1,2-bis-[5'-(4''-cyanophenyl)-2'-methylthien-3'-yl]perfluorocyclopentene | 224440-78-2

• 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: 1,2-bis-[5'-(4''-cyanophenyl)-2'-methylthien-3'-yl]perfluorocyclopentene
• 英文别名: 1,2-bis-[2′-methyl-5′-(4″-cyanophenyl)-3′-thienyl]perfluorocyolopentene；1,2-Bis[2-methyl-5-(4-cyanophenyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopentene；4-[4-[2-[5-(4-cyanophenyl)-2-methylthiophen-3-yl]-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-5-methylthiophen-2-yl]benzonitrile
• CAS: 224440-78-2
• 化学式: C₂₉H₁₆F₆N₂S₂
• 分子量: 570.582
• InChiKey: MEFRDHTVXZSSIM-UHFFFAOYSA-N

物化性质

• 熔点：
  189-191 °C
• 沸点：
  630.2±55.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  39
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,2-bis-[5'-(4''-cyanophenyl)-2'-methylthien-3'-yl]perfluorocyclopentene 生成 4-[14-(4-Cyanophenyl)-8,8,9,9,10,10-hexafluoro-1,2-dimethyl-3,15-dithiatetracyclo[10.3.0.02,6.07,11]pentadeca-4,6,11,13-tetraen-4-yl]benzonitrile
  参考文献：
  名称：

  光致变色二芳烃中软硬取代基的相互作用

  摘要：

  合成了一系列具有不同大小和化学性质的取代基的二芳烃，表明除了一些涉及中心二芳基乙烯核心的分子间相互作用外，侧基显然在晶体堆积排列中起关键作用。与通过差示扫描量热法（DSC）获得的热数据有关的这些结构特征得到了进一步分析，并使用FT-IR光谱进行了监测，从而合理地观察了所观察到的热转变过程。范德华相互作用的作用对于推动晶体堆积形成以疏水接触面积大为特征的松散堆积排列至关重要。有趣的是，某些功能性取代基在热处理后倾向于非晶态，

  DOI：

  10.1016/j.jphotochem.2016.04.001
• 作为产物：
  描述：

  3,5-二溴-2-甲基噻吩 在 正丁基锂 、 硼酸三丁酯 作用下， 以 四氢呋喃 为溶剂， 生成 1,2-bis-[5'-(4''-cyanophenyl)-2'-methylthien-3'-yl]perfluorocyclopentene
  参考文献：
  名称：

  Light-driven coordination anions-directed regulation of chromism in three metal complexes assembled by cyano-equipped dithienylethene ligand

  摘要：

  DOI：

  10.1016/j.ica.2020.119666

文献信息

• Photochromic Properties of Perhydro- and Perfluorodithienylcyclopentene Molecular Switches
  作者：Jaap J. D. de Jong、Linda N. Lucas、Ralph Hania、Audrius Pugzlys、Richard M. Kellogg、Ben L. Feringa、Koos Duppen、Jan H. van Esch

  DOI：10.1002/ejoc.200200719

  日期：2003.5

  Various substituted phenylthienyl perhydro- and perfluorocyclopentenes have been synthesized in order to compare their spectroscopic and photochromic properties. The difference in the electron densities of the central cyclopentene moieties in the perhydrocyclopentene and perfluorocyclopentene molecular switches has only a small effect on the absorption maxima of the electronic spectra, but causes some

  为了比较它们的光谱和光致变色特性，已经合成了各种取代的苯基噻吩基全氢和全氟环戊烯。全氢环戊烯和全氟环戊烯分子开关中中心环戊烯部分的电子密度差异对电子光谱的吸收最大值只有很小的影响，但会引起取代基和溶剂致变色效应的一些细微变化。光致变色行为非常相似，两种类型的开关都结合了出色的量子产率 (0.6) 和高度的光转换 (> 0.85)。主要区别在于全氢环戊烯分子开关的光化学和热稳定性较低。得出的结论是，在大多数研究中，全氢环戊烯是全氟环戊烯的绝佳替代品，而全氟环戊烯可能更适合数据存储等应用，这些应用关键取决于抗疲劳性和热稳定性。((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)。
• Synthesis of Symmetrical and Nonsymmetrical Bisthienylcyclopentenes
  作者：György Szalóki、Jean-Luc Pozzo

  DOI：10.1002/chem.201301645

  日期：2013.8.19

  enabled them to find widespread applications in the field of photochromism. Nowadays, bisthienylcyclopentenes (BTCs) present the most popular subfamily of these compounds, which are widely used as P‐type chromophores. This minireview summarises the main strategies for the synthesis of symmetrical and nonsymmetrical BTCs. In addition, attention is drawn to desymmetrisations achieved by monosubstitutions

