2-(2,3,3,4,4,5,5-heptafluorocyclopent-1-en-1-yl)-3,5-dimethylthiophene | 173345-48-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-(2,3,3,4,4,5,5-heptafluorocyclopent-1-en-1-yl)-3,5-dimethylthiophene
• 英文别名: 2-(2,3,3,4,4,5,5-heptafluorocyclopent-1-enyl)-3,5-dimethylthiophene；(3,5-dimethyl-2-thienyl)perfluorocyclopentene
• CAS: 173345-48-7
• 化学式: C₁₁H₇F₇S
• 分子量: 304.231
• InChiKey: TTXMSRPUDBJOHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-(2,3,3,4,4,5,5-heptafluorocyclopent-1-en-1-yl)-3,5-dimethylthiophene 在 iron(III) chloride 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 2-[2-(5-tert-butyl-3-chloromethyl-2-methylphenyl)-3,3,4,4,5,5-hexafluorocyclopent-1-enyl]-4-chloromethyl-3,5- dimethylthiophene
  参考文献：
  名称：

  Syntheses and Photochromic Properties of Metacyclothiophenophan-1-enes

  摘要：

  一种由一个噻吩环、一个苯环和它们的桥组成的环状噻吩[3]-1-烯被合成出来并显示出光致变色性，而一种带有长桥的偏环噻吩-1-烯由于三个双键之间的共轭作用很小而不显示光致变色性，这是由 DFT 计算估算出来的。

  DOI：

  10.1246/cl.2009.982
• 作为产物：
  描述：

  2,4-二甲基噻吩 、 全氟环戊烯 在 正丁基锂 作用下， 生成 2-(2,3,3,4,4,5,5-heptafluorocyclopent-1-en-1-yl)-3,5-dimethylthiophene
  参考文献：
  名称：

  A Photochromic Dithienylethene That Turns Yellow by UV Irradiation

  摘要：

  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。

  DOI：

  10.1246/cl.1995.969

文献信息

• Full-Color Photochromism of a Fused Dithienylethene Trimer
  作者：Kenji Higashiguchi、Kenji Matsuda、Naoki Tanifuji、Masahiro Irie

  DOI：10.1021/ja051467i

  日期：2005.6.1

  A diarylethene fused trimer, 1-(5-(2-(3,5-dimethyl-2-thienyl)hexafluorocyclopententen-1-yl)-2,4-dimethyl-3-thienyl)-2-(5-(2-(2,4-dimethyl-5-phenyl-3-thienyl)hexafluorocyclopentene-1-yl)-2,4-dimethyl-3-thienyl)hexafluorocyclopentene, was synthesized. The diarylethene derivative showed full-color photochromic performance by choosing appropriate wavelength of light.

  二芳基乙烯稠合三聚体，1-(5-(2-(3,5-二甲基-2-噻吩基)六氟环戊烯-1-基)-2,4-二甲基-3-噻吩基)-2-(5-(2- (2,4-二甲基-5-苯基-3-噻吩基)六氟环戊烯-1-基)-2,4-二甲基-3-噻吩基)六氟环戊烯。通过选择合适的光波长，二芳基乙烯衍生物表现出全色光致变色性能。
• Structure–property relationships in normal and mixed dithienylethenes – polyoxometalates supramolecular assemblies with fast solid-state photochromic properties
  作者：Oleh Stetsiuk、Patricia Bolle、Marie Cordier、Julien Boixel、Rémi Dessapt

  DOI：10.1039/d1tc04561j

  日期：——

  isostructural series, hybrids integrating mixed DTEs exhibit faster fading processes than their normal DTE counterparts when exposed to visible light. Finally, among this new series, 2-Mo8 shows the best photochromic performances with a fast photocoloration rate associated with a high coloration contrast, a fast and complete fading process and a high cyclability.

  通过正态 ( 1 + ) 和混合 ( 2 + ) 阳离子二噻吩乙烯 (DTE) 和多金属氧酸盐 (POM) 单元的超分子组装，成功制备了五种新型高光致变色有机-无机杂化材料。单晶 X 射线衍射研究表明 (1) 3 [PM 12 O 40 ]·5ACN (M = W, Mo) ( 1-PW 12和1-PMo 12 ) 和 (2) 3 [PM 12 O 40 ]·5ACN (M = W, Mo) ( 2-PW 12和2-PMo 12 ) 是同构的，而 (2) 4 [Mo 8O 26 ]·4DMF ( 2-Mo 8 ) 是 (1) 4 [Mo 8 O 26 ]·4DMF ( 1-Mo 8 )的同种型，即最近报道的第一个 POM-DTE 离子组装体。这些材料在室温下的固态光致变色特性可以根据所使用的 DTE 和 POM 的性质进行高度调节，这已被解释为考虑了空间和电子因素。特别是，当1-PMo 12和2-PMo
• Modulating Stepwise Photochromism in Platinum(II) Complexes with Dual Dithienylethene–Acetylides by a Progressive Red Shift of Ring-Closure Absorption
  作者：Bin Li、Hui-Min Wen、Jin-Yun Wang、Lin-Xi Shi、Zhong-Ning Chen

  DOI：10.1021/ic401581q

  日期：2013.11.4

  To modulate stepwise photochromism by shifting ring-closure absorption of the dithienylethene (DTE) moiety, trans-Pt(PEt3)(2)(C C-DTE)(2) [C C-DTE = L10 (100), L20 (200), L30 (300), and L40 (400)] and cis-Pt(PEt3)(2)(L40)(2) (500) with two identical DTE-acetylides were elaborately designed. With the gradual red shift of ring-closure absorption for L1c (441 nm) -> L2c (510 nm) -> L3c (556 nm) -> L4c (602 nm), stepwise photochromism is increasingly facilitated in trans-Pt(PEt3)(2)(C C-DTE)(2) following 100 -> 200 -> 300 -> 400. The conversion percentage of singly ring-dosed 2co-4co to dually ring-closed 2cc-4cc at the photostationary state is progressively increased in the order 1cc (0%) -> 2cc (18%) -> 3cc (67%) -> 4cc (100%). Compared with trans-arranged 400, stepwise photochromism in the corresponding cis-counterpart 500 is less pronounced, ascribed to either direct conversion of 500 to 5cc or rapid conversion of 5co to 5cc. The progressively facile stepwise photocyclization following 200 -> 300 -> 400 is reasonably interpreted by gradually enhanced transition character involving LUMO+1, which is the only unoccupied frontier orbital responsible for further photocyclization of singly ring-closed 2co-4co.