1,2-bis(6-carboxy-2-methylbenzo[b]thiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopentene | 159617-27-3

• 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(6-carboxy-2-methylbenzo[b]thiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopentene
• 英文别名: 3,3'-(3,3,4,4,5,5-Hexafluorocyclopentene-1,2-diyl)bis(2-methylbenzo[b]thiophene-6-carboxylic acid)；3-[2-(6-carboxy-2-methyl-1-benzothiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-2-methyl-1-benzothiophene-6-carboxylic acid
• CAS: 159617-27-3
• 化学式: C₂₅H₁₄F₆O₄S₂
• 分子量: 556.506
• InChiKey: VIMXQQFSIBVJJA-UHFFFAOYSA-N

物化性质

• 沸点：
  683.1±55.0 °C(predicted)
• 密度：
  1.65±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,2-bis(6-carboxy-2-methylbenzo[b]thiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopentene 在 氯化亚砜 作用下， 生成
  参考文献：
  名称：

  由双芳烃和笼式硅氧烷组成的无机-有机杂化光机械晶体

  摘要：

  光机械材料由于其广泛的潜在应用而受到越来越多的关注。本文报道了由二芳基乙烯和通过酰胺键连接的多面体低聚倍半硅氧烷（POSS）组成的光响应性无机-有机杂化分子的设计。在溶液中进行紫外线照射后，二芳基乙烯的POSS改性提高了从开环异构体到闭环异构体的转化率。当引入异丁基取代的POSS时，获得具有长的针状形态的氢键合分子晶体。这些晶体在紫外线（UV）和可见光（Vis）照射下具有可逆的光致变色响应和光诱导的宏观弯曲。

  DOI：

  10.1021/acs.chemmater.9b02941
• 作为产物：
  描述：

  2-甲基苯并噻吩 在 正丁基锂 、 sodium perchlorate 、 溴 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 硝基苯 为溶剂， 反应 10.5h， 生成 1,2-bis(6-carboxy-2-methylbenzo[b]thiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopentene
  参考文献：
  名称：

  光电聚合物材料：交联液晶聚合物与同构二芳烃的光响应行为

  摘要：

  制备了具有介晶二芳基乙烯的交联液晶（LC）聚合物，以证明将交联光致变色LC聚合物用作光移动材料的通用策略。暴露于紫外线下导致二芳基乙烯生色团发生光环化后，交联的聚合物薄膜会向光化光源弯曲。通过可见光照射，使闭环变成开环异构化，弯曲的薄膜恢复到初始的平坦状态。没有可见光照射，弯曲的薄膜甚至在120°C时仍保持弯曲，这表明交联的二芳基乙烯LC聚合物具有很高的热稳定性。

  DOI：

  10.1002/chem.201406299

文献信息

• An Optically Active Diarylethene Having Cholesterol Units: A Dopant for Photoswitching of Liquid Crystal Phases
  作者：Kingo Uchida、Yuji Kawai、Yo Shimizu、Volkmar Vill、Masahiro Irie

  DOI：10.1246/cl.2000.654

  日期：2000.6

  A diarylethene1 having cholesterol units was synthesized in an attempt to use it as a dopant to control the phase of liquid crystals. By the addition of the diarylethene, 4-cyano-4′-pentylbiphenyl (K-15)(Tokyo kasei) nematic liquid crystal showed cholesteric liquid crystalline texture. Upon irradiation with UV light, the cholesteric phase was decomposed. The cholesteric phase was recovered by visible light irradiation. The reversible photoinduced-phase change was observed by alternate irradiation with UV and visible light.

  合成了具有胆固醇单元的二芳基乙烯1，试图将其用作掺杂剂来控制液晶的相。通过添加二芳基乙烯，4-氰基-4'-戊基联苯(K-15)(东京化成)向列液晶显示出胆甾型液晶结构。当用紫外光照射时，胆甾相被分解。通过可见光照射恢复胆甾相。通过紫外光和可见光的交替照射观察到可逆的光致相变。
• Optical recording material
  申请人：Yamamoto Yuji

  公开号：US20060097225A1

  公开（公告）日：2006-05-11

  A novel photochromic liquid crystal comprising a diarylethene compound having both photochromic properties and liquid crystallinity. This compound is a photochromic diarylethene compound having a mesogen group in each of the two aryl groups. The photochromic liquid crystal provides a large change in birefringence by photoisomerization or phase transition, and has high durability against repeated changes in birefringence. A side-chain polymer liquid crystal containing the above photochromic liquid crystal is useful as an optical recording material. Such an optical recording material is capable of performing light modulation by irradiation with light near Tc thereof, and is applicable to photo operator devices, optical memories, and the like. Further, the optical recording material is useful as a material for a recording layer of an optical recording medium such as an optical disk or an optical memory card.

