9,10-bis(4-pyridylethynyl)anthracene | 596130-35-7

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-bis(4-pyridylethynyl)anthracene
• 英文别名: 9,10-Bis(pyridin-4-ylethynyl)anthracene；4-[2-[10-(2-pyridin-4-ylethynyl)anthracen-9-yl]ethynyl]pyridine
• CAS: 596130-35-7
• 化学式: C₂₈H₁₆N₂
• 分子量: 380.448
• InChiKey: YRDFKGXHYKIWQV-UHFFFAOYSA-N

物化性质

• 熔点：
  233 °C (decomp)
• 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

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温、密闭保存，并确保环境干燥。

反应信息

• 作为反应物：
  描述：

  zinc(II) acetate dihydrate 、 9,10-bis(4-pyridylethynyl)anthracene 生成 [Zn(OAc)₂(9,10-bis(4-pyridylethynyl)anthracene)]_n
  参考文献：
  名称：

  Zn(II)/蒽配位聚合物在水溶液中表现出高效的光催化 Cr(VI) 还原

  摘要：

  摘要 Zn(OAc)2·2H2O 与可见光响应有机配体 9,10-双(4'-吡啶基乙炔基)-蒽 (BPEA) 反应生成 Zn(II)/蒽配位聚合物 [Zn(OAc) 2(BPEA)]n。化合物 1 具有一维 (1D) 链结构，其中双核 {Zn2(OAc)2} 核通过 BPEA 配体使用吡啶基 N 原子连接，形成一维梯状网络。所制备的化合物1显示出宽范围的可见光吸收和良好的水稳定性，这对其在光催化中的应用具有很高的要求。通过在可见光下在水溶液中将 Cr(VI) 还原为 Cr(III) 来研究 1 的光催化性能，这揭示了其在该光催化过程中的高效性和稳定性。

  DOI：

  10.1016/j.inoche.2019.01.006
• 作为产物：
  描述：

  9,10-二(三甲基硅乙炔基)蒽 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.5h， 生成 9,10-bis(4-pyridylethynyl)anthracene
  参考文献：
  名称：

  10.1002/chem.202400935

  摘要：

  AbstractAntiaromaticity is a fundamental concept in chemistry, but the study of molecular wires incorporating antiaromatic units is limited. Despite initial predictions, very few studies show that antiaromaticity has a beneficial effect on electron transport. Dibenzo[a,e]pentalene (DBP) is a stable structure that displays appreciable antiaromaticity within the five‐membered rings of the pentalene core. We have investigated derivatives of DBP furnished with pyridyl (Py) and F4‐pyridyl (PyF4) anchor groups, and compared the conductance with purely aromatic phenyl and anthracene analogues. We find that the low‐bias conductance of DBP‐Py is approximately 60 % larger than that of the anthracene analogue Anth‐Py and 250 % larger compared to the phenyl derivative Ph‐Py. This is due to a better alignment of the LUMO with the gold Fermi level, which we confirm by conductance‐voltage spectroscopy where the conductance of DBP‐Py shows the greatest voltage‐dependence. The F4‐pyridyl compounds, which have lower LUMO energies compared to the pyridyl analogues, did not, however, form detectable molecular junctions. The strongly electron‐withdrawing fluorine atoms reduce the donor capability of the nitrogen lone‐pair to the point where stable N−Au bonds no longer form.

  DOI：

  10.1002/chem.202400935

文献信息

• Design and Synthesis of New Differentiated Concurrent Mono- and Tridentate Ligands (Tectons) Based on Pyridine, Terpyridine, and Dihydrooxazole Units
  作者：Abdelaziz Jouaiti、Mir Wais Hosseini

  DOI：10.1002/hlca.200900087

  日期：2009.11

  The design, synthesis, and characterization of the 10 linear and bent acentric ligands 1–10 (tectons) based on the differentiation of two divergently disposed coordinating poles is reported. The nature of the two poles and their distance are varied by the use of different linear spacers. For these molecules, a monodentate coordinating site, i.e., a pyridine ring, and a tridentate coordinating site

