1,2-bis(2-methyl-5-p-tolyl-3-thienyl)perfluorocyclopentene | 194423-31-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 1,2-bis(2-methyl-5-p-tolyl-3-thienyl)perfluorocyclopentene
• 英文别名: 3-(3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-(4-methylphenyl)(3-thienyl))cyclopent-1-enyl)-2-methyl-5-(4-methylphenyl)thiophene；1,2-bis(2-methyl-5-(4-methylphenyl)thien-3-yl)perfluorocyclopent-1-ene；3,3'-(Hexafluorocyclopentene-1,2-diyl)bis[2-methyl-5-(4-methylphenyl)thiophene]；3-[3,3,4,4,5,5-hexafluoro-2-[2-methyl-5-(4-methylphenyl)thiophen-3-yl]cyclopenten-1-yl]-2-methyl-5-(4-methylphenyl)thiophene
• CAS: 194423-31-9
• 化学式: C₂₉H₂₂F₆S₂
• 分子量: 548.616
• InChiKey: NKTWEJBJNTXUIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 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(2-methyl-5-p-tolyl-3-thienyl)perfluorocyclopentene 生成 4,4,5,5,6,6-Hexafluoro-9a,9b-dimethyl-2,8-di-p-tolyl-5,6,9a,9b-tetrahydro-4H-1,9-dithia-trindene
  参考文献：
  名称：

  单晶相中 1,2-双（2-甲基-5-苯基-3-噻吩基）全氟环戊烯的光致变色

  摘要：

  1,2-双（2-甲基-5-苯基-3-噻吩基）全氟环戊烯（1a）及其衍生物，1,2-双（2-甲基-5-对甲苯基-3-噻吩基）全氟环戊烯（2a）和 1,2-双（2-甲基-5-对叔丁基苯基-3-噻吩基）全氟环戊烯 (3a) 被发现在单晶相中发生可逆的光致变色反应。在用 366 nm 光照射后，单晶变成蓝色。通过可见光 (λ > 480 nm) 的照射，蓝色晶体变回无色。苯基对位的取代基不影响单晶相和己烷中的光环化反应速率。光环化反应的活化能几乎为零。另一方面，在单晶相的光环回复反应中观察到高达 5-10 kJ mol-1 的活化能。这些值小于在溶液中观察到的值，约。16 kJ mol-1。观察到闭环异构体 (1b) 的缓慢热环还原反应...

  DOI：

  10.1021/ja993181h
• 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 、 正己烷 为溶剂， 反应 9.33h， 生成 1,2-bis(2-methyl-5-p-tolyl-3-thienyl)perfluorocyclopentene
  参考文献：
  名称：

  单晶相中 1,2-双（2-甲基-5-苯基-3-噻吩基）全氟环戊烯的光致变色

  摘要：

  1,2-双（2-甲基-5-苯基-3-噻吩基）全氟环戊烯（1a）及其衍生物，1,2-双（2-甲基-5-对甲苯基-3-噻吩基）全氟环戊烯（2a）和 1,2-双（2-甲基-5-对叔丁基苯基-3-噻吩基）全氟环戊烯 (3a) 被发现在单晶相中发生可逆的光致变色反应。在用 366 nm 光照射后，单晶变成蓝色。通过可见光 (λ > 480 nm) 的照射，蓝色晶体变回无色。苯基对位的取代基不影响单晶相和己烷中的光环化反应速率。光环化反应的活化能几乎为零。另一方面，在单晶相的光环回复反应中观察到高达 5-10 kJ mol-1 的活化能。这些值小于在溶液中观察到的值，约。16 kJ mol-1。观察到闭环异构体 (1b) 的缓慢热环还原反应...

  DOI：

  10.1021/ja993181h

文献信息

• Regular Arrays of Rod‐Shaped Molecular Photoswitches: Synthesis, Preparation, Characterization, and Selective Photoswitching within Mono‐ and Bilayer Systems
  作者：Lukáš Severa、Carina Santos Hurtado、Igor Rončević、Milan Mašát、Guillaume Bastien、Jakub Radek Štoček、Martin Dračínský、Václav Houska、Eva Kaletová、Danielle John Garza、Ivana Císařová、Katherine Leslee A. Cimatu、Zdeněk Bastl、Jiří Kaleta

  DOI：10.1002/chem.202302828

  日期：2024.1.16

  stimuli-responsive molecules represent a unique class of smart materials with a wide range of applications. We assembled photoresponsive mono- and bilayer systems with well-defined properties from rod-shaped molecules equipped with different photoswitches. Using properly chosen chromophores, we then selectively targeted layers made of the same types of photoswitches using appropriate monochromatic light

  由刺激响应分子制成的规则二维阵列代表了一类独特的智能材料，具有广泛的应用。我们用配备不同光开关的棒状分子组装了具有明确特性的光响应单层和双层系统。使用正确选择的发色团，然后我们使用适当的单色光选择性地瞄准由相同类型的光电开关制成的层。
• 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。
• Improving the Fatigue Resistance of Diarylethene Switches
  作者：Martin Herder、Bernd M. Schmidt、Lutz Grubert、Michael Pätzel、Jutta Schwarz、Stefan Hecht

  DOI：10.1021/ja513027s

  日期：2015.2.25

  When applying photochromic switches as functional units in light-responsive materials or devices, an often disregarded yet crucial property is their resistance to fatigue during photoisomerization. In the large family of diarylethene photoswitches, formation of an annulated isomer as a byproduct of the photochromic reaction turns out to prevent the desired high reversibility for many different derivatives. To overcome this general problem, we have synthesized and thoroughly investigated the fatigue behavior of a series of diarylethenes, varying the nature of the hetaryl moieties, the bridging units, and the substituents. By analysis of photokinetic data, a quantification of the tendency for byproduct formation in terms of quantum yields could be achieved, and a strong dependency on the electronic properties of the substituents was observed. In particular, substitution with 3,5-bis(trifluoromethyl)phenyl or 3,5-bis(pentafluorosulfanyl)phenyl groups strongly suppresses the byproduct formation and opens up a general strategy to construct highly fatigue-resistant diarylethene photochromic systems with a large structural flexibility.