  一种新型光致变色液晶，包括具有光致变色性和液晶性质的二芳基乙烯化合物。该化合物是一种光致变色的二芳基乙烯化合物，每个芳基中均具有一种介质基团。光致变色液晶通过光异构化或相变提供了大的双折射变化，并且对于双折射的反复变化具有高耐久性。含有上述光致变色液晶的侧链聚合物液晶可用作光记录材料。这样的光记录材料能够通过接近其Tc的光辐射进行光调制，并适用于光操作器件、光记忆等。此外，该光记录材料可用作光盘或光存储卡等光记录介质的记录层材料。
• Potochromic liquid crystals
  申请人：Frigoli Michel

  公开号：US20050258396A1

  公开（公告）日：2005-11-24

  The invention relates to novel photochromic liquid crystal materials which may be used in various electro-optic devices including liquid crystal devices. The materials can be converted into another form on irradiation by light which may make it feasible for them to be addressed by light in electro-optic devices. The materials are based on 5-membered heterocycles.

  本发明涉及一种新型光致变色液晶材料，可用于各种电光器件，包括液晶器件。这些材料可以在受到光照射后转化为另一种形式，这使得它们可以被光地址化在电光器件中使用。这些材料基于5元杂环。
• OPTICAL RECORDING MATERIAL
  申请人：ASAHI GLASS COMPANY LTD.

  公开号：EP1637573A1

  公开（公告）日：2006-03-22

  A novel photochromic liquid crystal comprising a diarylethene compound having both photochromic properties and liquid crystallinity. This compound is a photochromic diarylethene compound having a mesogen group in each of the two aryl groups. The photochromic liquid crystal provides a large change in birefringence by photoisomerization or phase transition, and has high durability against repeated changes in birefringence. A side-chain polymer liquid crystal containing the above photochromic liquid crystal is useful as an optical recording material. Such an optical recording material is capable of performing light modulation by irradiation with light near Tc thereof, and is applicable to photo operator devices, optical memories, and the like. Further, the optical recording material is useful as a material for a recording layer of an optical recording medium such as an optical disk or an optical memory card.

  一种新型光致变色液晶，由一种同时具有光致变色特性和液晶性质的二元乙烯化合物组成。这种化合物是一种光致变色二芳基烯化合物，在两个芳基中各有一个中间基团。 这种光致变色液晶可通过光异构化或相变使双折射发生较大变化，并对双折射的反复变化具有较高的耐久性。 含有上述光致变色液晶的侧链聚合物液晶可用作光学记录材料。这种光学记录材料能够通过照射其 Tc 附近的光来进行光调制，适用于光电操作器件、光学存储器等。此外，这种光学记录材料还可用作光盘或光学存储卡等光学记录介质的记录层材料。
• Photochromic Diarylethenes with Intralocking Arms
  作者：Masahiro Irie、Osamu Miyatake、Kingo Uchida、Takeshi Eriguchi

  DOI：10.1021/ja00101a010

  日期：1994.11

  1,2-Bis(2-methylbenzo[b]thiophen-3-yl)perfluorocyclopentenes with carboxyalkyl or alkyl mercaptan groups at 6 and 6' positions of the benzothiophene rings were synthesized with the aim of controlling the photochromic reactivity by external stimulation, such as chemicals or heat treatment. 1,2-Diarylethenes with heterocyclic five-membered rings have two atropisomers, and the photochromic reactivity depends on the conformation. When the molecule was fixed in a parallel conformation with intramolecular hydrogen bonds or an intramolecular disulfide linkage, the photochromic reactivity was completely inhibited. The molecule again became photoactive when the intramolecular lock was unclasped by the addition of hydrogen bond breaking or reducing agents. The diarylethene with carboxyethyl groups showed a thermal reaction threshold in decalin. At temperatures below 50 degrees C the molecule was photochemically inactive, while the photochromic property was recovered upon heating above 100 degrees C, at which temperatures the intramolecular hydrogen bonds are broken.