1,2-bis(5-chloro-2-methylthiophen-3-yl)ethane-1,2-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-bis(5-chloro-2-methylthiophen-3-yl)ethane-1,2-dione
• 英文别名: 1,2-Bis(5-chloro-2-methylthiophen-3yl)ethane-1,2-dione
• 化学式: C₁₂H₈Cl₂O₂S₂
• 分子量: 319.232
• InChiKey: SMYOGWLRWNWAGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-bis(5-chloro-2-methylthiophen-3-yl)ethane-1,2-dione 在 ammonium acetate 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 4,5-Bis(5-chloro-2-methylthiophen-3-yl)-2-(2-methoxyphenyl)-1-methylimidazole
  参考文献：
  名称：

  Imidazole-Based Dithienylethenes: Synthesis, Photochromism, and Effects of Metal Ions

  摘要：

  A series of imidazole-bridging dithienylethenes was synthesized by the condensation of thiophene-based diketone and methoxyl-substituted benzaldehyde. Their UVVis absorption and fluorescent spectra were investigated before and after irradiation with UV light. It is worth mentioning that the metal ions such as Cd2+, Cu2+, Fe3+ can obviously enhance the intensity of emission spectra.

  DOI：

  10.1080/15421406.2012.762497
• 作为产物：
  描述：

  2-甲基噻吩 在 N-氯代丁二酰亚胺 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 1,2-bis(5-chloro-2-methylthiophen-3-yl)ethane-1,2-dione
  参考文献：
  名称：

  Selective photoconversion of photochromic diarylethenes and their properties

  摘要：

  选择性光转化的光致变色日苯基乙烯衍生物已通过日苯基乙烯衍生物1a作为模型化合物进行了描述。经254 nm光照射，1a在无氧条件下发生光环化，生成环闭异构体1b；在有氧（空气）条件下则转变为硫内酯衍生物1c。研究发现，1b可以通过可见光照射逆转回1a，且在无氧条件下可以进行开环和闭环的光开关操作。然而，1c是光惰性，无法通过紫外光或可见光照射逆转回1a。此外，发现1c具有荧光，而1a和1b均不显示荧光。

  DOI：

  10.1039/c2nj40377c

文献信息

• Chemical control of photochromism and a multiresponsive molecular switch based on a diarylethene derivative containing naphthol
  作者：Wenju Liu、Ziyong Li、Fang Hu、Jun Yin、Guang-Ao Yu、Sheng Hua Liu

  DOI：10.1039/c4pp00093e

  日期：2014.12

  reaction of DIN was observed when it was stimulated by the addition of acid or methylation. Fluorescence quenching and the bathochromic effect occurred when DIN was stimulated by the addition of copper ions and a base, respectively. Its optical properties could be regulated by various chemical stimuli. Thus, it can potentially be utilized as a multiresponsive molecular switch.

  合成了具有通过咪唑单元（DIN）桥接的萘酚基团的光化学惰性二芳基乙烯衍生物，以表征多功能开关。在受到辐射（紫外线和可见光）刺激后，目标二芳基乙烯衍生物DIN不是光化学惰性的而是光活性的，可以将其光转化为酮化合物。此外，当通过添加酸或甲基化来刺激DIN时，观察到DIN的光致变色反应。当分别通过添加铜离子和碱来刺激DIN时，发生了荧光猝灭和红移效应。它的光学性质可以通过各种化学刺激来调节。因此，它可以潜在地用作多响应分子开关。
• A Bifunctional Metal Probe with Independent Signal Outputs and Regulable Detection Limits
  作者：Huan-huan Liu、Yi Chen

  DOI：10.1002/ejoc.200900582

  日期：2009.10

  A bifunctional metal detection system with independent signal outputs and regulable detection limits was developed by using a photochromic diarylethene with an imidazole unit as the ligand. The sensor can be used for the detection of Cu2+ by fluorescence recognition and for the detection of Na+ or K+ by colorimetric recognition. Moreover, the amount of component of the probe can be modulated and manipulated