  据报道，基于两个发散分布的配位极的区别，设计，合成和表征了10个线性和弯曲的无心配体1 – 10（结构）。通过使用不同的线性垫片，可以改变两个磁极的性质及其距离。对于这些分子，一个单齿配位位点，即吡啶环，和一个三齿配位位点，即在两个和六个位置带有两个硫醚基团或两个二甲基氨基单元的吡啶部分（PySMe和PyN（Me 2）2式中，将带有两个光学上纯净的二氢恶唑单元的叔吡啶或吡啶环结合在一起。
• New coordination polymer networks based on copper(<scp>ii</scp>) hexafluoroacetylacetonate and pyridine containing building blocks: synthesis and structural study
  作者：Silke Winter、Edwin Weber、Lars Eriksson、Ingeborg Csöregh

  DOI：10.1039/b604591j

  日期：——

  The interaction between copper(II) hexafluoroacetylacetonate [Cu(hfacac)2] and pyridine-containing building blocks with linear, angled and trigonal geometry (1–3) has led to isolation of different coordination polymers (A–D). These were studied by infrared spectroscopy and single-crystal X-ray diffraction methods. The copper coordination geometry in the present complexes can be described as a more or less distorted square bipyramid (or elongated octahedron). The unsaturated Cu(hfacac)2 units are connected by the aromatic spacer ligand moieties 1–3 so as to form polymeric frameworks, which are infinite either in one (A and D) or in two dimensions (C). The polymeric ropes or sheets are held together in the crystals by relatively weak intermolecular interactions, in which the protruding fluoro substituents of the metallic links play an active role. The porous compound A was also studied with respect to sensing reactions for potential analysis of selected volatile compounds. The screening shows interesting reactions of this coordination polymer, indicating a reversible response of relatively small and polar analytes such as methanol, ethanol and acetone, but not of water.

  通过六氟乙酰丙酮酸铜（II）[Cu(hfacac)2] 与具有线性、角形和三棱几何形状（1-3）的含吡啶构建模块之间的相互作用，分离出了不同的配位聚合物（A-D）。我们采用红外光谱和单晶 X 射线衍射方法对这些配位聚合物进行了研究。这些配合物中的铜配位几何形状可被描述为或多或少扭曲的正方二十面体（或拉长的八面体）。不饱和 Cu(hfacac)2 单元通过芳香族间隔配位体 1-3 连接，从而形成聚合物框架，这种框架在一维（A 和 D）或二维（C）上都是无限的。聚合物绳索或薄片通过相对较弱的分子间相互作用在晶体中固定在一起，其中金属链节突出的氟取代基发挥了积极作用。我们还研究了多孔化合物 A 的传感反应，以便对选定的挥发性化合物进行潜在分析。筛选结果表明，这种配位聚合物能产生有趣的反应，对甲醇、乙醇和丙酮等相对较小的极性分析物产生可逆反应，但对水没有反应。
• Synthesis, optical properties, crystal structures and phase behaviour of selectively fluorinated 1,4-bis(4?-pyridylethynyl)benzenes, 4-(phenylethynyl)pyridines and 9,10-bis(4?-pyridylethynyl)anthracene, and a Zn(NO3)2 coordination polymer
  作者：Tolulope M. Fasina、Jonathan C. Collings、Donocadh P. Lydon、David Albesa-Jove、Andrei S. Batsanov、Judith A. K. Howard、Paul Nguyen、Mitch Bruce、Andrew J. Scott、William Clegg、Stephen W. Watt、Christopher Viney、Todd B. Marder

