((4-(3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-phenylthiophen-3-yl)cyclopent-1-en-1-yl)-5-methylthiophen-2-yl)ethynyl)trimethylsilane | 1093373-55-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: ((4-(3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-phenylthiophen-3-yl)cyclopent-1-en-1-yl)-5-methylthiophen-2-yl)ethynyl)trimethylsilane
• 英文别名: 3-[3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-phenyl-3-thienyl)-1-cyclopenten-1-yl]-2-methyl-5-trimethylsilylethynylthiophene
• CAS: 1093373-55-7
• 化学式: C₂₆H₂₂F₆S₂Si
• 分子量: 540.669
• InChiKey: KPZFZBFNWKCRCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.15
• 重原子数：
  35.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ((4-(3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-phenylthiophen-3-yl)cyclopent-1-en-1-yl)-5-methylthiophen-2-yl)ethynyl)trimethylsilane 在 四丁基氟化铵 作用下， 生成 5-ethynyl-3-[3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-phenyl-3-thienyl)-1-cyclopenten-1-yl]-2-methylthiophene
  参考文献：
  名称：

  基于核苷的二芳基乙烯光开关：合成和光致变色性质

  摘要：

  彩色开关：合成了基于天然脱氧腺苷的二芳基乙烯光电开关。在水溶液中，一些具有良好的光致变色特性，包括在365 nm照射时颜色发生明显变化，吸收波长发生红移，以及良好的抗疲劳性，热稳定性，转化效率和碱基配对特性。

  DOI：

  10.1002/cbic.201600171
• 作为产物：
  描述：

  生成 ((4-(3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-phenylthiophen-3-yl)cyclopent-1-en-1-yl)-5-methylthiophen-2-yl)ethynyl)trimethylsilane
  参考文献：
  名称：

  Charge Transfer and Intraligand Excited State Interactions in Platinum-Sensitized Dithienylethenes

  摘要：

  The photophysical behavior for two photochromic Pt-terpyridine acetylide complexes containing pendant dithienylethenes (DTEs) bound to the metal through the alkynyl linkage is presented. Selective excitation of the Pt complex with visible light resulted in the metal-sensitized ring closing of the DTE unit. The central purpose of this study was to understand how excited state interactions govern the photophysics by correlating differences in the linkage of the two components with differences in the intramolecular energy transfer processes that occur between the Pt complex and the DTE. A series of model complexes without photochromic ligands were prepared and studied to elucidate the contributions of the triplet metal-to-ligand charge transfer and triplet intraligand states. It is demonstrated that reducing the orbital overlap of the metal-based and intraligand states by lengthening the linkage and eliminating a conjugated pathway is effective at dramatically decreasing the efficiency of intramolecular energy transfer. This is evidenced by the appearance of Pt-terpyridine based phosphorescence and a significant decrease in the observed rate of metal-sensitized ring closing of the DTE.

  DOI：

  10.1021/ic200200j

文献信息

• Second-Order NLO Switches from Molecules to Polymer Films Based on Photochromic Cyclometalated Platinum(II) Complexes
  作者：Julien Boixel、Véronique Guerchais、Hubert Le Bozec、Denis Jacquemin、Anissa Amar、Abdou Boucekkine、Alessia Colombo、Claudia Dragonetti、Daniele Marinotto、Dominique Roberto、Stefania Righetto、Roberta De Angelis

  DOI：10.1021/ja4131615

  日期：2014.4.9

  by DFT and TD-DFT calculations. These novel Pt(II) complexes were nanoorganized in polymer films which were poled, affording new materials characterized by a good second-order NLO response that can be easily switched, with an excellent NLO contrast. To the best of our knowledge, our compounds allowed designing the very first examples of switchable NLO polymer films based on metal complexes.

