1,2-bis(5-carboxyl-2-methyl-3-thienyl)perfluorocyclopentene | 384330-49-8

• 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(5-carboxyl-2-methyl-3-thienyl)perfluorocyclopentene
• 英文别名: 4,4'-(perfluorocyclopent-1- ene-1,2-diyl)bis(5-methylthiophene-2-carboxylic acid)；1,2-Bis(5-carboxy-2-methyl-3-thienyl)-3,3,4,4,5,5-hexafluorocyclopentene；4-[2-(5-carboxy-2-methylthiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-5-methylthiophene-2-carboxylic acid
• CAS: 384330-49-8
• 化学式: C₁₇H₁₀F₆O₄S₂
• 分子量: 456.386
• InChiKey: IMOLFLXWIUQUFC-UHFFFAOYSA-N

物化性质

• 沸点：
  543.3±50.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,2-bis(5-carboxyl-2-methyl-3-thienyl)perfluorocyclopentene 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 16.0h， 生成 [4-[(3aR,4S,7R,7aS)-1,3-dioxo-3a,4,7,7a-tetrahydro-4,7-epoxyisoindol-2-yl]phenyl] 4-[2-[5-[4-[(3aR,4S,7R,7aS)-1,3-dioxo-3a,4,7,7a-tetrahydro-4,7-epoxyisoindol-2-yl]phenoxy]carbonyl-2-methylthiophen-3-yl]-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-5-methylthiophene-2-carboxylate
  参考文献：
  名称：

  Novel Photochromic Homopolymers Based on 1,2-Bis(3-thienyl)cyclopentenes

  摘要：

  Incorporation of photochromic molecules into polymer matrices is necessary for materials applications such as optical information processing. Several novel homopolymers were prepared from 1,2-bis(3-thienyl)cyclopentene derivatives using ring-opening metathesis polymerization techniques. Analysis by UV-vis absorption spectroscopy revealed that, in solution, they retained the appealing photochromic behavior exhibited by their respective monomers. The polymers were cast as thin films and spin-coated onto quartz substrates where the solid-state photochromic properties of the polymers were similar to those in solution.

  DOI：

  10.1021/ma0211939
• 作为产物：
  描述：

  1,2-双(5'-甲酰-2'-甲基-3'-噻吩基)全氟环戊烯 在 chromium(VI) oxide 、 硫酸 、 水 作用下， 以 丙酮 为溶剂， 以97 %的产率得到1,2-bis(5-carboxyl-2-methyl-3-thienyl)perfluorocyclopentene
  参考文献：
  名称：

  光致变色 1,2-双（噻吩基）乙烯 (BTE) 的吸收和取代之间的相关性使用改进的光谱 Hammett 方程

  摘要：

  α'-取代的 BTE（开环和闭环）的 Hammett-Brown 取代基常数与应用光谱 Hammett 方程的吸收最大值的激发能量线性相关。

  DOI：

  10.1002/ejoc.202200996

文献信息

• Full Color Light Responsive Diarylethene Inks for Reusable Paper
  作者：Woomin Jeong、Mohammed Iqbal Khazi、Dong-Hoon Park、Young-Sik Jung、Jong-Man Kim

  DOI：10.1002/adfm.201600032

  日期：2016.8

  development of rewritable paper or erasable ink appears to be an ideal approach to alleviate the increasing demand for paper. In the investigation described herein, novel light‐stimulated (UV–vis), reversible color switching, photochromic diarylethene (DE) derivatives are designed, which serve as cyan, magenta, and yellow colored ink materials for full color ink‐jet printing. The structures of the DE derivatives

  “数字化”代表了一种转变社会对纸质交流的依赖的方法。但是，到目前为止，这种策略并未对全球纸张消耗产生重大影响，在过去的几十年中，全球纸张消耗一直在增长。造纸和消费的需求不断增长，对环境的负面影响加剧。因此，开发可擦写纸或可擦墨水似乎是减轻对纸张不断增长的需求的理想方法。在本文所述的研究中，设计了新颖的光激发（UV-vis），可逆颜色切换，光致变色二芳基乙烯（DE）衍生物，它们可作为青色，品红色和黄色墨水材料用于全彩色喷墨打印。DE衍生物的结构独特，因为它们包含亲水性乙二醇链，使其能够与水基喷墨打印系统兼容。这些研究的结果表明，新的DE衍生物可以基于多次使用同一纸张的“写-擦-写”概念在打印系统中使用。对于减少纸张生产和消费的负面环境影响，该方法似乎是理想的。
• Multi-addressable supramolecular gels based on linear amino acid and bisthienylcyclopentene
  作者：Guillaume Sevez、Jiaan Gan、Jianfeng Pan、Xavier Sallenave、Annie Colin、Hassan Saadoui、Ahmed Saleh、Fritz Vögtle、Jean-Luc Pozzo