  DOI：10.1039/b405128a

  日期：——

  A series of selectively fluorinated and non-fluorinated rigid rods based on the 4-pyridylethynyl group, namely 1,4-bis(4′-pyridylethynyl)benzene (1a), 1,4-bis(4′-pyridylethynyl)tetrafluorobenzene (1b), 1,4-bis(2′,3′,5′,6′-tetrafluoropyridylethynyl)benzene (1c), 1,4-bis(2′,3′,5′,6′-tetrafluoropyridylethynyl)tetrafluorobenzene (1d), 9,10-bis(4′-pyridylethynyl)anthracene (2), 4-(pentafluorophenylethynyl)pyridine (3a) and 4-(phenylethynyl)tetrafluoropyridine (3b) were prepared in good yields using Pd/Cu-catalysed Sonogashira cross-coupling reactions and/or lithium chemistry involving nucleophilic aromatic substitution. UV-Vis absorption and fluorescence spectra for 1a–d and 2 are reported. The X-ray crystal structures of 1b, 1c, 2, 3a and 3b show a variety of packing motifs, none of which involve arene–perfluoroarene stacking. The phase behaviour of 1a–1c has been studied by differential thermal analysis and transmitted polarised light microscopy. Compound 1b exhibits an ordered phase between 227.6 and 272.5 °C which is either hexatic B or crystal B. A 1 ∶ 1 complex (4) between 1b and Zn(NO3)2 has been prepared; its crystal structure consists of zig-zag polymer chains held together by hydrogen bonds.

  一系列基于 4-吡啶乙炔基的选择性氟化和非氟化硬棒，即 1,4-双(4â²-吡啶乙炔基)苯 (1a)、1、4-双（4â²-吡啶乙炔基）四氟苯（1b）、1,4-双（2â²,3â²,5â²,6â²-四氟吡啶乙炔基）苯（1c）、1,4-双（2â²,3â²,5â²、(1d)、9,10-双(4â²-吡啶乙炔基)蒽(2)、4-(五氟苯乙炔基)吡啶(3a)和 4-(苯乙炔基)四氟吡啶(3b)。报告了 1aâd 和 2 的紫外可见吸收光谱和荧光光谱。1b、1c、2、3a 和 3b 的 X 射线晶体结构显示出多种堆积模式，但都不涉及炔对氟碳化合物的堆积。通过差热分析和透射偏光显微镜研究了 1aâ1c 的相行为。化合物 1b 在 227.6 至 272.5 ° C 之间呈现有序相，该有序相为六方 B 或晶体 B。1b 与 Zn(NO3)2 之间的 1ⶠ1 复合物 (4) 已经制备完成；其晶体结构由通过氢键连接在一起的之字形聚合物链组成。
• DNA‐Triggered Enhancement of Singlet Oxygen Production by Pyridinium Alkynylanthracenes
  作者：Werner Fudickar、Marcel Bauch、Heiko Ihmels、Torsten Linker

  DOI：10.1002/chem.202101918

  日期：2021.9.24

  of 1O2 was confirmed by control experiments under anaerobic conditions, in deuterated solvents, or by addition of 1O2 quenchers. When bound to poly(dG : dC), the opposite effect was observed only for isomers 2 o and 2 m, namely the trapping reagent reacted significantly slower. Overall, we showed that pyridinium alkynylanthracenes are very useful intercalators, that exhibit an enhanced photochemical

  人们对1 O 2敏化剂一直感兴趣，其活性受其与 DNA 的相互作用选择性控制。为此，我们合成了三种异构的吡啶鎓炔基蒽2  o – p和一种用于1 O 2的水溶性捕集剂。在水中和不存在 DNA 的情况下，这些染料在电子转移过程中分解时显示出对捕获试剂的光氧化敏化的低效率。相比之下，在DNA 1 O 2的存在下，由激发的DNA 结合配体产生。2  o – p的相互作用通过热 DNA 熔解研究、UV/vis 和荧光光谱以及线性和圆二色光谱研究了 DNA 与 DNA 的关系。我们的研究揭示了一种插入式结合，其长吡啶-炔基轴的方向平行于 DNA 碱基对的主轴。在聚 (dA : dT) 存在下，所有三种异构体都显示出单线态氧的形成增强，如后者与捕集剂的反应所示。随着聚（dA : dT）中异构体2  o 的绿光照射，捕集剂的转化率提高了 >10 倍。1 O 2的形成通过在厌氧条件下、在氘化溶剂中的对照实验或通过添加1
• Metallacycles and methods of making the same
  申请人：Lu Kuang-Lieh

  公开号：US20090082574A1

  公开（公告）日：2009-03-26

  The present invention provides for novel metallacycles and processes for making the same.

  本发明提供了一种新型金属环化合物和制备方法。