1,2-bis(3,5-dimethyl-2-thienyl)perfluorocyclopentene | 173345-44-3

• 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(3,5-dimethyl-2-thienyl)perfluorocyclopentene
• 英文别名: bis(3,5-dimethyl-2-thienyl)-perfluorocyclopentene；2-[2-(3,5-dimethylthiophen-2-yl)-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-3,5-dimethylthiophene
• CAS: 173345-44-3
• 化学式: C₁₇H₁₄F₆S₂
• 分子量: 396.421
• InChiKey: CXJJFMUZIYRLGH-UHFFFAOYSA-N

物化性质

• 沸点：
  373.4±42.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 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(3,5-dimethyl-2-thienyl)perfluorocyclopentene 在 iron(III) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (6(1)S,6(2)S)-5,7-diaza-2(3),2(3),2(4),2(4),2(5),2(5)-hexafluoro-1(3),1(5),3(3),3(5)-tetramethyl-6(1,2)cyclohexana-2(1,2)cyclopentena-1,3(2,4)dithiophenacyclooctaphan-4,7-diene
  参考文献：
  名称：

  噻吩菲-1-烯与手性桥的合成及完全非对映特异性光致变色反应

  摘要：

  制备了具有手性聚醚桥的噻吩菲-1-烯，并研究了它们的非对映特异性光致变色反应。取代的二噻吩基乙烯与各种手性合成子的偶联反应提供了噻吩菲-1-烯，即桥连的二噻吩基乙烯，为单一对映体，没有光学拆分，因此表明这些反应是非对映选择性的。在紫外线照射下，每种旋光的噻吩-1-烯异构体均异构化为相应的封闭形式对映异构体，并在可见光照射下恢复为开放形式的初始对映异构体。由于噻吩-1-烯即使在高温下也不会异构化为其他非对映异构体，因此它们经历了非对映异构的光致变色反应。根据噻吩-1-烯溶液的光致变色反应，他们在588 nm的旋光度测量中观察到了很大的变化。由于每个噻吩-1-烯的两个异构体在此波长下均无吸收，因此可以使用这些手性噻吩-1-烯进行光致变色反应的无损读出。

  DOI：

  10.1002/chem.201103970
• 作为产物：
  描述：

  (3aS,3bS)-7,7,8,8,9,9-Hexafluoro-2,3a,3b,5-tetramethyl-3b,7,8,9-tetrahydro-3aH-1,6-dithia-trindene 以 正己烷 为溶剂， 生成 1,2-bis(3,5-dimethyl-2-thienyl)perfluorocyclopentene
  参考文献：
  名称：

  Unusual Photochromic Behavior of C3-Methoxy-Substituted Bis(2-thienyl)perfluorocyclopentene

  摘要：

  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。

  DOI：

  10.1246/bcsj.82.1441

文献信息

• A Photochromic Dithienylethene That Turns Yellow by UV Irradiation
  作者：Kingo Uchida、Masahiro Irie

  DOI：10.1246/cl.1995.969

  日期：1995.11

  1,2-Bis(3,5-dimethyl-2-thienyl)perfluorocyclopentene which shows a reversible color change from colorless to yellow by UV irradiation was synthesized. The color of the photogenerated closed-ring forms was dependent on the substitution position of the thiophene rings to the perfluorocyclopentene moiety.

  合成了1,2-双(3,5-二甲基-2-噻吩基)全氟环戊烯，该化合物在紫外线照射下表现出从无色到黄色的可逆颜色变化。光生闭环形式的颜色依赖于噻吩环与全氟环戊烯部分的取代位置。
• Syntheses and Photochromic Properties of Diarylethenes with a Naphthalene and a Thiophene Ring
  作者：Michinori Takeshita、Erika Mizukami、Kazuto Murakami、Yuta Wada、Yuji Matsuda

  DOI：10.1002/ejoc.201301677

  日期：2014.6

  Two types of diarylethene, each of which contains a naphthalene and a thiophene ring, were synthesized, and their photochromic properties were studied. The photochromic properties are dependent on the bridge position of the thiophene ring. The cycloreversion of one of the closed forms of some of the diarylethenes occurred almost photon quantitatively, and the photochromic reactions were thermally irreversible

