-ray diffraction analysis. Incorporation of Pd-ethynyl bonds helped to make the assemblies π-electron rich and fluorescent in nature. Complexes 1–2 showed quenching of fluorescence intensity in solution in presence of nitroaromatics, which are

  通过预先设计的Pd（II）配位体的配位驱动自组装，设计和合成了三个新颖的[2 + 2]自组装分子矩形1-3。1,8-二乙硫基蒽在CuCl催化剂存在下，用反式-Pd（PEt 3）2 Cl 2组装通过Pd-C键形成中性矩形1。配合物1代表通过C-Pd配位驱动的自组装获得的中性分子矩形的第一个例子。一种新的Pd 2 II有机金属积木180°咬入角1,4-双[反式- （乙炔基）的Pd（PET 3）2（NO 3）]苯（中号2通过使用Sonagashira偶联反应，以合理的产率合成了含有乙炔基官能团的）。用两个有机夹子型供体（L 2 -L 3）自组装M 2分别得到[2 + 2]个自组装分子矩形2和3 [ L 2 =1,8-双（4-吡啶乙炔基）蒽; L 3 =1,3-双（3-吡啶基）间苯二甲酰胺]。大环1-3通过多核NMR和ESI-MS光谱技术进行了充分表征，在1的情况下，其结构是通过单晶X射线衍射分析
• Constructions of 2D-Metallamacrocycles Using Half-Sandwich Ru^II₂ Precursors: Synthesis, Molecular Structures, and Self-Selection for a Single Linkage Isomer
  作者：Sankarasekaran Shanmugaraju、Arun Kumar Bar、Sachin A. Joshi、Yogesh P. Patil、Partha Sarathi Mukherjee

  DOI：10.1021/om2000019

  日期：2011.4.11

  Coordination-driven self-assembly of oxalato-bridged half-sandwich p-cymene ruthenium complex [Ru-2(mu-eta(4)-C2O4)(MeOH)(2)(eta(6)-p-cymene)(2)] (O3SCF3)(2) (1a) with several ditopic donors (L-a-L-d) in methanol affords a series of bi- and tetranuclear metallamacrocycles (2a and 3-5). Similarly, the combination of 2,5-dihydroxy-1,4-benzoquinonato (dhbq)-bridged binuclear complex [Ru-2(mu-eta(4)-C6H2O4)(MeOH)(2)(eta(6)-p-cymene)(2)](O3SCF3)(2) (1b) with a flexible bidentate amide linker (L-a) in 1:1 molar ratio gave the corresponding tetranuclear complex 2b. All the macrocycles were isolated as their triflate salts in high yields and were fully characterized by various spectroscopic techniques. Finally, the molecular structures of all the assemblies were determined unambiguously by single-crystal X-diffraction analysis. Interestingly, the combination of acceptor 1a or 1b with an unsymmetrical linear ditopic donor L-a results in a self-sorted linkage isomeric (head-to-tail) macrocycle (2a or 2b) despite the possibility of formation of two different isomeric macrocycles (head-to-head or head-to-tail) due to different connectivity of the donor. Molecular structures of the complexes 2a and 2b showed tetranuclear rectangular geometry with dimensions of 5.51 angstrom x 13.29 angstrom for 2a and 7.91 angstrom x 13.46 angstrom for 2b. In both cases, two binuclear Ru-2(II) building blocks are connected by a mu-N-(4-pyridyl)isonicotinamide donor in a head-to-tail fashion. Surprisingly, the macrocycle 2a loses one counteranion and cocrystallizes with monodeprotonated 1,3,5-trihydroxybenzene via strong intermolecular pi-pi stacking and hydrogen bonding. The tweezer complex 3 showed strong fluorescence in solution, and it showed fluorescence sensing toward nitroaromatic compounds. A fluorescence study demonstrated a marked quenching of the initial fluorescence intensity of the macrocycle 3 upon gradual addition of trinitrotoluene and exhibits significant fluorescence quenching response only for nitroaromatic compounds compared to various other aromatic compounds tested.
• Self-Assembly of Metallamacrocycles Using a Dinuclear Organometallic Acceptor: Synthesis, Characterization, and Sensing Study
  作者：Sankarasekaran Shanmugaraju、Sachin A. Joshi、Partha Sarathi Mukherjee

  DOI：10.1021/ic201745y

  日期：2011.11.21

  A dinuclear organometallic acceptor 4,4'-bis[trans-Pt(PEt3)(2)(O3SCF3)(ethynyl)]biphenyl (1) containing Pt-ethynyl functionality is synthesized. Multinuclear NMR (H-1, P-31, and C-13), infrared (IR), and electrospray ionization mass spectrometry (ESI-MS) including single-crystal X-ray diffraction analysis established the formation of 1. Equimolar treatment of acceptor 1 separately with three different "clip" type ditopic donors (L-a-L-c) yielded [2 + 2] self-assembled three metallamacrocycles 2a-2c, respectively. These macrocycles were characterized by various spectroscopic techniques, and their sizes/shapes were obtained through geometry optimization using molecular mechanics universal force field (MMUFF) simulations. Attachment of unsaturated ethynyl functionality to biphenyl building unit helped to make the macrocycles (2a-2c) pi-electron rich and thereby fluorescent in nature. Furthermore, 2c in solution has been examined to be suitable for sensing electron-deficient nitroaromatic like picric acid, which is often considered as a secondary chemical explosive. The fluorescence study of 2c showed a marked quenching of initial emission intensity upon titrating with picric acid (PA), and it exhibited the largest fluorescence quenching response with high selectivity among various other electron deficient aromatic compounds tested.