1-[2-methyl-5-(4-hydroxyphenyl)thien-3yl]-2-(2-methyl-5-phenylthien-3-yl)perfluorocyclopentene | 587873-58-3

• 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-methyl-5-(4-hydroxyphenyl)thien-3yl]-2-(2-methyl-5-phenylthien-3-yl)perfluorocyclopentene
• 英文别名: DTE；4-(4-(3,3,4,4,5,5-Hexafluoro-2-(2-methyl-5-phenylthiophen-3-yl)cyclopent-1-en-1-yl)-5-methylthiophen-2-yl)phenol；4-[4-[3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-phenylthiophen-3-yl)cyclopenten-1-yl]-5-methylthiophen-2-yl]phenol
• CAS: 587873-58-3
• 化学式: C₂₇H₁₈F₆OS₂
• 分子量: 536.562
• InChiKey: WMKSKINSOAWJQU-UHFFFAOYSA-N

物化性质

• 沸点：
  568.1±50.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  dihydroxy[5,10,15,20-tetrakis(p-tolyl)porphyrinato]tin(IV) 、 1-[2-methyl-5-(4-hydroxyphenyl)thien-3yl]-2-(2-methyl-5-phenylthien-3-yl)perfluorocyclopentene 以 甲苯 为溶剂， 以51%的产率得到(5,10,15,20-tetratolylporphyrinato)tin(IV)(o-OC6H4C4HS(Me)C5F6C4HS(Me)Ph)*(dichloromethane)
  参考文献：
  名称：

  轴向配位的锡（IV）卟啉二噻吩乙烯中的光调节荧光开关。

  摘要：

  已合成并充分合成了光致变色荧光团Sn（TTP）（DTE）2，其中两个1,2-二噻吩基乙烯的酚衍生物与（5,10,15,20-四甲苯基卟啉酮）锡（IV）轴向配位具有各种光谱学方法的特征。我们还研究了Sn（TTP）（DTE）2的光调节荧光转换行为。Sn（TTP）（DTE）2中的卟啉大环的荧光在很大程度上取决于1,2-二硫代丁烯光致变色开关的状态。在开放状态（Sn（TTP）（o-DTE）2）中，卟啉在410和664 nm激发时在609和664 nm处显示出高荧光强度。当通过用紫外光（约365nm）照射Sn（TTP）（o-DTE）2进行光环化反应时，卟啉大环的荧光强度降低。用波长大于500 nm的可见光进行背照射可再生Sn（TTP）（o-DTE）2，几乎恢复了原始的荧光光谱。卟啉荧光团的荧光强度通过在几个周期内在Sn（TTP）（o-DTE）2和Sn（TTP）（c-DTE）2之间进行光致变色转换而得

  DOI：

  10.1021/ic701390m
• 作为产物：
  描述：

  1-[2-methyl-5-phenyl-3-thienyl]heptafluorocyclopentene 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 6.0h， 生成 1-[2-methyl-5-(4-hydroxyphenyl)thien-3yl]-2-(2-methyl-5-phenylthien-3-yl)perfluorocyclopentene
  参考文献：
  名称：

  Solvent effect on photochromism of a dithienylperfluorocyclopentene having diethylamino group

  摘要：

  Some photochromic diarylethenes having polar substituents were synthesized, and their photochromic behavior was examined. They exhibited photochromism with the similar photoreactivity in a non-polar solvent. However, the photocyclization quantum yield of dithienylperfluorocyclopentene having diethylamino group was found to decrease in polar solvents. The yield in acetonitrile was estimated to be 60 times smaller than that in hexane. The yields determined in various solvents were found to be correlated with the solvent polarity parameter E-T(30). Such an effect was not observed in dithienylfluorocyclopentenes bearing methoxy or acetoxy group and in non-fluorinated dithienylcyclopentene bearing diethylamino group. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.053

文献信息

• Efficient “<i>turn-off</i>” fluorescence photoswitching in a highly fluorescent diarylethene single crystal
  作者：Sanae Ishida、Daichi Kitagawa、Seiya Kobatake、Sunnam Kim、Seiji Kurihara、Tuyoshi Fukaminato

  DOI：10.1039/c9cc02441g

  日期：——

  Efficient “turn-off” fluorescence photoswitching with full reversibility was successfully demonstrated in a fluorescent diarylethene single crystal.