  DOI：10.1002/poc.1253

  日期：2007.11

  1,2-Bisthienylperfluorocyclopentenes covalently linked to two aggregative side-arms derived from 11-aminoundecanoic acid have been designed to self-assemble leading to the formation of supramolecular gels which could be reversibly and independently revealed or suppressed upon acidity, temperature changes and also light irradiation. Copyright © 2007 John Wiley & Sons, Ltd.

  共价连接到两个衍生自11-氨基十一酸的聚合侧链上的1,2-联苯二酚全氟环戊烯经设计可自我组装，导致超分子凝胶的形成，可在酸度，温度变化和光照下可逆地独立显示或抑制。辐射。版权所有©2007 John Wiley＆Sons，Ltd.
• Photochromic Reactions of Diarylethenes in Single Crystals with Intermolecular OH⋅⋅⋅N Hydrogen-Bonding Networks
  作者：Masakazu Morimoto、Masahiro Irie

  DOI：10.1002/chem.200501148

  日期：2006.5.24

  photochromic performance of a single crystal of a diarylethene derivative possessing carboxyl groups, 1,2-bis(5-carboxyl-2-methyl-3-thienyl)perfluorocyclopentene (1 a), and cocrystals of 1 a with 4,4'-, 2,4'-, and 2,2'-bipyridines were examined. In crystal 1 a, a discrete cyclic structure was observed, in which four 1 a molecules are linked through hydrogen bonds between the carboxyl groups. In the homocrystal

  具有羧基，1,2-双（5-羧基-2-甲基-3-噻吩基）全氟环戊烯（1a）和1a与4的共晶体的二芳基乙烯衍生物的单晶的晶体结构和光致变色性能检查了4'-，2,4'-和2,2'-联吡啶。在晶体1a中，观察到离散的环状结构，其中四个1a分子通过羧基之间的氢键连接。在均晶中，1a的光反应性和光惰性的构象体以1：1的比例存在。在1 a与联吡啶的共晶体中，在1 a和吡啶基之间形成O-HN型氢键，并且所有1 a分子都固定在光反应构象中。均晶1a和共晶均表现出光致变色性能，并且观察到从蓝紫色到青色的颜色变化，
• Photocyclization of photoswitches with high enantioselectivity in human serum albumin in an artificial environment
  作者：Koichi Kawamura、Ken Osawa、Yuta Watanobe、Yuri Saeki、Naoki Maruyama、Yasushi Yokoyama

  DOI：10.1039/c6cc10197f

  日期：——

  Three photochromic bisthienylethenes exhibited 56 - >99% enantiomer excess in photochemical ring closure upon UV irradiation when incorporated in human serum albumin dissolved in 15% acetonitrile-phosphate buffer solution and incubated...

  当掺入溶于15％乙腈-磷酸盐缓冲液的人血清白蛋白中并孵育后，三种光致变色联苯乙烯在紫外线辐射下的光化学闭环中对映体过量显示56-> 99％。
• Photoresponsive rolling and bending of thin crystals of chiral diarylethenes
  作者：Kingo Uchida、Shin-ichiro Sukata、Yuji Matsuzawa、Masako Akazawa、Jaap J. D. de Jong、Nathalie Katsonis、Yuko Kojima、Shinichiro Nakamura、Jetsuda Areephong、Auke Meetsma、Ben L. Feringa

  DOI：10.1039/b715251e

  日期：——

  Dithienylhexafluorocyclopentene with (R)- or (S)-N-phenylethylamide substituents formed rod-like and 0.2–1.0 µm-thick plate-like crystals by sublimation; upon UV irradiation, the crystals bent concavely to the incident light and finally rolled crystals were obtained; the bent crystals were reconverted to flat crystals by visible light irradiation.

  二苯并呋喃六氟环戊烯与（R）或（S）-N-苯乙基酰胺取代基通过升华形成棒状和0.2-1.0微米厚的板状晶体；在紫外光照射下，晶体向入射光弯曲凹入，最终得到卷曲的晶体；弯曲的晶体通过可见光照射重新转化为扁平晶体。