1,2-bis(3-methyl-2-thienyl)-perfluorocyclopentene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 1,2-bis(3-methyl-2-thienyl)-perfluorocyclopentene
• 英文别名: 1,2-bis(3-methyl-2-thienyl)perfluorocyclopentene；2-[3,3,4,4,5,5-hexafluoro-2-(3-methylthiophen-2-yl)cyclopenten-1-yl]-3-methylthiophene
• 化学式: C₁₅H₁₀F₆S₂
• 分子量: 368.367
• InChiKey: FOBHDKNFKUIPRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  1,2-bis(3-methyl-2-thienyl)-perfluorocyclopentene 在 正丁基锂 、 甲酸:三乙胺 1:1 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 1,2-bis(5-(2-carboxyethyl)-3-methyl-2-thienyl)hexafluorocyclopentene
  参考文献：
  名称：

  Phototriggered formation and disappearance of surface-confined self-assembly composed of photochromic 2-thienyl-type diarylethene: a cooperative model at the liquid/solid interface

  摘要：

  通过STM研究了2-D表面上的光响应自组装，并通过合作模型对行为进行了分析。

  DOI：

  10.1039/c3cc48895k
• 作为产物：
  描述：

  7,7,8,8,9,9-Hexafluoro-3a,3b-dimethyl-3b,7,8,9-tetrahydro-3aH-1,6-dithia-trindene 以 正己烷 为溶剂， 生成 1,2-bis(3-methyl-2-thienyl)-perfluorocyclopentene
  参考文献：
  名称：

  1,2-双（2-噻吩基）全氟环戊烯衍生物的光致变色：取代对活性碳原子的影响

  摘要：

  在这项工作中，我们制备了一种新的1,2-双（3-氰基噻吩-2-基）全氟环戊烯，在两个活性碳原子上均具有吸电子氰基。此外，我们通过比较具有R =的衍生物的吸收波长和量子产率，研究了活性碳原子对1,2-双（3-R-取代的噻吩-2-基）全氟环戊烯衍生物的光致变色性质的取代作用。氰基，甲基和甲氧基。随着取代基的给电子特性的增加，由UV辐射产生的闭环异构体的吸收带移至更长的波长。在两个活性碳原子上均具有氰基的闭环异构体在427 nm处具有吸收带（λmax），而甲基和甲氧基衍生物的那些分别在432和481 nm处具有能带。具有氰基的衍生物显示最大的环还原量子产率（0.45），并且该产率随着取代基的给体特性的增加而降低。理论计算表明，具有氰基的闭环异构体的激发态具有最高能量，因为在激发电势表面上开环没有障碍。

  DOI：

  10.1021/jp3092978

文献信息

• Self-assembly of photochromic diarylethene–peptide conjugates stabilized by β-sheet formation at the liquid/graphite interface
  作者：Nobuhiko Nishitani、Takashi Hirose、Kenji Matsuda

  DOI：10.1039/c9cc02093d

  日期：——

  Two-dimensional (2-D) self-assembly of diarylethene (DAE)–peptide conjugates at the octanoic acid/graphite interface was investigated by scanning tunnelling microscopy (STM). The open-ring isomer of a DAE–peptide conjugate formed a stable 2-D molecular assembly with an antiparallel β-sheet structure. Quantitative analysis of surface coverage depending on concentration revealed a stronger stabilization

  通过扫描隧道显微镜（STM）研究了二芳基乙烯（DAE）-肽共轭物在辛酸/石墨界面的二维（2-D）自组装。DAE-肽共轭物的开环异构体形成具有反平行β-折叠结构的稳定的2D分子组装体。取决于浓度的表面覆盖率的定量分析显示，寡肽的稳定作用要强于具有相似侧链长度的烷基。
• Unusual Photochromic Behavior of C3-Methoxy-Substituted Bis(2-thienyl)perfluorocyclopentene
  作者：Kingo Uchida、Hibiki Sumino、Yumiko Shimobayashi、Yousuke Ushiogi、Atsushi Takata、Yuko Kojima、Satoshi Yokojima、Seiya Kobatake、Shinichiro Nakamura

  DOI：10.1246/bcsj.82.1441

  日期：2009.11.15

  A bis(2-thienyl)perfluorocyclopentene having methoxy groups at both reactive carbon atoms was synthesized and the quantum yields of cyclization and cycloreversion reactions were found to be 0.29 and 0.27, respectively. Usual bis(3-thienyl)perfluorocyclopentenes with methoxy groups at both reactive carbon atoms show much lower cycloreversion quantum yields. The unusual large yield was explained by theoretical methods. Additionally the compound did not show any coloration in crystalline state upon UV irradiation, even though the distance between both reactive carbon atoms is less than 4 Å. The reason was discussed by using the crystallographic data.

