5-[4-(Azidomethyl)phenyl]-3-[2-[5-[4-(azidomethyl)phenyl]-2-methylthiophen-3-yl]-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-2-methylthiophene | 1536084-81-7

• 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: 5-[4-(Azidomethyl)phenyl]-3-[2-[5-[4-(azidomethyl)phenyl]-2-methylthiophen-3-yl]-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-2-methylthiophene
• 英文别名: 5-[4-(azidomethyl)phenyl]-3-[2-[5-[4-(azidomethyl)phenyl]-2-methylthiophen-3-yl]-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-2-methylthiophene
• CAS: 1536084-81-7
• 化学式: C₂₉H₂₀F₆N₆S₂
• 分子量: 630.64
• InChiKey: HBXHOMPPTPHLPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  43
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  85.2
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5-[4-(Azidomethyl)phenyl]-3-[2-[5-[4-(azidomethyl)phenyl]-2-methylthiophen-3-yl]-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-2-methylthiophene 、 2-炔丙基-四-O-乙酰基-β-D-吡喃葡萄糖苷 在 copper(II) sulfate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以62%的产率得到[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[1-[[4-[4-[3,3,4,4,5,5-hexafluoro-2-[2-methyl-5-[4-[[4-[[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxymethyl]triazol-1-yl]methyl]phenyl]thiophen-3-yl]cyclopenten-1-yl]-5-methylthiophen-2-yl]phenyl]methyl]triazol-4-yl]methoxy]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  The effects of phenyl-bridged glucosyltriazolyl groups on the properties of water-soluble diarylethene derivatives

  摘要：

  Three water-soluble diarylethenes with glycosyltriazolyl groups and variable phenyl units have been synthesized, and their properties, such as water solubility, photochromism, and fluorescence have been discussed. Upon alternating irradiation with UV and visible light, each of the diarylethenes exhibited favorable photochromism and functioned as fluorescent switches in water. Experimental results showed that their water solubility as well as absorption features, cyclization quantum yields, photoconversion ratios, thermal stability, and fatigue resistance exhibited a strong correlation with the number of phenyl-bridged glucosyltriazolyl groups in diarylethene systems. The absorption maximum, thermal stability, and fatigue resistance were significantly improved, but the water solubility and fluorescent modulation efficiency were suppressed with the increase of the number of phenyl-bridged glucosyltriazolyl groups for these diarylethene derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.037

文献信息

• A novel full symmetric diarylethene‐based ratiometric fluorescent sensor for lysine and the application for a logic circuit
  作者：Zifan Zhu、Yuesong Wang、Haichang Ding、Congbin Fan、Yayi Tu、Gang Liu、Shouzhi Pu

  DOI：10.1002/bio.3988

  日期：2021.5

  A novel diarylethene-based ratiometric fluorescent sensor with full symmetric structure, 1o, was designed and synthesized successfully. 1o could identify lysine (Lys) with high selectivity and sensitivity and the fluorescence emission peak was red shifted 85 nm upon addition of Lys, which could realize ratio recognition. It exhibited excellent anti-interference performance in the presence of various amino acids in CH3CN/H2O (7/3, v/v) solution. Moreover, the limit of detection of 1o to Lys could reach 0.019 μM based on a good linear range of 0–40 μM. In addition, the fluorescence emission intensity of 1o could be turned off/on by ultraviolet/visible light due to the special structure of diarylethene. A logic circuit was designed with three inputs. The ratiometric fluorescent sensor 1o could be as a new tool and provide a new method for detection of Lys.

  成功设计并合成了一种具有全对称结构的新型二元噻吩基比率荧光传感器 1o。1o 可以高选择性、高灵敏度地识别赖氨酸（Lys），加入赖氨酸后，荧光发射峰红移 85 nm，实现了配比识别。在 CH3CN/H2O（7/3，v/v）溶液中存在多种氨基酸的情况下，它表现出优异的抗干扰性能。此外，基于 0-40 μM 的良好线性范围，1o 对 Lys 的检测限可达到 0.019 μM。此外，由于二元乙烯的特殊结构，1o 的荧光发射强度可通过紫外线/可见光关闭/打开。我们设计了一个具有三个输入端的逻辑电路。比率荧光传感器 1o 可以作为一种新工具，为检测赖氨酸提供一种新方法。