1,5-bis(ethynyl)anthracene | 78053-57-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,5-bis(ethynyl)anthracene
• 英文别名: 1,5-bis-ethynylanthracene；1,5-diethynylanthracene
• CAS: 78053-57-3
• 化学式: C₁₈H₁₀
• 分子量: 226.277
• InChiKey: AYFSWNROBKTYPR-UHFFFAOYSA-N

物化性质

• 熔点：
  >165 °C (decomp)
• 沸点：
  415.4±18.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,5-bis(ethynyl)anthracene 在 铂(0)-1,3-二乙烯-1,1,3,3-四甲基二硅氧烷 、 三氯硅烷 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 以98%的产率得到1,5-bis[2-(trichlorosilyl)vinyl]anthracene
  参考文献：
  名称：

  Poly‐Boron, ‐Silicon, and ‐Gallium Lewis Acids by Hydrometallation of 1,5‐ and 1,8‐Dialkynylanthracenes

  摘要：

  Abstract1,5‐Dialkynylanthracenes and 1,8‐dialkynylanthracenes have been functionalised by a series of hydrometallation reactions, namely, hydrosilylation, hydroboration and hydrogallation. Nine anthracene‐based Lewis acidic compounds with a semiflexible organic framework bearing SiCl3, SiCl2Me, SiClMe2, B(C6F5)2 and GaCl2 substituents were obtained. In all cases, the substrate could be functionalised twice, and bidentate Lewis acids were obtained. By using Piers' borane [HB(C6F5)2], a fourfold‐substituted anthracene species functionalised with four extremely electronegatively substituted boron atoms could be generated in quantitative yield. All of the poly‐Lewis acids were characterised by multinuclear NMR spectroscopy and, in part, by mass spectrometry and X‐ray diffraction experiments.

  DOI：

  10.1002/ejic.201402376
• 作为产物：
  描述：

  1,5-二氯蒽 在 乙基溴化镁 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 79.25h， 生成 1,5-bis(ethynyl)anthracene
  参考文献：
  名称：

  多功能双卟啉镊子主机，用于装配非共价光敏结构：镊子的光物理特征及其与卟啉和其他客人的联系。

  摘要：

  合成了以蒽组分为先端和侧臂的双（Zn（II）-卟啉）镊子主体。单（吡啶）和双齿（4,4'-联吡啶）客体分别用作腔内单轴和双轴配位的模型。一系列具有不同取代模式和激发态能级的二吡啶基卟啉客体与镊子的缔合常数约为10（6）M（-1），表明与腔内部的络合。仅在腔体发生严重变形（使咬合张开约30％）时，才会发生这种络合。这种特性，加上通过绕单键旋转减少咬合距离的能力，使得这些卟啉镊子成为迄今为止报道的最通用的镊子之一，调整咬合距离大约在5到20埃之间。能量传递到三卟啉复合物中的游离碱客体几乎是定量的（95-98％），转移速率与以降低取向因子为特征的Forster机制一致。

  DOI：

  10.1002/chem.200500789

文献信息

• Polyalkynylanthracenes – syntheses, structures and their behaviour towards UV irradiation
  作者：Jan-Hendrik Lamm、Johanna Glatthor、Jan-Henrik Weddeling、Andreas Mix、Jasmin Chmiel、Beate Neumann、Hans-Georg Stammler、Norbert W. Mitzel

  DOI：10.1039/c4ob00735b

  日期：——

  A series of 1,5-, 1,8-, 9,10- and 1,8,10-alkynyl-substituted anthracenes have been synthesised. Amongst others, 9,10-bis[(trimethylsilyl)ethynyl]anthracene was photo-dimerised. The photodimer is thermally unstable as was investigated by VT NMR spectroscopy.

  一系列1,5-、1,8-、9,10-和1,8,10-炔基取代的蒽已经合成。其中，9,10-双[(三甲基硅基)乙炔基]蒽被光二聚化。通过VT NMR光谱研究表明，光二聚物在热稳定性方面不稳定。
• Anthracene-Bridged Binuclear Ruthenium Complexes: Electrochemical and Spectroscopic Evidence of Electronic Communication Through the π System
  作者：Neus Vilà、Yu-Wu Zhong、Jay C. Henderson、Héctor D. Abruña

  DOI：10.1021/ic900100w

  日期：2010.2.1

  spectroscopically. The anodic electrochemistry of the homobinuclear ruthenium complexes, 1−6, has been examined in three different nonaqueous solvents (ACN, DMF, and CH2Cl2). The ability of the anthracene derivatives to transmit electronic effects between the two redox units has been demonstrated by the observed splitting of the voltammetric signals ascribed to the metal centers. The electronic communication