  合成了一种在两个活性碳原子上都有甲氧基的双(2-噻吩基)全氟环戊烯，发现其环化和环化反应的量子产率分别为 0.29 和 0.27。通常在两个活性碳原子上都含有甲氧基的双(3-噻吩基)全氟环戊烯的环化量子产率要低得多。理论方法可以解释这种不寻常的高产率。此外，尽管两个反应碳原子之间的距离小于 4 Å，但该化合物在紫外线照射下的结晶状态并未出现任何色变。
• Direct Observation of Cation Radicals of a Diarylethene during Oxidative Ring-opening Reaction
  作者：Kenji Matsuda、Satoshi Yokojima、Yoshihisa Moriyama、Shinichiro Nakamura、Masahiro Irie

  DOI：10.1246/cl.2006.900

  日期：2006.8

  The ESR spectrum of a diarylethene was measured during electrochemical oxidative ring-opening reaction of the closed-ring isomer. The spectrum was simulated by UB3LYP/cc-pVTZ method to reveal that ...

  在闭环异构体的电化学氧化开环反应过程中测量了二芳基乙烯的 ESR 光谱。通过UB3LYP/cc-pVTZ方法模拟光谱，揭示...
• Kinetic Analysis of the Photochemical Paths in Asymmetric Diarylethene Dimer
  作者：Yae Hiroyasu、Kenji Higashiguchi、Chihiro Shirakata、Masataka Sugimoto、Kenji Matsuda

  DOI：10.1002/chem.202300126

  日期：2023.8.15

  An asymmetric diarylethene dimer composed of two different diarylethenes exhibited multicolor photochromism and generated four isomers. Photochemical paths such as quantum yields, lifetimes, and rate constants were evaluated from the points of the dimer- and unit-based models. The m-phenylene spacer regulates the rate of energy transfer to be similar value of photoisomerization.

  由两种不同二芳基乙烯组成的不对称二芳基乙烯二聚体表现出多色光致变色并产生四种异构体。从基于二聚体和基于单元的模型的角度评估了光化学路径，例如量子产率、寿命和速率常数。间亚苯基间隔基将能量转移速率调节至与光异构化相似的值。
• Method of changing color of a toy and colour changing toy
  申请人：THE PILOT INK CO., LTD.

  公开号：EP1415692A1

  公开（公告）日：2004-05-06

  A toy comprises a toy element comprising a photochromic layer which contains a photochromic compound having a photo memory function (color-memorizing photochromic property), maintains a coloring state by developing a color through the irradiation of ultraviolet rays or sunlight containing ultraviolet rays and changes into decolorizing state through its decolorization by the irradiation of visible light, and a color-changing means which contains at least one of an ultraviolet ray absorbent and a light-shading pigment capable of shading at least ultraviolet rays, changes the photochromic compound of the coloring state into decolorizing state by cutting off ultraviolet rays of sunlight and thereby effecting irradiation of visible light, and maintains the changed state, wherein a function to memorize and maintain coloring and decolorizing states alternately is expressed by arranging the color-changing means under such a condition that it is covering or not covering the photochromic layer.

  一种玩具包括一个由光致变色层和一个变色装置组成的玩具元件，光致变色层包含具有光记忆功能（颜色记忆光致变色特性）的光致变色化合物，通过紫外线或含有紫外线的阳光照射显色来保持着色状态，并通过可见光照射使其脱色而变为脱色状态，变色装置包含紫外线吸收剂和至少能遮蔽紫外线的遮光颜料中的至少一种、通过切断太阳光中的紫外线，从而实现可见光的照射，将着色状态的光致变色化合物变为脱色状态，并保持改变后的状态，其中，通过在覆盖或不覆盖光致变色层的条件下布置变色装置，可实现交替记忆和保持着色和脱色状态的功能。