1,2-bis[2-methyl-5-(1,10-phenanthrolin-2-yl)-3-thienyl]hexafluorocyclopentene | 1338989-23-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 1,2-bis[2-methyl-5-(1,10-phenanthrolin-2-yl)-3-thienyl]hexafluorocyclopentene
• 英文别名: 2-[4-[3,3,4,4,5,5-Hexafluoro-2-[2-methyl-5-(1,10-phenanthrolin-2-yl)thiophen-3-yl]cyclopenten-1-yl]-5-methylthiophen-2-yl]-1,10-phenanthroline；2-[4-[3,3,4,4,5,5-hexafluoro-2-[2-methyl-5-(1,10-phenanthrolin-2-yl)thiophen-3-yl]cyclopenten-1-yl]-5-methylthiophen-2-yl]-1,10-phenanthroline
• CAS: 1338989-23-3
• 化学式: C₃₉H₂₂F₆N₄S₂
• 分子量: 724.753
• InChiKey: FXJPBIOBYTYEOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  51
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,2-bis[2-methyl-5-(1,10-phenanthrolin-2-yl)-3-thienyl]hexafluorocyclopentene 以 乙腈 为溶剂， 以90%的产率得到2-[8,8,9,9,10,10-Hexafluoro-1,2-dimethyl-14-(1,10-phenanthrolin-2-yl)-3,15-dithiatetracyclo[10.3.0.02,6.07,11]pentadeca-4,6,11,13-tetraen-4-yl]-1,10-phenanthroline
  参考文献：
  名称：

  Photochromic behavior of a bisthienylethene bearing Cu(I)-1,10-phenanthroline complexes

  摘要：

  A novel diarylethene having a 1,10-phenanthroline unit at each end of the molecule has been synthesized. Among the metal ions, it formed a stable complex with Cu(I) ions in acetonitrile. Rational structures of the Cu(I) complexes of the colorless and the photo-generated blue form have been given by PM3 semiempirical molecular orbital calculations to be 2:2 cyclic complexes for both isomers, with the complex of the open form belonging to the C-2 symmetry group while the complex of the closed form belongs to the D-2 symmetry group. Although the ring-closing quantum yield for free diarylethene in acetonitrile was 0.75, that for the complex was 0.026, due to the long distance of the bond-forming carbon atoms in the rigid (open form)(2)-Cu(I)(2) complex. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.04.003
• 作为产物：
  描述：

  2-[8,8,9,9,10,10-Hexafluoro-1,2-dimethyl-14-(1,10-phenanthrolin-2-yl)-3,15-dithiatetracyclo[10.3.0.02,6.07,11]pentadeca-4,6,11,13-tetraen-4-yl]-1,10-phenanthroline 以 乙腈 为溶剂， 生成 1,2-bis[2-methyl-5-(1,10-phenanthrolin-2-yl)-3-thienyl]hexafluorocyclopentene
  参考文献：
  名称：

  Photochromic behavior of a bisthienylethene bearing Cu(I)-1,10-phenanthroline complexes

  摘要：

  A novel diarylethene having a 1,10-phenanthroline unit at each end of the molecule has been synthesized. Among the metal ions, it formed a stable complex with Cu(I) ions in acetonitrile. Rational structures of the Cu(I) complexes of the colorless and the photo-generated blue form have been given by PM3 semiempirical molecular orbital calculations to be 2:2 cyclic complexes for both isomers, with the complex of the open form belonging to the C-2 symmetry group while the complex of the closed form belongs to the D-2 symmetry group. Although the ring-closing quantum yield for free diarylethene in acetonitrile was 0.75, that for the complex was 0.026, due to the long distance of the bond-forming carbon atoms in the rigid (open form)(2)-Cu(I)(2) complex. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.04.003

文献信息

• Photochromic behavior of a bisthienylethene bearing Cu(I)-1,10-phenanthroline complexes
  作者：Shun Uehara、Yuma Hiromoto、Stela Minkovska、Kazushi Suzuki、Takashi Ubukata、Yasushi Yokoyama

  DOI：10.1016/j.dyepig.2011.04.003

  日期：2012.2

  A novel diarylethene having a 1,10-phenanthroline unit at each end of the molecule has been synthesized. Among the metal ions, it formed a stable complex with Cu(I) ions in acetonitrile. Rational structures of the Cu(I) complexes of the colorless and the photo-generated blue form have been given by PM3 semiempirical molecular orbital calculations to be 2:2 cyclic complexes for both isomers, with the complex of the open form belonging to the C-2 symmetry group while the complex of the closed form belongs to the D-2 symmetry group. Although the ring-closing quantum yield for free diarylethene in acetonitrile was 0.75, that for the complex was 0.026, due to the long distance of the bond-forming carbon atoms in the rigid (open form)(2)-Cu(I)(2) complex. (C) 2011 Elsevier Ltd. All rights reserved.
• Solubility control of organic acid-base salts by photochromism
  作者：Yasushi Yokoyama、Yuma Hiromoto、Kazuya Takagi、Katsuhiro Ishii、Stéphanie Delbaere、Yuta Watanobe、Takashi Ubukata

  DOI：10.1016/j.dyepig.2014.10.015

  日期：2015.3

  The open form of a bisthienylethene with two phenanthroline groups at both ends of the molecule formed, upon the addition of oxalic acid, a sudden precipitation in solution. UV irradiation to the suspension induced dissolution of the precipitate together with the coloration of the solution. The chemical structure of the precipitate was investigated by low-coherence DLS, DOSY, SEM, powder XRD, and DFT calculations. Light of any wavelength is scattered when the bisthienylethene takes the open form structure while light with wavelengths longer than 800 nm is transparent for the closed form. We have, therefore, succeeded in constructing a photon-working aggregation-dissolution system which works as an optical shutter of the near-IR light as well as the prototype for the photon-working regulator of material concentration in solution. (C) 2014 Elsevier Ltd. All rights reserved.