  六环金属双核钌络合物，1 - 6，基于作为桥连配体已被合成并充分表征电化学和光谱二苯基蒽（DPA）和蒽（AN）。的homobinuclear钌络合物阳极电化学，1 - 6，已在三个不同的非水溶剂（ACN，DMF，和CH被检验2氯2）。蒽衍生物在两个氧化还原单元之间传递电子效应的能力已通过观察到归因于金属中心的伏安信号的分裂得到证明。电子通信也已通过光谱的近红外区域中存在间隔电荷转移跃迁带得到了证明，这是由于当化合价物质（Ru II / Ru III）被电化学键合时，由电桥介导的分子内电子转移过程引起的。生成的。循环伏安法测量是在溶剂和支持电解质的不同条件下进行的。ΔE的差异观察到了基于金属的阳极过程的形式势的电势分离，并取决于所使用的介质。这些差异归因于不同程度的离子配对。继而，不仅可以根据溶剂的极性和施主强度，还可以根据用作支持电解质的阴离子的配位能力来调节这种作用。
• Flash vacuum thermolysis of 1,5-Bis-(1-chloroethenyl)anthracene. The thermal conversion of cyclopent[hi]aceanthrylene into cyclopent[hi]acephenanthrylene
  作者：Martin Sarobe、Judith D. Snoeijer、Leonardus W. Jenneskens、Jan W. Zwikker、Jolanda Wesseling

  DOI：10.1016/0040-4039(95)02049-7

  日期：1995.12

  Thermolysis of 1,5-bis-(1-chloroethenyl)anthracene (6) gives cyclopent[hi]-aceanthrylene (2) which at T≥9000 °C rearranges to cyclopent[hi]acephenanthrylene (1). This conversion occurs more readily than that of the monocyclopenta-fused aceanthrylene to acephenanthrylene.

  1，5-双-（1-氯乙烯基）蒽（6）的闪蒸真空热解得到环戊基[ hi ]-乙炔（2），其在T≥9000℃下重排成环戊基[ hi ]对菲（1）。这种转化比单环戊基稠合的乙炔向对苯二甲苯的转化更容易发生。
• Synthesis of bi- and tetradentate poly-Lewis acids by hydroalumination of poly-alkynyl-anthracene derivatives
  作者：Niklas Aders、Jan-Hendrik Lamm、J. Louis Beckmann、Beate Neumann、Hans-Georg Stammler、Norbert W. Mitzel

  DOI：10.1039/d2dt02118h

  日期：——

  radiation of the monomers, were treated with the bulky aluminium hydride [(SiMe3)2HC]2AlH in hydroalumination reactions. Hydroalumination of the tetraethynyl-substituted anthracene photo-dimers (syn and anti) led to fourfold aluminium-functionalized Janus-like products with two aluminium functions on each side oriented towards the same direction. The reactions of the monomeric anthracene derivatives with [(SiMe3)2HC]2AlH

  1,5-二乙炔基蒽和1,5-双[(三甲基甲硅烷基)乙炔基]蒽的光二聚体，通过单体的紫外辐射，在氢化铝中用体积庞大的氢化铝[(SiMe 3 ) 2 HC] 2 AlH处理反应。四乙炔基取代的蒽光二聚体（顺式和反式）的氢铝化导致四重铝官能化的 Janus 样产品，每侧有两个铝官能团，朝向相同的方向。单体蒽衍生物与[(SiMe 3 ) 2 HC] 2的反应AlH 提供了半柔性的双齿路易斯酸，这是具有多个路易斯酸性功能的分子链的有趣构建块。用各种供体分子处理铝功能化的抗光二聚体，以深入了解其主客体化学。通过 X 射线衍射实验、多核 NMR 光谱和元素分析对所有聚路易斯酸及其加合物进行了表征。
• Synthesis, Characterization, and Properties of Anthracene-Bridged Bimetallic Ruthenium Vinyl Complexes [RuCl(CO)(PMe₃)₃]₂(μ-CH═CH-anthracene-CH═CH)
  作者：Ya-Ping Ou、Chuanyin Jiang、Di Wu、Jianlong Xia、Jun Yin、Shan Jin、Guang-Ao Yu、Sheng Hua Liu

  DOI：10.1021/om200622q

  日期：2011.11.14

  Four anthracene-based bimetallic ruthenium vinyl complexes, in which two ruthenium units are attached at different positions (the 9,10-, 1,5-, 2,6-, and 1,8-positions) of the anthracene moiety, have been synthesized by treating the appropriate anthracene-based ethynes with [RuHCl(CO)(PPh3)(3)]. These bimetallic complexes have been thoroughly characterized by NMR, X-ray diffraction, and elemental analysis. According to the single-crystal X-ray structures, the 2,6-disubstituted ruthenium vinyl complex has a more planar structure compared with the 9,10-disubstituted complex, possibly because it has less steric hindrance. Furthermore, we have investigated the optical electronic properties of these complexes, such as their UV/vis absorption spectra, fluorescence spectra, and electrochemical properties. The optical electronic results indicated that the 2,6-disubstituted ruthenium vinyl complex displayed the strongest fluorescence emission due to the more planar structure of its organic conjugated bridge, and the electrochemical studies showed that the two ruthenium centers displayed obvious differences in electronic communication when they are located at different positions on the anthracene unit, with the 9,10- and 1,8-disubstituted ruthenium vinyl complexes exhibiting better electronic communication and higher stability of the mixed-valence complex than the 1,5- and 2,6-disubstituted complexes.