  在荧光二芳基乙烯单晶中成功展示了高效的“关闭”荧光光开关，并具有完全可逆性。
• Giant Amplification of Photoswitching by a Few Photons in Fluorescent Photochromic Organic Nanoparticles
  作者：Jia Su、Tuyoshi Fukaminato、Jean-Pierre Placial、Tsunenobu Onodera、Ryuju Suzuki、Hidetoshi Oikawa、Arnaud Brosseau、François Brisset、Robert Pansu、Keitaro Nakatani、Rémi Métivier

  DOI：10.1002/anie.201510600

  日期：2016.3.7

  represents an extremely attractive concept. Promising fundamental and practical applications may be derived from such a photon‐saving principle. With this aim in mind, we have prepared fluorescent photochromic organic nanoparticles (NPs), showing bright red emission, complete ON–OFF contrast with full reversibility, and excellent fatigue resistance. Most interestingly, upon successive UV and visible light

  用最小的光子控制或切换来自大量分子的光信号代表了一个非常诱人的概念。这种节省光子的原理可能会带来有希望的基础和实际应用。为此，我们制备了荧光光致变色有机纳米颗粒（NPs），显示出鲜红色的发射光，具有完全可逆性的完全ON-OFF对比度，以及出色的抗疲劳性。最有趣的是，在连续的紫外线和可见光照射下，NP在非常低的光致变色转化水平（<5％）下表现出完全的荧光猝灭和恢复，导致仅一个转化的光致变色分子的荧光转化为420±20。
• Multimodal fluorescence modulation using molecular photoswitches and upconverting nanoparticles
  作者：Carl-Johan Carling、John-Christopher Boyer、Neil R. Branda

  DOI：10.1039/c2ob25368b

  日期：——

  The intensity and colour of the light emitted from upconverting nanoparticles is controlled by the state of photoresponsive dithienylethene ligands decorated onto the surface of the nanoparticles. By selectively activating one or both ligands in a mixed, 3-component system, a multimodal read-out of the emitted light is achieved.

  上转换纳米粒子发出的光的强度和颜色由装饰在纳米粒子表面的光响应二噻吩乙烯配体的状态控制。通过选择性地激活混合的三组分系统中的一个或两个配体，可以实现对发射光的多模式读取。
• Photoregulated Fluorescence Switching in Axially Coordinated Tin(IV) Porphyrinic Dithienylethene
  作者：Hee Jung Kim、Joon Hee Jang、Hyunbong Choi、Taegweon Lee、Jaejung Ko、Minjoong Yoon、Hee-Joon Kim

  DOI：10.1021/ic701390m

  日期：2008.4.1

  spectroscopic methods. We have also investigated the photoregulated fluorescence switching behavior of Sn(TTP)(DTE)2 . The fluorescence of the porphyrin macrocycle in Sn(TTP)(DTE) 2 greatly depends on the state of the 1,2-dithienyletene photochromic switch. In the open state (Sn(TTP)(o-DTE)2), the porphyrin exhibits high fluorescence intensity at 609 and 664 nm when excited at 410 nm. When the photocyclization

  已合成并充分合成了光致变色荧光团Sn（TTP）（DTE）2，其中两个1,2-二噻吩基乙烯的酚衍生物与（5,10,15,20-四甲苯基卟啉酮）锡（IV）轴向配位具有各种光谱学方法的特征。我们还研究了Sn（TTP）（DTE）2的光调节荧光转换行为。Sn（TTP）（DTE）2中的卟啉大环的荧光在很大程度上取决于1,2-二硫代丁烯光致变色开关的状态。在开放状态（Sn（TTP）（o-DTE）2）中，卟啉在410和664 nm激发时在609和664 nm处显示出高荧光强度。当通过用紫外光（约365nm）照射Sn（TTP）（o-DTE）2进行光环化反应时，卟啉大环的荧光强度降低。用波长大于500 nm的可见光进行背照射可再生Sn（TTP）（o-DTE）2，几乎恢复了原始的荧光光谱。卟啉荧光团的荧光强度通过在几个周期内在Sn（TTP）（o-DTE）2和Sn（TTP）（c-DTE）2之间进行光致变色转换而得
• Solvent effect on photochromism of a dithienylperfluorocyclopentene having diethylamino group
  作者：Seiya Kobatake、Yuko Terakawa、Hiroyuki Imagawa

  DOI：10.1016/j.tet.2009.05.053

  日期：2009.8

  Some photochromic diarylethenes having polar substituents were synthesized, and their photochromic behavior was examined. They exhibited photochromism with the similar photoreactivity in a non-polar solvent. However, the photocyclization quantum yield of dithienylperfluorocyclopentene having diethylamino group was found to decrease in polar solvents. The yield in acetonitrile was estimated to be 60 times smaller than that in hexane. The yields determined in various solvents were found to be correlated with the solvent polarity parameter E-T(30). Such an effect was not observed in dithienylfluorocyclopentenes bearing methoxy or acetoxy group and in non-fluorinated dithienylcyclopentene bearing diethylamino group. (C) 2009 Elsevier Ltd. All rights reserved.