1,2-Diethyl-12,12,13,13,14,14-hexafluoro-6,20-bis(5-methylthiophen-2-yl)-3lambda6,23lambda6-dithiahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-4(9),5,7,10,15,17(22),18,20-octaene 3,3,23,23-tetraoxide | 1320345-87-6

• 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-Diethyl-12,12,13,13,14,14-hexafluoro-6,20-bis(5-methylthiophen-2-yl)-3lambda6,23lambda6-dithiahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-4(9),5,7,10,15,17(22),18,20-octaene 3,3,23,23-tetraoxide
• 英文别名: 1,2-diethyl-12,12,13,13,14,14-hexafluoro-6,20-bis(5-methylthiophen-2-yl)-3λ6,23λ6-dithiahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-4(9),5,7,10,15,17(22),18,20-octaene 3,3,23,23-tetraoxide
• CAS: 1320345-87-6
• 化学式: C₃₅H₂₆F₆O₄S₄
• 分子量: 752.843
• InChiKey: HFVYYHGZYPFSDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  49
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,2-Diethyl-12,12,13,13,14,14-hexafluoro-6,20-bis(5-methylthiophen-2-yl)-3lambda6,23lambda6-dithiahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-4(9),5,7,10,15,17(22),18,20-octaene 3,3,23,23-tetraoxide 以 1,4-二氧六环 为溶剂， 生成 1,2-bis(2-ethyl-6-(5-methylthiophen-2-yl)-1-benzothiophen-1,1-dioxide-3-yl)perfluorocyclopentene
  参考文献：
  名称：

  One-colour control of activation, excitation and deactivation of a fluorescent diarylethene derivative in super-resolution microscopy

  摘要：

  我们使用532纳米连续波激光在弱输出功率下，实现了对荧光二芳乙烯衍生物的激活、激发和去激活的单色控制。

  DOI：

  10.1039/c6cc10073b
• 作为产物：
  描述：

  1,2-bis(2-ethyl-6-(5-methylthiophen-2-yl)-1-benzothiophen-1,1-dioxide-3-yl)perfluorocyclopentene 以 1,4-二氧六环 为溶剂， 生成 1,2-Diethyl-12,12,13,13,14,14-hexafluoro-6,20-bis(5-methylthiophen-2-yl)-3lambda6,23lambda6-dithiahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-4(9),5,7,10,15,17(22),18,20-octaene 3,3,23,23-tetraoxide
  参考文献：
  名称：

  One-colour control of activation, excitation and deactivation of a fluorescent diarylethene derivative in super-resolution microscopy

  摘要：

  我们使用532纳米连续波激光在弱输出功率下，实现了对荧光二芳乙烯衍生物的激活、激发和去激活的单色控制。

  DOI：

  10.1039/c6cc10073b

文献信息

• Photoswitchable Turn-on Mode Fluorescent Diarylethenes: Strategies for Controlling the Switching Response
  作者：Masahiro Irie、Masakazu Morimoto

  DOI：10.1246/bcsj.20170365

  日期：2018.2.15

  has been developed. They are sulfone derivatives of 1,2-bis(2-alkyl-4-methyl-5-phenyl-3-thienyl)perfluorocyclopentenes and 1,2-bis(2-alkyl-1-benzothiophen-3-yl)perfluorocyclopentenes. By chemical modifications of the structures their switching response was tuned to meet the requirements for super-resolution fluorescence microscopies. The water-soluble derivatives have been successfully applied to acquire

  开发了一种新型的光控荧光二芳基乙烯，它没有荧光团单元，但在闭环异构体中发出强荧光（Φf ~ 0.9）。它们是 1,2-双（2-烷基-4-甲基-5-苯基-3-噻吩基）全氟环戊烯和 1,2-双（2-烷基-1-苯并噻吩-3-基）全氟环戊烯的砜衍生物。通过结构的化学修饰，它们的开关响应被调整以满足超分辨率荧光显微镜的要求。水溶性衍生物已成功应用于使用单波长可见光束获取超分辨率生物图像。
• In Situ Preparation of Highly Fluorescent Dyes upon Photoirradiation
  作者：Kakishi Uno、Hiroyuki Niikura、Masakazu Morimoto、Yukihide Ishibashi、Hiroshi Miyasaka、Masahiro Irie

