5,6-(Hexafluorotrimethylene)-11a,11b-dihydro-11aalpha,11bbeta-dimethylbenzo[2,1-b:3,4-b']bis[1]benzothiophene | 140483-67-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 5,6-(Hexafluorotrimethylene)-11a,11b-dihydro-11aalpha,11bbeta-dimethylbenzo[2,1-b:3,4-b']bis[1]benzothiophene
• 英文别名: (1R,2R)-12,12,13,13,14,14-hexafluoro-1,2-dimethyl-3,23-dithiahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-4,6,8,10,15,17,19,21-octaene
• CAS: 140483-67-6
• 化学式: C₂₃H₁₄F₆S₂
• 分子量: 468.487
• InChiKey: ZTFKBGNXWVCWLA-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  31
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,6-(Hexafluorotrimethylene)-11a,11b-dihydro-11aalpha,11bbeta-dimethylbenzo[2,1-b:3,4-b']bis[1]benzothiophene 在 aluminum oxide 作用下， 生成 1,2-二[2-甲基苯并[B]噻吩-3-基]-3,3,4,4,5,5-六氟-1-环戊烯
  参考文献：
  名称：

  二芳基乙烯在多孔氧化铝上的光致变色：光致变色的抗疲劳性和氧化还原电位

  摘要：

  在多孔氧化铝上检查了三种二芳基乙烯衍生物的光致变色。在紫外光和可见光交替照射下，具有噻吩环的二芳基乙烯容易分解，而具有苯并噻吩环的衍生物则发生可逆的光致变色反应。分解从二噻吩乙烯的闭环异构体开始。基于化合物的氧化电位讨论了分解机理。

  DOI：

  10.1246/cl.2001.366
• 作为产物：
  描述：

  1,2-二[2-甲基苯并[B]噻吩-3-基]-3,3,4,4,5,5-六氟-1-环戊烯 以40%的产率得到5,6-(Hexafluorotrimethylene)-11a,11b-dihydro-11aalpha,11bbeta-dimethylbenzo[2,1-b:3,4-b']bis[1]benzothiophene
  参考文献：
  名称：

  Fatigue-resistant photochromic dithienylethenes by controlling the oxidation state

  摘要：

  通过控制 1,2-双（2-甲基-1-苯并噻吩-3-基）全氟环戊烯（BTF6）和 1,2-双（2,5-二甲基噻吩-3-基）全氟环戊烯（DMTF6）的氧化态，合成了高抗疲劳光致变色二噻吩。

  DOI：

  10.1039/b600754f

文献信息

• Photochromism of Bis(2-alkyl-1-benzofuran-3-yl)perfluorocyclopentene Derivatives
  作者：Tadatsugu Yamaguchi、Masahiro Irie

  DOI：10.1021/jo051372z

  日期：2005.12.1

  Photochromic diarylethene derivatives having benzofuran heteroaryl groups, bis(2-methyl-1-benzofuran-3-yl)perfluorocyclopentene and bis(2-butyl-1-benzofuran-3-yl)perfluorocyclopentene, were synthesized, and their photochromic performance was examined in hexane solution as well as in the single-crystalline phase. The compounds exhibited photochromic reactivity even in the single-crystalline phase.

  合成了具有苯并呋喃杂芳基，双（2-甲基-1-苯并呋喃-3-基）全氟环戊烯和双（2-丁基-1-苯并呋喃-3-基）全氟环戊烯的光致变色二芳基乙烯衍生物，并对其光致变色性能进行了测试。己烷溶液以及在单晶相中。该化合物甚至在单晶相中也显示出光致变色反应性。
• Thermally irreversible photochromic systems. Reversible photocyclization of 1,2-bis (2-methylbenzo[b]thiophen-3-yl)perfluorocyclocoalkene derivatives
  作者：Makoto Hanazawa、Ritsuo Sumiya、Yukio Horikawa、Masahiro Irie

  DOI：10.1039/c39920000206

  日期：——

  1,2-Bis(2-methylbenzo[b]thiophen-3-yl)perfluorocylopentenes undergo thermally irreversible photochromic reactions in which colouration/decolouration cycles can be repeated more than 104 times without significant loss of performance.

  1,2-双（2-甲基苯并[ b ]噻吩-3-基）全氟环戊烯经历热不可逆的光致变色反应，其中着色/脱色循环可以重复进行10 4次以上，而不会显着降低性能。
• Ring Closure Reaction Pathway of a Diarylethene in Solution Using Femtosecond Time‐resolved Fluorescence Spectra
  作者：Kiho Seo、Intae Eom、Sangdeok Shim、Chul Hoon Kim、Taiha Joo

  DOI：10.1002/bkcs.11689

  日期：2019.4

  by means of time‐resolved fluorescence spectra. Compared with a single wavelength probe, direct measurement of the emission spectra during the reaction provides unambiguous and straightforward picture for the ring closure reaction pathway. We observe two different emission bands in the fluorescence of the open ring isomer. From the global analysis for the spectra, we obtain <1 ps time constant for

  通过时间分辨荧光光谱研究了1,2-双（2-甲基苯并[ b ]噻吩-3-基）六氟环戊烯的光致变色闭环反应动力学。与单波长探针相比，反应过程中发射光谱的直接测量为闭环反应路径提供了明确而直接的图像。我们在开环异构体的荧光中观察到两个不同的发射带。从光谱的整体分析，我们得出在极性溶剂中闭环反应的时间常数小于1 ps。此外，化合物的闭环反应完全在超快的时间尺度上发生。无反应的并行构象异构体以150 ps的时间常数衰减到基态。
• Effect of Imino Nitroxyl and Nitronyl Nitroxyl Groups on the Photochromic Reactivity of Diarylethenes
  作者：Naoki Tanifuji、Kenji Matsuda、Masahiro Irie

  DOI：10.1021/ol051463i

  日期：2005.8.1

  Diarylethene derivatives having imino nitroxide and nitronyl nitroxide have been prepared to examine the effect of the radical substituents on the photochromic reactivity of 1,2-bis(2-methyl-1-benzothiophen-3-yl)perfluorocyclopentene. These radical substituents reduce the quantum yields of both cyclization and cycloreversion reactions. The nitronyl nitroxyl moiety is more effective to suppress the reactivity in comparison with the imino nitroxide moiety.
• Photochromism of diarylethenes having nitronyl nitroxides
  作者：Kenji Matsuda、Masahiro Irie

  DOI：10.1016/s0040-4039(00)00209-4

  日期：2000.4

  The photoreactivities of photochromic diarylethenes having nitronyl nitroxide radicals were studied in terms of the measurement of the quantum yields and the conversions in the photostationary state. (C) 2000 Elsevier Science Ltd. All rights reserved.