  通过使用具有咪唑单元的光致变色二芳基乙烯作为配体，开发了具有独立信号输出和可调节检测限的双功能金属检测系统。该传感器可用于通过荧光识别检测Cu2+和通过比色识别检测Na+或K+。此外，探针的成分量可以通过光调制进行调制和操纵，从而导致可检测上限的变化；这扩大了金属离子可检测限的窗口。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• A novel strategy for estimation of selective photochromism by the fluorescence change in a multiswitchable dithienylethene system
  作者：Ziyong Li、Yanfu Xie、Chaojun He、Chaoyang Li、Yanbo Li、Huiyuan Ya

  DOI：10.1016/j.molstruc.2017.02.085

  日期：2017.6

  365 nm and 302 nm light. However, dithienylethenes 2 , 3 and 4 only underwent a photocyclization reaction in the middle switchable unit under the same conditions. Moreover, for dithienylethenes 2 and 4 , introduction of fluorine atoms on the cyclopentene evidently enhanced the photochromic properties compared with perhydro-substituted dithienylethenes 1 and 3 . And dithienylethene 3 could act as one

  摘要 Dithienylethenes 1 和 2 由三个通过咪唑桥连接的光致变色单元及其 N-甲基化衍生物 3 和 4 组成。它们的光致变色特性和荧光行为也在溶液中通过不同波长的紫外光照射进行了研究。发现二噻吩基乙烯 1 表现出选择性光致变色，这由用 365 nm 和 302 nm 光照射时的荧光变化表示。然而，二噻吩乙烯2、3和4在相同条件下仅在中间可切换单元中进行光环化反应。此外，对于二噻吩乙烯 2 和 4，与全氢取代的二噻吩乙烯 1 和 3 相比，在环戊烯上引入氟原子明显增强了光致变色性能。
• New bis‐photochromic compounds based on diarylimidazoles: Synthesis and multistimuli‐responsive optical properties
  作者：Guangliang Song、Yuwei Song、Senqiang Zhu、Jinfeng Ji、Rui Liu、Hongjun Zhu

  DOI：10.1002/bio.3989

  日期：2021.5

  Three new bis‐photochromic molecules containing two 4,5‐diarylimidazole units were synthesized and characterized. We investigated their photophysical properties and pH response characteristics in acetonitrile solutions and polymethylmethacrylate (PMMA) membranes. All compounds displayed significant pH responses for the imidazole ring in the molecular structure, which could be potentially used as pH

  合成并表征了包含两个4,5-二芳基咪唑单元的三个新的双光致变色分子。我们研究了它们在乙腈溶液和聚甲基丙烯酸甲酯（PMMA）膜中的光物理性质和pH响应特性。所有化合物在分子结构中对咪唑环均显示出显着的pH响应，可潜在用作pH探针。在紫外光下，这些化合物在溶液或PMMA膜中均表现出光致变色和“关闭”荧光特性。这种现象的机制可能是由于光异构化，即4,5-二芳基咪唑单元的开环形式转化为闭环形式。而且，诸如逻辑门之类的系统
• Synthesis of diarylethene derivatives containing various heterocycles and tuning of light-emitting properties in a turn-on fluorescent diarylethene system
  作者：Ziyong Li、Jianlong Xia、Jinhua Liang、Jingjing Yuan、Guojun Jin、Jun Yin、Guang-Ao Yu、Sheng Hua Liu

  DOI：10.1016/j.dyepig.2011.01.008

  日期：2011.9

  imidazole ring greatly affect the optical properties. The light-emitting properties can be easily tuned from blue light-emitting to yellow light-emitting fluorescence by varying the nature of the heterocycle or by simple modification of structures, which provides a new strategy for the design of novel fluorescent switches. Moreover, Cu2+, Hg2+, and Fe3+ greatly affect the fluorescence properties of diarylethene

  合成了一系列新的引入不同杂环的二芳烃及其N-甲基化衍生物，并通过NMR，MS和元素分析对产物进行了表征。每种化合物在紫外线照射下均表现出光致变色和“开启”荧光特性。已经发现，连接到咪唑环的杂环的性质和咪唑环的甲基化都极大地影响光学性质。通过改变杂环的性质或通过简单的结构修饰，可以容易地将发光性质从发蓝光的荧光调整为发黄光的荧光，这为新颖的荧光开关的设计提供了新的策略。此外，Cu 2 +，Hg2+和Fe 3+在光平稳状态下极大地影响了二芳基乙烯4的荧光性质，因此这些系统可能会部署在新型分子传感器中，以通过荧光识别来检测此类阳离子。