1,2-bis(6-acetyl-2-methylbenzothiophen-3-yl)hexafluorocyclopentene | 159617-30-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-bis(6-acetyl-2-methylbenzothiophen-3-yl)hexafluorocyclopentene
• 英文别名: 1,2-bis(6-acetyl-2-methyl-1-benzothiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopent-1-ene；1,2-bis(6-acetyl-2-methylbenzo[b]thiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopentene；1,2-bis(6-acetyl-2-methylbenzo[b]thiophen-3-yl)hexafluorocyclopentene；1,2-bis(6-acetyl-2-methyl-1-benzothiophene-3-yl)perfluorocyclopentene；DABTF6；3,3'-(Hexafluorocyclopentene-1,2-diyl)bis(2-methyl-6-acetylbenzo[b]thiophene)；1-[3-[2-(6-acetyl-2-methyl-1-benzothiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-2-methyl-1-benzothiophen-6-yl]ethanone
• CAS: 159617-30-8
• 化学式: C₂₇H₁₈F₆O₂S₂
• 分子量: 552.561
• InChiKey: KPGVVTWTJACUEV-UHFFFAOYSA-N

物化性质

• 沸点：
  606.8±55.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.26
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,2-bis(6-acetyl-2-methylbenzothiophen-3-yl)hexafluorocyclopentene 在 sodium hydroxide 、 氯化亚砜 、 高氯酸 、 thallium(III) nitrate 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 反应 54.0h， 生成 1,2-bis<6-<<(diazomethyl)carbonyl>methyl>-2-methylbenzothiophen-3-yl>hexafluorocyclopentene
  参考文献：
  名称：

  Photochromic Diarylethenes with Intralocking Arms

  摘要：

  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.

  DOI：

  10.1021/ja00101a010
• 作为产物：
  描述：

  苯并噻吩 在 正丁基锂 、 溴 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 硝基苯 为溶剂， 反应 8.5h， 生成 1,2-bis(6-acetyl-2-methylbenzothiophen-3-yl)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

• Metal-directed synthesis of quadruple-stranded helical Eu(<scp>iii</scp>) molecular switch: a significant improvement in photocyclization quantum yield
  作者：Yuan Zhang、Yanyan Zhou、Ting Gao、Pengfei Yan、Hongfeng Li

  DOI：10.1039/d0cc05698g

  日期：——

  Metal-directed self-assembly enforces the conformation transformation of ligand from parallel to antiparallel, leading to a significant improvement on Φ_o–c and realizes a reversible on/off switching to Eu³⁺ ion emission.

  金属导向的自组装迫使配体的构象从平行向反平行转化，从而显著提高了Φo-c，并实现了对Eu3+离子发射的可逆开关。
• 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。
• 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。
• Photochromism of Thienyl-Containing Dihetarylethenes with Five-Membered Cyclic Bridges
  作者：V. A. Barachevsky、Yu. P. Strokach、M. M. Krayushkin

  DOI：10.1080/15421400590946352

  日期：2005.5.1

  Spectral-kinetic characteristics of a number of new photochromic dihetaryethenes with different five-membered cyclic bridges are measured and discussed. It was shown that these characteristics depend on a bridge structure as well as a nature of substituents in the thienyl fragments.
• Development of highly fluorescent photochromic material with high fatigue resistance
  作者：Yong-Chul Jeong、Sung Ik Yang、Eunkyoung Kim、Kwang-Hyun Ahn

  DOI：10.1016/j.tet.2006.04.029

  日期：2006.6

  Efficient and reversible fluorescence modulation with excellent photo-stability was achieved from a sulfone form of diacetyl diarylethene, 1,2-bis(6-acetyl-2-methyl-1-benzothiophene-1,1-dioxide-3-yl)perfluorocyclopentene (DABTFO4). The DABTFO4 emits strong fluorescence in the closed-ring isomer even in the absence of extra fluorophores. The fluorescence quantum yield, fatigue resistance, and photo-cyclization yield of DABTFO4 were significantly improved compared with the unsubstituted 1,2-bis(2-methyl-1-benzothiophene-1, 1-dioxide-3-yl)perfluorocyclopentene (BTFO4) and the sulfide analogue, 1,2-bis(6-acetyl-2-methyl-l-benzothiophene-3-yl)perfluorocyclopentene (DABTF6). (c) 2006 Elsevier Ltd. All rights reserved.