  新型光致变色二噻吩乙烯基铂 (II) 配合物 (C^N^N)Pt(C≡C-DTE-C6H4-D) ((C^N^N) = 4,4'-di(n-hexyl)-制备并表征了 6-苯基-2,2'-联吡啶；D = H，NMe2)。由于在合适的电磁辐射下形成了扩展的 π 共轭配体，它们优异的光致变色特性允许在溶液中光致转换其二阶非线性光学特性，如通过 EFISH 技术测量的那样。通过 DFT 和 TD-DFT 计算，可以深入了解配合物的电子结构及其激发态的性质。这些新型 Pt(II) 复合物在极化的聚合物薄膜中进行纳米组织，提供了具有良好的二阶 NLO 响应的新材料，可以轻松切换，具有出色的 NLO 对比度。据我们所知，
• Light‐Gated Rotation in a Molecular Motor Functionalized with a Dithienylethene Switch
  作者：Diederik Roke、Constantin Stuckhardt、Wojciech Danowski、Sander J. Wezenberg、Ben L. Feringa

  DOI：10.1002/anie.201802392

  日期：2018.8.13

  which a light‐driven overcrowded alkene‐based molecular rotary motor is connected to a dithienylethene photoswitch. Ring closing of the dithienylethene moiety, using an irradiation wavelength different from the wavelength applied to operate the molecular motor, results in inhibition of the rotary motion as is demonstrated by detailed 1H‐NMR and UV/Vis experiments. For the first time, a light‐gated molecular

  提出了一种多光致变色混合系统，其中光驱动的拥挤的基于烯烃的分子旋转电机连接到二噻吩乙烯光电开关。使用不同于操作分子马达的波长的照射波长，二噻吩基乙烯部分的闭环会导致旋转运动的抑制，如详细的 1 H-NMR 和 UV/Vis 实验所证明的。由此首次获得了光门控分子马达。此外，在连接二噻吩乙烯开关后，分子马达的激发波长从紫外红移到可见光区域。
• Multistate and Multicolor Photochromism through Selective Cycloreversion in Asymmetric Platinum(II) Complexes with Two Different Dithienylethene–Acetylides
  作者：Bin Li、Hui-Min Wen、Jin-Yun Wang、Lin-Xi Shi、Zhong-Ning Chen

  DOI：10.1021/acs.inorgchem.5b02175

  日期：2015.12.7

  Four asymmetric bis(dithienylethene-acetylide) platinum(II) complexes trans-Pt(PEt3)(2)(L1o)(L5o) (1oo), trans-Pt(PEt3)(2)(L2o)(L5o) (2oo), trans-Pt(PEt3)2(L3o)(L5o) (3oo), and trans-Pt(PEt3)(2)(L4o)(L5o) (4oo) with two different dithienylethene-acetylides (L1o -L5o) were designed to modulate stepwise, multistate, and multicolor photochromism by modifying ring-closure absorption wavelengths. Upon irradiation under UV light, loo converts only to 1oc without the observation of 1co and dually ring-closed species 1cc. In contrast, both mixed ring-open/closed species oc and co as well as dually ring-closed species cc are observed upon UV light irradiation of 2oo-4oo, implying that a substantial stepwise photochromic process occurs following 2oo-4oo -> 2oc-4oc/2co-4co -> 2cc-4cc. The conversion percentage of dually ring-closed species at the photostationary state (PSS) is progressively increased following 1cc (0%) -> 2cc (40%) -> 3cc (86%) -> 4cc (>95%), coinciding with the progressive red-shift of ring-closure absorption bands in free L1c (441 nm) -> L2c (510 nm) -> L3c (556 nm) -> Mc (591 nm). Particularly, compound 2 affords four states (2oo, 2co, 2oc, and 2cc) with different colors (colorless, purple, blue, and dark blue, respectively) through a selective photochemical cycloreversion process upon irradiation with appropriate wavelengths of light. Although stepwise photocyclization reactions 3oo -> 3co/3oc -> 3cc and 4oo -> 4co/4oc -> 4cc are observed, multicolor photochromism of 3oo and 400 could not be achieved because ring-closure absorption bands between L3c/L4c and L5c are significantly overlapped. The stepwise photochemical processes are well demonstrated by NMR, UV -> vis, and infrared (IR) spectroscopy and time-dependent density functional theory (TD-DFT) computational studies.