3-[2-(2,4-二甲基噻吩-3-基)-3,3,4,4,5,5-六氟环戊烯-1-基]-2,4-二甲基噻吩 | 170658-51-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 3-[2-(2,4-二甲基噻吩-3-基)-3,3,4,4,5,5-六氟环戊烯-1-基]-2,4-二甲基噻吩
• 英文名称: 1,2-bis(2,4-dimethyl-3-thienyl)perfluorocyclopentene
• 英文别名: 3,3'-(3,3,4,4,5,5-Hexafluorocyclopent-1-ene-1,2-diyl)bis(2,4-dimethylthiophene)；3-[2-(2,4-dimethylthiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-2,4-dimethylthiophene
• CAS: 170658-51-2
• 化学式: C₁₇H₁₄F₆S₂
• 分子量: 396.421
• InChiKey: COYIBBPRMYKONB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-[2-(2,4-二甲基噻吩-3-基)-3,3,4,4,5,5-六氟环戊烯-1-基]-2,4-二甲基噻吩 在 碘 、 碘酸 作用下， 以 四氯化碳 为溶剂， 反应 6.0h， 生成 1,2-bis(5''-iodo-2,4-dimethyl-5,2':5',2''-terthiophen-3-yl)perfluorocyclopentene
  参考文献：
  名称：

  Photochromism of diarylethenes having thiophene oligomers as the aryl groups

  摘要：

  Diarylperfluorocyclopentenes having thiophene oligomers as the aryl groups were synthesized and their photochromic reactivity was examined. The cylization quantum yields were scarcely affected by the oligomer chain length, while the ring-opening quantum yields dramatically decreased with the increasing number of the thiophene rings, The low quantum yield of a 1,2-bis(5 ''-cyano-2,4-dimethyl-5,2':5',2 ''-terthiophen-3-yl)perfluorocyclopentene closed-ring form was increased as large as 34 times by raising the reaction temperature from 25 degrees C to 150 degrees C. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00558-9
• 作为产物：
  描述：

  2,4-二甲基噻吩 在 正丁基锂 、 水 、 溴 作用下， 以 溶剂黄146 为溶剂， 反应 5.25h， 生成 3-[2-(2,4-二甲基噻吩-3-基)-3,3,4,4,5,5-六氟环戊烯-1-基]-2,4-二甲基噻吩
  参考文献：
  名称：

  Photochromism of Dithienylethenes with Electron-Donating Substituents

  摘要：

  Bis(2,4-dimethyl-5-phenylthiophene-3-yl) having hydrogen, methoxy, diethylamino, or cyano substituents at para-positions of the phenyl groups were synthesized to reveal the effect of the substitution on the absorption coefficient epsilon of the closed-ring forms and the photochemical reactivity. Electron-donating substituents, such as methoxy or diethylamino groups, were found to be effective to increase the absorption coefficient and to decrease the ring-opening quantum yield. The cyclization quantum yield was scarcely affected by the substitution. The conversion from the open- to the closed-ring forms of the diethylamino-substituted compound in the photostationary state under irradiation with 313 nm light was close to 100%.

  DOI：

  10.1021/jo00130a035

文献信息

• A Photochromic Dithienylethene That Turns Yellow by UV Irradiation
  作者：Kingo Uchida、Masahiro Irie

  DOI：10.1246/cl.1995.969

  日期：1995.11

  1,2-Bis(3,5-dimethyl-2-thienyl)perfluorocyclopentene which shows a reversible color change from colorless to yellow by UV irradiation was synthesized. The color of the photogenerated closed-ring forms was dependent on the substitution position of the thiophene rings to the perfluorocyclopentene moiety.

  合成了1,2-双(3,5-二甲基-2-噻吩基)全氟环戊烯，该化合物在紫外线照射下表现出从无色到黄色的可逆颜色变化。光生闭环形式的颜色依赖于噻吩环与全氟环戊烯部分的取代位置。
• Syntheses and Photochromic Properties of Diarylethenes with a Naphthalene and a Thiophene Ring
  作者：Michinori Takeshita、Erika Mizukami、Kazuto Murakami、Yuta Wada、Yuji Matsuda

  DOI：10.1002/ejoc.201301677

  日期：2014.6

  Two types of diarylethene, each of which contains a naphthalene and a thiophene ring, were synthesized, and their photochromic properties were studied. The photochromic properties are dependent on the bridge position of the thiophene ring. The cycloreversion of one of the closed forms of some of the diarylethenes occurred almost photon quantitatively, and the photochromic reactions were thermally irreversible

  合成了两种分别含有萘和噻吩环的二芳基乙烯，并研究了它们的光致变色性能。光致变色特性取决于噻吩环的桥位置。一些二芳基乙烯的一种封闭形式的环回复几乎是定量地发生在光子上，并且光致变色反应是热不可逆的，至少在室温下是这样。
• Efficient Photocyclization of Dithienylethene Dimer, Trimer, and Tetramer:  Quantum Yield and Reaction Dynamics
  作者：Teruaki Kaieda、Seiya Kobatake、Hiroshi Miyasaka、Masataka Murakami、Nobuyuki Iwai、Yasushi Nagata、Akira Itaya、Masahiro Irie

  DOI：10.1021/ja0115722

  日期：2002.3.1

  Multi-dithienylethene arrays, in which two, three, or four 1,2-bis(2,4-dimethylthiophen-3-yl)perfluorocyclopentenes are ethynylene-bridged, were synthesized. Upon irradiation with ultraviolet light the hexane solutions of the arrays turned violet-blue and the color disappeared by irradiation with visible light. The quantum yields of photocyclization reactions successively increased from 0.21 to 0.40 by increasing

  合成了多 dithienylethene 阵列，其中两个、三个或四个 1,2-双 (2,4-二甲基噻吩-3-基) 全氟环戊烯被乙炔桥接。在用紫外光照射后，阵列的己烷溶液变成紫蓝色，并且在可见光照射下颜色消失。通过将阵列中的二噻吩基乙烯部分的数量从 1 增加到 4，光环化反应的量子产率从 0.21 连续增加到 0.40。皮秒激光光解以及荧光去极化实验证实，阵列中从光化学惰性平行构象异构体到光活性反平行构象异构体的有效激发能量迁移导致高量子产率。
• PHOTOCHROMIC LATEX INK
  申请人：XEROX CORPORATION

  公开号：US20150153479A1

  公开（公告）日：2015-06-04

  A photochromic latex ink includes an organic polymer; optionally a colorant, and a photochromic compound. The photochromic ink composition has an average particle size from about 20 nm to about 600 nm. The photochromic ink composition is capable of reversibly converting from a first color to a second color in response to a predetermined wavelength scope.

  一种光致变色乳胶墨水，包括有机聚合物；可选颜料和光致变色化合物。光致变色墨水组合物的平均粒径为大约20纳米到约600纳米。光致变色墨水组合物能够在预定波长范围内可逆地从第一种颜色转变为第二种颜色。
• Excited State Energy Migration and Photochromic Reaction in 1,2-Bis(2,4-dimethyl-3-thienyl)perfluorocyclopentene Single Crystal
  作者：Seiya Kobatake、Hiroaki Muto、Masahiro Irie

  DOI：10.1246/cl.2006.102

  日期：2006.1

  An excited state energy migration was found to compete with a photocyclization reaction in the single crystal of 1,2-bis(2,4-dimethyl-3-thienyl)perfluorocyclopentene.

  在 1,2-双(2,4-二甲基-3-噻吩基)全氟环戊烯的单晶体中，发现激发态能量迁移与光环化反应发生了竞争。