  DOI：10.1021/ja204583e

  日期：2011.8.31

  Photoswitchable or photoactivatable fluorescent dyes are potentially applicable to ultrahigh density optical, memory media as well as super-resolution fluorescence imaging when the dyes are highly fluorescent and have large absorption coefficients. Here, we report on highly fluorescent photochromic dyes, which are initially nonluminous in solution under irradiation with visible light but activated to emit green or red fluorescence upon irradiation with ultraviolet (UV) light. The dyes Sa-9a are sulfone derivatives of 1,2-bis(2-ethyl-6-phenyl(or thienyl)-1-benzothiophen-3-yl)perfluorocyclopentene. It was found that substitution of phenyl or thiophene rings at 6 and 6' positions of the benzothiophene-1,1-dioxide groups is effective to increase the fluorescence quantum yields of the closed-ring isomers over 0.7 and absorption coefficients over 4 x 10(4) M-1 cm(-1). The phenyl-substituted derivatives 5a-7a undergo photocyclization reactions to produce yellow closed-ring isomers 5b-7b, which emit brilliant green fluorescence at around 550 nm (Phi(F) = 0.87-0.88) under irradiation with 488 nm light. Any absorption intensity change of the closed-ring isomers was not observed even after 100 h storage in the dark at 80 degrees C. The closed-ring isomers slowly returned to the initial open-ring isomers upon irradiation with visible (lambda > 480 nm) light. The ring-opening quantum yields (Phi(C -> O)) were measured to be (1.6-4.0) x 10(-4). When the phenyl substituents are replaced with thiophene rings, such as compounds 8a and 9a, the absorption bands of the closed-ring isomers shift to longer than 500 nm. The closed-ring isomers exhibit brilliant red fluorescences at around 620 nm (Phi(F) = 0.61-0.78) under irradiation with 532 nm light. The ring-opening reactions are very slow (Phi(C -> O) < 1 x 10(-5)). The fluorescence lifetimes of these sulfone derivatives were measured to be around 2-3 ns, which is much longer than the value of the closed-ring isomer of 1,2-bis (2-methyl-1-benzothiophen-3-yl)perfluorocyclopentene (tau(F) = 4 and 22 ps). The closed-ring isomer 8b in 1,4-dioxane exhibits excellent fatigue resistant property under irradiation with visible light (lambda > 440 nm) superior to the stability of Rhodamine 101 in ethanol
• Turn-on mode fluorescent diarylethene containing neopentyl substituents that undergoes all-visible-light switching
  作者：Ryo Nishimura、Eri Fujisawa、Ifu Ban、Ryota Iwai、Shoya Takasu、Masakazu Morimoto、Masahiro Irie

  DOI：10.1039/d2cc00554a

  日期：——

  for improving the all-visible-light switching response of turn-on mode fluorescent diarylethene derivatives. Introduction of neopentyl or isobutyl substituents at the reactive carbons (2- and 2′-positions) of an oxidized bis(benzothienyl)perfluorocyclopentene derivative, which undergoes both cyclization and cycloreversion reactions upon irradiation with visible light, was effective in increasing the cycloreversion

  本文提出了一种改进开启模式荧光二芳基乙烯衍生物的全可见光切换响应的策略。在氧化的双（苯并噻吩基）全氟环戊烯衍生物的活性碳（2-和 2'-位）上引入新戊基或异丁基取代基，在可见光照射下会发生环化和环化反应，可有效提高环化量子产率与乙基取代衍生物的产率相比，提高了一个或两个数量级。通过引入新戊基或异丁基取代基没有观察到对环化和荧光量子产率的任何显着影响。
• One-colour control of activation, excitation and deactivation of a fluorescent diarylethene derivative in super-resolution microscopy
  作者：Yuhei Arai、Syoji Ito、Hajime Fujita、Yusuke Yoneda、Takahiro Kaji、Satoshi Takei、Ryota Kashihara、Masakazu Morimoto、Masahiro Irie、Hiroshi Miyasaka

  DOI：10.1039/c6cc10073b

  日期：——

  We demonstrated one-colour control of activation, excitation and deactivation of a fluorescent diarylethene derivative by using a 532 nm CW laser at a weak output power.

  我们使用532纳米连续波激光在弱输出功率下，实现了对荧光二芳乙烯衍生物的激活、激发和去激活的单色控制。