4,15-bisphenylethynyl[2.2]paracyclophane | 1019983-05-1

• 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: 4,15-bisphenylethynyl[2.2]paracyclophane
• 英文别名: 4,13-bis(phenylethynyl)[2.2]paracyclophane；5,12-Bis(2-phenylethynyl)tricyclo[8.2.2.24,7]hexadeca-1(12),4,6,10,13,15-hexaene
• CAS: 1019983-05-1
• 化学式: C₃₂H₂₄
• 分子量: 408.543
• InChiKey: MLBWJOGBGDSNPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  4,15-bisphenylethynyl[2.2]paracyclophane 在 potassium permanganate 、 四乙基溴化铵 、 ammonium acetate 、 碳酸氢钠 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 64.0h， 生成 pseudogem-4,15-bis(2,5-diphenyl-1H-imidazol-4-yl)[2.2]paracyclophane
  参考文献：
  名称：

  Enhancing the Versatility and Functionality of Fast Photochromic Bridged Imidazole Dimers by Flipping Imidazole Rings

  摘要：

  The widely tunable optical properties and the visible sensitivity have been required for fast photochromic molecules whose coloration decoloration cycle completes in mu s to ms time scale not only for practical applications such as full-color holographic displays but also for fundamental researches in biochemistry. However, the so far developed [2.2]paracyclophane-bridged imidazole dimers, which are one of the best candidates for fast photochromic molecules, have their weaknesses for these requirements. Herein, we overcome the issues with sustaining fast photochromism and high durability by flipping the two imidazole rings (the head-to-tail and tail-to-tail forms). The alteration in the relative configuration of the imidazole rings suppresses the broad absorption band resulting from the radical-radical interaction. The substitution to the 2-position of the imidazole ring of the tail-to-tail form gives the drastic changes in the steady-state and the transient absorption spectra. The pyrene-substituted tail-to-tail form demonstrates that the transient absorption spectrum is featured by the inherent spectrum of the imidazolyl radical. This molecular framework is easy to functionalize fast photochromic molecules such as sensitizations to the red light, chirality, and biological tagging, and therefore it is versatile for various fast photochromic applications.

  DOI：

  10.1021/ja501028v
• 作为产物：
  描述：

  碘苯 、 4,15-diethynyl[2.2]paracyclophane 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 反应 30.0h， 生成 4,15-bisphenylethynyl[2.2]paracyclophane
  参考文献：
  名称：

  基于平面手性伪间-[2.2]对环芳烃的纳米碳大环

  摘要：

  平面手性伪间-[2.2]对环芳烷与环对亚苯基骨架的结合产生了项链状手性大环化合物，具有独特的光物理性质，荧光量子产率高达82%。此外，与尺寸相关的手性具有中等大| 克拉姆| _ 观察到源自[2.2]对环芳烷的平面手性的CPL亮度B CPL值。

  DOI：

  10.1002/chem.202103832

文献信息

• Reduction of Pseudo-geminal Bis(ethynyl)-Substituted [2.2]Paracyclophanes
  作者：Lucian Birsa、Laura Sarbu、Henning Hopf、Jörg Grunenberg

  DOI：10.1055/s-0034-1378935

  日期：——

  The reduction of pseudo-geminal bis(ethynyl)-substituted [2.2]paracyclophanes provides compounds with new bridges. The type of bridging is substituent dependent. The (trimethylsilyl)ethynyl moiety induces the formation of a bridge with two semicyclic double bonds; less bulky substituents, like propynyl and phenylethynyl, lead to bridges with endo double bonds.

  假双（乙炔基）取代的 [2.2] 对环芳烃的还原为化合物提供了新的桥。桥接的类型取决于取代基。(三甲基甲硅烷基)乙炔基部分诱导形成具有两个半环双键的桥；体积较小的取代基，如丙炔基和苯乙炔基，会产生带有内双键的桥。
• Enhancing the Versatility and Functionality of Fast Photochromic Bridged Imidazole Dimers by Flipping Imidazole Rings
  作者：Kentaro Shima、Katsuya Mutoh、Yoichi Kobayashi、Jiro Abe

  DOI：10.1021/ja501028v

  日期：2014.3.12

  The widely tunable optical properties and the visible sensitivity have been required for fast photochromic molecules whose coloration decoloration cycle completes in mu s to ms time scale not only for practical applications such as full-color holographic displays but also for fundamental researches in biochemistry. However, the so far developed [2.2]paracyclophane-bridged imidazole dimers, which are one of the best candidates for fast photochromic molecules, have their weaknesses for these requirements. Herein, we overcome the issues with sustaining fast photochromism and high durability by flipping the two imidazole rings (the head-to-tail and tail-to-tail forms). The alteration in the relative configuration of the imidazole rings suppresses the broad absorption band resulting from the radical-radical interaction. The substitution to the 2-position of the imidazole ring of the tail-to-tail form gives the drastic changes in the steady-state and the transient absorption spectra. The pyrene-substituted tail-to-tail form demonstrates that the transient absorption spectrum is featured by the inherent spectrum of the imidazolyl radical. This molecular framework is easy to functionalize fast photochromic molecules such as sensitizations to the red light, chirality, and biological tagging, and therefore it is versatile for various fast photochromic applications.
• Nanosized Carbon Macrocycles Based on a Planar Chiral Pseudo <i>Meta</i> ‐[2.2]Paracyclophane
  作者：Jing He、Mohan Yu、Maofu Pang、Yanqing Fan、Zhe Lian、Ying Wang、Wenguang Wang、Yajun Liu、Hua Jiang

  DOI：10.1002/chem.202103832

  日期：2022.3

  The combination of planar chiral pseudo meta- [2.2]paracyclophane with cycloparaphenylenes backbone leads to necklace-shaped chiral macrocycles, which exhibit unique photophysical properties with high fluorescence quantum yield of up to 82 %. In addition, size-dependent chiroptical properties with moderately large |glum| and CPL brightness BCPL value originating from the planar chirality of [2.2]paracyclophane

  平面手性伪间-[2.2]对环芳烷与环对亚苯基骨架的结合产生了项链状手性大环化合物，具有独特的光物理性质，荧光量子产率高达82%。此外，与尺寸相关的手性具有中等大| 克拉姆| _ 观察到源自[2.2]对环芳烷的平面手性的CPL亮度B CPL值。