  合成了两种分别含有萘和噻吩环的二芳基乙烯，并研究了它们的光致变色性能。光致变色特性取决于噻吩环的桥位置。一些二芳基乙烯的一种封闭形式的环回复几乎是定量地发生在光子上，并且光致变色反应是热不可逆的，至少在室温下是这样。
• Synthesis and Photochromic Properties of [2.2]Thiophenophan-8-ene-1,2-diol
  作者：Michinori Takeshita、Shouhei Yamaguchi

  DOI：10.1246/cl.2011.646

  日期：2011.6.5

  A photochromic [2.2]thiophenophan-8-ene-1,2-diol, which is the first ethylene-bridged dithienylethene, has been synthesized by pinacol coupling and this compound indicates fairly good photochromic properties such as high quantum yield for photocyclization and high thermal stability.

  通过频哪醇偶联法合成了一种光致变色的[2.2]噻吩-8-烯-1,2-二醇，它是第一个乙烯桥联的二噻吩，该化合物具有相当好的光致变色特性，如高光环化量子产率和高热稳定性。
• Synthesis and photochromic properties of thiophenophan-1-enes containing a polyether bridge
  作者：Michinori Takeshita、Chinatsu Tanaka、Takashi Miyazaki、Yukari Fukushima、Miki Nagai

  DOI：10.1039/b823492b

  日期：——

  [2.n]Thiophenophan-1-ene derivatives containing a polyether bridge have been synthesized by the coupling reaction of bis(iodomethyl)dithienylethene with polyethylene glycols under high dilution conditions. All prepared [2.n]thiophenophan-1-enes were photochromic, as photocyclization of the open forms took place by UV irradiation to give a yellow solution of the closed form and their ring opening reactions occurred upon visible irradiation. There were significant differences in the quantum yields for the photocyclization reactions and the photo ring-opening reactions due to the difference in their structures since their electric properties are similar. The kinetic parameters of the thermal ring opening reaction of the closed forms of thiophenophan-1-enes were estimated and they were also dependent on their bridges.

  在高稀释条件下，通过双（碘甲基）二噻吩与聚乙二醇的偶联反应，合成了含有聚醚桥的[2.n]噻吩-1-烯衍生物。所有制备的[2.n]噻吩-1-烯都具有光色性，因为开放形式在紫外线照射下发生光环化反应，生成黄色的封闭形式溶液，而它们在可见光照射下发生开环反应。光环化反应和光开环反应的量子产率存在明显差异，这是因为它们的结构不同，而它们的电学性质相似。对封闭形式的噻吩-1-烯热开环反应的动力学参数进行了估算，这些参数也取决于它们的桥。
• Reversible Fluorescence Photoswitch based on Dye-Crosslinked Dendritic Nanoclusters for High-Contrast Imaging of Living Biological Systems
  申请人：Kim Yoonkyung

  公开号：US20120220734A1

  公开（公告）日：2012-08-30

  The present invention relates to a reversible fluorescence photoswitch based on the dye-crosslinked dendritic nanoclusters for high-contrast imaging of living biological systems. The dendritic nanocluster according to the present invention consists of two or more dendrimers crosslinked each other to have a globular shape overall, and thereby enhancing the fluorescence intensity and improving the detection sensitivity of the monomeric dendrimers. In addition, the dendritic nanocluster according to the present invention was found to internalize into a living zebrafish by both skin permeation and microinjection, independently. Further, the dendritic nanocluster according to the present invention showed low toxicity and thus it could be useful for both in vivo and in vitro imaging as well as the ex vivo cell tracking applications.

  本发明涉及一种基于染料交联树状纳米团簇的可逆荧光光开关，用于高对比度成像活体生物系统。本发明的树状纳米团簇由两个或更多树状分子交联形成，整体呈球形，从而增强了单体树状分子的荧光强度并提高了检测灵敏度。此外，本发明的树状纳米团簇被发现可以通过皮肤渗透和微注射两种方式内化到活体斑马鱼中。此外，本发明的树状纳米团簇毒性低，因此可用于体内和体外成像以及细胞追踪应用。