1,2-bis[2-methyl-5-(p-(N,N-dimethylamino)phenyl)-3-thienyl]perfluorocyclopentene | 676461-03-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,2-bis[2-methyl-5-(p-(N,N-dimethylamino)phenyl)-3-thienyl]perfluorocyclopentene
• 英文别名: 3,3'-(Hexafluorocyclopentene-1,2-diyl)bis[5-[4-(dimethylamino)phenyl]-2-methylthiophene]；4-[4-[2-[5-[4-(dimethylamino)phenyl]-2-methylthiophen-3-yl]-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-5-methylthiophen-2-yl]-N,N-dimethylaniline
• CAS: 676461-03-3
• 化学式: C₃₁H₂₈F₆N₂S₂
• 分子量: 606.699
• InChiKey: QEHIJXMTTCYPBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  63
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,2-bis[2-methyl-5-(p-(N,N-dimethylamino)phenyl)-3-thienyl]perfluorocyclopentene 以 乙腈 为溶剂， 生成 4-[14-[4-(dimethylamino)phenyl]-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]-N,N-dimethylaniline
  参考文献：
  名称：

  Photoelectrochromic Dithienylperfluorocyclopentene Derivatives

  摘要：

  二噻吩基全氟环戊烯衍生物，带有连接到噻吩杂环的两个碳原子上的烷基取代基，在其闭环形式中，形成新的 C-C 单键（噻吩的 2 位），可以表现出光致变色闭环，以及光致变色和电致变色开环。

  DOI：

  10.1246/cl.2004.1006
• 作为产物：
  描述：

  4-溴-5-甲基噻吩-2-硼酸 在 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 1,2-bis[2-methyl-5-(p-(N,N-dimethylamino)phenyl)-3-thienyl]perfluorocyclopentene
  参考文献：
  名称：

  Syntheses and optoelectronic properties of four photochromic dithienylethenes

  摘要：

  Four photochromic dithienylethene compounds, 1,2-bis(2-methyl-5-naphthalene-3-thienyl)perfluorocyclopentene 1a, 1,2-bis[2-methyl-5(p-fluorophenyl)-3-thienyl]perfluorocyclopentene 2a, 1,2-bis[2-methyl-5(p-ethoxyphenyl)-3-thienyl]perfluorocyclopentene 3a, and 1,2-bis[2-methyl-5(p-N,N-dimethylaminophenyl)-3-thienyl]perfluorocyclopentene 4a were synthesized, and their optoelectronic properties, such as photochromism in solution as well as in poly-methylmethacrylate (PMMA) amorphous films, fluorescences and electrochemical properties were investigated in detail. These dithienylethenes have shown good photochromic behavior both in solution and in PMMA amorphous film. All of them exhibited relatively strong fluorescence and gave a bathochromic shift upon increasing concentration in THF. The irreversible anodic oxidation of la, 2a and 4a was observed by performing cyclic voltammetry experiments. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.044

文献信息

• Highly efficient cycloreversion of photochromic dithienylethene compounds using visible light-driven photoredox catalysis
  作者：Sumin Lee、Youngmin You、Kei Ohkubo、Shunichi Fukuzumi、Wonwoo Nam

  DOI：10.1039/c3sc52900b

  日期：——

  Photochromic cis-1,2-dithienylethene (DTE) compounds are the most suitable to the application in reversible molecular memories and switches, but imbalance in the quantum yields for the chromic interconversion limits the full potentials. We have demonstrated and investigated photoelectrocatalytic cycloreversion of DTE compounds. A series of cyclometalated Ir(III) complexes served as photoredox catalysts

  光致变色顺式-1,2-二噻吩基乙烯（DTE）化合物最适合用于可逆分子存储器和开关，但用于铬互变的量子产率不平衡限制了其全部潜力。我们已经证明并研究了DTE化合物的光电催化环还原。一系列环金属化的Ir（III配合物用作光氧化还原催化剂，以使环还原量子产率提高一个数量级。已深入研究了涉及DTE的光诱导氧化，电催化开环和还原终止的机理。纳秒瞬态光谱技术用于直接监测DTE和光氧化还原催化剂之间的双向电子转移。发现氧化光诱导的电子转移受扩散控制并且位于马库斯法线区域，而竞争性反向电子转移发生在马库斯反转区域。这一新发现建立了对反向电子转移而不是光诱导电子转移的合成控制，可以改善光电催化的性能。综合研究 包括使用变温停止流UV-vis吸收光谱进行动力学研究以及基于基于时间的密度泛函理论的量子化学计算，还可以鉴定经历热，电催化环还原的自由基中间体。最后，基于马库斯电子转移理论的分析表明，在终止步骤中激发
• High response photochromic films based on D–A diarylethenes and their application in holography
  作者：Maria Chiara Mantero、Luca Oggioni、Giorgio Pariani、Fausto Ortica、Silvano Tosi、Maurizio Canepa、Chiara Bertarelli、Matteo Tommasini、Andrea Bianco

  DOI：10.1039/d0ra05535b

  日期：——

  Photochromic diarylethenes with D–A structure are good candidates in holography thanks to their very large modulation of the complex refractive index.

  具有D-A结构的光致变色二芳乙烯化合物是全息技术中的理想候选者，因为它们具有非常大的复折射率调制能力。
• Syntheses and optoelectronic properties of four photochromic dithienylethenes
  作者：Shouzhi Pu、Tianshe Yang、Jingkun Xu、Liang Shen、Guizhen Li、Qiang Xiao、Bing Chen

  DOI：10.1016/j.tet.2005.04.044

  日期：2005.7

  Four photochromic dithienylethene compounds, 1,2-bis(2-methyl-5-naphthalene-3-thienyl)perfluorocyclopentene 1a, 1,2-bis[2-methyl-5(p-fluorophenyl)-3-thienyl]perfluorocyclopentene 2a, 1,2-bis[2-methyl-5(p-ethoxyphenyl)-3-thienyl]perfluorocyclopentene 3a, and 1,2-bis[2-methyl-5(p-N,N-dimethylaminophenyl)-3-thienyl]perfluorocyclopentene 4a were synthesized, and their optoelectronic properties, such as photochromism in solution as well as in poly-methylmethacrylate (PMMA) amorphous films, fluorescences and electrochemical properties were investigated in detail. These dithienylethenes have shown good photochromic behavior both in solution and in PMMA amorphous film. All of them exhibited relatively strong fluorescence and gave a bathochromic shift upon increasing concentration in THF. The irreversible anodic oxidation of la, 2a and 4a was observed by performing cyclic voltammetry experiments. (c) 2005 Elsevier Ltd. All rights reserved.
• Photoelectrochromic Dithienylperfluorocyclopentene Derivatives
  作者：Xin-Hong Zhou、Fu-Shi Zhang、Peng Yuan、Fan Sun、Shou-Zhi Pu、Fu-Qun Zhao、Chen-Ho Tung

  DOI：10.1246/cl.2004.1006

  日期：2004.8

  Dithienylperfluorocyclopentene derivatives that bear alkyl substituents connected onto the two carbon atoms of the thiophene heterocycles where, in their ring-closed form, the new C–C single bond is formed (the 2-positions of the thiophene), can exhibit photochromic ring-closing, and both photochromic and electrochromic ring-opening.

  二噻吩基全氟环戊烯衍生物，带有连接到噻吩杂环的两个碳原子上的烷基取代基，在其闭环形式中，形成新的 C-C 单键（噻吩的 2 位），可以表现出光致变色闭环，以及光致变色和电致变色开环。