1,2-bis(2-methyl-6-nitro-1-benzothiophen-3-yl)perfluorocyclopentene | 247122-32-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 1,2-bis(2-methyl-6-nitro-1-benzothiophen-3-yl)perfluorocyclopentene
• 英文别名: 3-[3,3,4,4,5,5-hexafluoro-2-(2-methyl-6-nitro-1-benzothiophen-3-yl)cyclopenten-1-yl]-2-methyl-6-nitro-1-benzothiophene
• CAS: 247122-32-3
• 化学式: C₂₃H₁₂F₆N₂O₄S₂
• 分子量: 558.482
• InChiKey: UTXLLCJVJJSMHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  37
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  148
• 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-6-nitro-1-benzothiophen-3-yl)perfluorocyclopentene 生成 (1R,2R)-12,12,13,13,14,14-hexafluoro-1,2-dimethyl-6,20-dinitro-3,23-dithiahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-4(9),5,7,10,15,17(22),18,20-octaene
  参考文献：
  名称：

  A luminescent steroid-based organogel: ON–OFF photoswitching by dopant interplay and templated synthesis of fluorescent nanoparticles

  摘要：

  通过在有机胶体介质中使用二芳基乙烯光致变色化合物，实现了苝染料在开关状态之间的荧光发射调制，效率极高。荧光胶体是由掺杂苝荧光分子的类固醇低分子量有机胶体形成的。证明了光致变色化合物在该介质中的兼容性和非破坏性读取能力。掺染染料的有机胶体进一步作为模板，采用创新方法生长了物理和化学混合的荧光二氧化硅球形纳米颗粒。

  DOI：

  10.1039/c2jm34891h
• 作为产物：
  描述：

  1,2-二[2-甲基苯并[B]噻吩-3-基]-3,3,4,4,5,5-六氟-1-环戊烯 在 硝酸 、 乙酸酐 作用下， 以 溶剂黄146 为溶剂， 以58%的产率得到1,2-bis(2-methyl-6-nitro-1-benzothiophen-3-yl)perfluorocyclopentene
  参考文献：
  名称：

  单晶相中 1,2-双（2-甲基-6-硝基-1-苯并噻吩-3-基）全氟环戊烯的光致变色：闭环形式异构体的二色性

  摘要：

  发现 1,2-双 (2-甲基-6-硝基-1-苯并噻吩-3-基) 全氟环戊烯在单晶相中发生可逆的光致变色反应。在用 366 nm 光照射后，单晶在保持晶体形状的情况下变成绿色。有色晶体显示二色性。当晶体在偏振光下旋转时，颜色由黄色变为蓝色。黄色和蓝色归因于闭环形式在 465 和 600 nm 处的两个垂直电子跃迁。两个过渡矩与闭环形式异构体的短轴和长轴方向一致，它们规则地堆积在晶格中。

  DOI：

  10.1021/ja991013j

文献信息

• Photochromism of 1,2-Bis(2-methyl-6-nitro-1-benzothiophen-3-yl)perfluorocyclopentene in a Single-Crystalline Phase:  Dichroism of the Closed-Ring Form Isomer
  作者：Seiya Kobatake、Motoki Yamada、Taro Yamada、Masahiro Irie

  DOI：10.1021/ja991013j

  日期：1999.9.1

  1,2-Bis(2-methyl-6-nitro-1-benzothiophen-3-yl)perfluorocyclopentene was found to undergo a reversible photochromic reaction in the single-crystalline phase. Upon irradiation with 366-nm light, the single crystal turned green with keeping the crystal shape. The colored crystal showed dichroism. When the crystal was rotated under polarized light, the color changed from yellow to blue. The yellow and

  发现 1,2-双 (2-甲基-6-硝基-1-苯并噻吩-3-基) 全氟环戊烯在单晶相中发生可逆的光致变色反应。在用 366 nm 光照射后，单晶在保持晶体形状的情况下变成绿色。有色晶体显示二色性。当晶体在偏振光下旋转时，颜色由黄色变为蓝色。黄色和蓝色归因于闭环形式在 465 和 600 nm 处的两个垂直电子跃迁。两个过渡矩与闭环形式异构体的短轴和长轴方向一致，它们规则地堆积在晶格中。
• Control of Surface Wettability and Photomicropatterning with a Polymorphic Diarylethene Crystal upon Photoirradiation
  作者：Daichi Kitagawa、Itsuka Yamashita、Seiya Kobatake

  DOI：10.1002/chem.201100385

  日期：2011.8.22

  A photochromic diarylethene crystal of 1,2‐bis(2‐methyl‐6‐nitro‐1‐benzothiophen‐3‐yl)perfluorocyclopentene (1 a) was found to undergo a thermodynamic phase transition at 180 °C to form a needle‐like crystal, designated as 1 a‐γ. The phase transition involves melting of the initial α‐crystal and growth of the γ‐crystal. The phase transition temperature decreased with the presence of the closed‐ring

  1,2-双（2-甲基-6-硝基-1-硝基苯并噻吩-3-基）全氟环戊烯（1 a）的光致变色二芳基乙烯晶体在180°C时发生热力学相变，形成针状晶体，命名为1a-γ。相变涉及初始α晶体的熔化和γ晶体的生长。由于熔融温度降低，晶体中存在闭环异构体（1 b）时，相变温度降低。紫外线（UV）照射后，α-晶体中的化合物1a转化为1b的程度达到20％。因此，含有20％1b的α晶体甚至在170°C时也经历了相变，伴随着晶体的熔化和γ晶体的生长。通过使用光掩模在UV光照射下进行相变并随后在170℃下加热而成功地以约20μm的微晶图案的分辨率完成了通过相变进行的光微图案化。玻璃基板上的γ微晶相与水的接触角比α微晶相与水的接触角大20°。这可以归因于表面粗糙度的差异。此外，还发现加热1 a的非晶膜会形成γ微晶。在130°C下在聚（甲基丙烯酸甲酯）中溶解2分钟。结晶区域显示出比非晶区域更高的水接触角。当用UV光非
• 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。
• Color-memorizing photochromic writing instrument
  申请人：THE PILOT INK CO., LTD.

  公开号：EP1637570A1

  公开（公告）日：2006-03-22

  A color-memorizing photochromic writing instrument, which comprises a writing tip portion connected to a light-shielding tubular member or refill; and a color-memorizing photochromic ink, wherein the ink is prepared by dissolving, dispersing or suspending a diarylethene photochromic compound in a vehicle containing at least a solvent and a binder, wherein the diarylethene photochromic compound is in a coloring state, and a color-memorizing photochromic writing instrument set comprising the writing instrument and a color-changing means.

  一种颜色记忆光致变色书写工具，它包括一个与遮光管状部件或笔芯相连的书写尖端部分；一种可记色的光致变色墨水，其中墨水是通过在至少含有溶剂和粘合剂的载体中溶解、分散或悬浮二里蒽光致变色化合物制备的，其中二里蒽光致变色化合物处于着色状态；以及一套可记色的光致变色书写工具，包括书写工具和变色装置。
• Method for alternately expressing color-memorizing photochromic function in toy element, and an alternately color-memorizing photochromic toy
  申请人：THE PILOT INK CO., LTD.

  公开号：US20040135097A1

  公开（公告）日：2004-07-15

  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 contacted or non-contacted with 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，通过将变色装置布置在与光致变色层接触或不接触的条件下，可实现交替记忆和保持着色和脱色状态的功能。