  双芳烃具有独特的结构特性，这使它们能够在光致变色领域中找到广泛的应用。如今，双噻吩基环戊烯（BTC）代表了这些化合物中最流行的亚家族，被广泛用作P型发色团。这份小型回顾总结了合成对称和非对称BTC的主要策略。另外，提请注意由单取代实现的脱对称，尽管它可以是非常有利的，但是它不经常使用。一些作者的最新结果对此提供了支持。
• Raman scattering and FT-IR spectroscopic studies on dithienylethene switches—towards non-destructive optical readout
  作者：Jaap J. D. de Jong、Wesley R. Browne、Martin Walko、Linda N. Lucas、Lindsay J. Barrett、John J. McGarvey、Jan H. van Esch、Ben L. Feringa

  DOI：10.1039/b603914f

  日期：——

  The non-destructive readout of photochromic memory materials based on the dithienylethene unit both by IR spectroscopy and Raman scattering is explored. A representative series of C5-substituted thienyl hexahydro- and hexafluoro-cyclopentene based photochromes was investigated to explore the effect and potential usefulness of substitution for the development of multicomponent memory materials. The effect of the deposition method on the photochemistry of solid materials containing photochromic dithienylcyclopentene switches was also explored. Photoconversion in the solid state to the closed form was found to be low when starting from the open form, but, in contrast, ring opening to the open state from the closed form was found to be complete. The effect was found to be due to inner filter rather than conformational phenomena. Characteristic vibrational bands for the central dithienyl core are assigned and a comparison made of the vibrational spectroscopic properties of the perhydro- and perfluoro switches. The data enable the determination of the photoconversion achievable in the solid state as well as some assessment of the influence of the deposition method on the photoconversion. The potential of Raman spectroscopy as a method of achieving non-destructive optical readout is demonstrated through the large differences in absolute Raman scattering intensity between the open and closed states, when monitored at wavelengths which do not result in photochemical ring opening.

  探索了基于二噻二烯单元的光变记忆材料的非破坏性读出，采用红外光谱和拉曼散射。研究了一系列典型的C5取代的噻吩六氢和六氟环戊烯基光变材料，以探讨取代效应及其在多组分记忆材料开发中的潜在应用。还研究了沉积方法对含有光变二噻二烯环戊烯开关固态材料光化学的影响。发现从开态转化为闭态的光转化率较低，而从闭态转化为开态的环开过程则是完全的。此现象被认为是由于内过滤效应而非构象现象。为中央的二噻二烯核心分配了特征振动带，并对氢化和氟化开关的振动光谱性质进行了比较。这些数据使得能够确定固态下可实现的光转化率，以及对沉积方法对光转化影响的某种评估。通过在不导致光化学环开过程的波长下监测开闭态之间绝对拉曼散射强度的巨大差异，证明了拉曼光谱作为实现非破坏性光学读出的潜力。
• Light-driven coordination anions-directed regulation of chromism in three metal complexes assembled by cyano-equipped dithienylethene ligand
  作者：Jing Han、Qing Li、Zhong Yu、Chun-yan Quan、Xiang Liu、Jia-cai Han

  DOI：10.1016/j.ica.2020.119666

  日期：2020.9
• The interplay of soft-hard substituents in photochromic diarylethenes
  作者：Rossella Castagna、Valentina Nardone、Giorgio Pariani、Emilio Parisini、Andrea Bianco

  DOI：10.1016/j.jphotochem.2016.04.001

  日期：2016.7

  A series of diarylethenes with substituents of different size and chemical nature was synthesised showing that beside some intermolecular interactions involving the central diarylethene core, lateral groups clearly play a key role in the crystal packing arrangements. These structural features were further analyzed in relation to the thermal data obtained by differential scanning calorimetry (DSC) and

  合成了一系列具有不同大小和化学性质的取代基的二芳烃，表明除了一些涉及中心二芳基乙烯核心的分子间相互作用外，侧基显然在晶体堆积排列中起关键作用。与通过差示扫描量热法（DSC）获得的热数据有关的这些结构特征得到了进一步分析，并使用FT-IR光谱进行了监测，从而合理地观察了所观察到的热转变过程。范德华相互作用的作用对于推动晶体堆积形成以疏水接触面积大为特征的松散堆积排列至关重要。有趣的是，某些功能性取代基在热处理后倾向于非晶态，