1-[2-methyl-5-(4-formylphenyl)-3-thienyl]-2-(2-methyl-3-benzothiophenyl) perfluorocyclopentene | 1344734-18-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 1-[2-methyl-5-(4-formylphenyl)-3-thienyl]-2-(2-methyl-3-benzothiophenyl) perfluorocyclopentene
• 英文别名: 1-[(2-methyl-3-benzothienyl)]-2-[2-methyl-5-(4-formylphenyl)-3-thienyl]perfluorocyclopentene；4-[4-[3,3,4,4,5,5-Hexafluoro-2-(2-methyl-1-benzothiophen-3-yl)cyclopenten-1-yl]-5-methylthiophen-2-yl]benzaldehyde
• CAS: 1344734-18-4
• 化学式: C₂₆H₁₆F₆OS₂
• 分子量: 522.535
• InChiKey: AVKSSJAQNJUUDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  73.6
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-[2-methyl-5-(4-formylphenyl)-3-thienyl]-2-(2-methyl-3-benzothiophenyl) perfluorocyclopentene 在 4-二甲氨基吡啶 、 钾硼氢 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 生成 [4-[4-[3,3,4,4,5,5-Hexafluoro-2-(2-methyl-1-benzothiophen-3-yl)cyclopenten-1-yl]-5-methylthiophen-2-yl]phenyl]methyl 4-ethenylbenzoate
  参考文献：
  名称：

  Photochromic polymers bearing various diarylethene chromophores as the pendant: synthesis, optical properties, and multicolor photochromism

  摘要：

  合成了具有多种二芳基乙烯衍生物的光敏聚合物，这是通过对具有二芳基乙烯色团作为侧链的苯乙烯衍生物进行常规自由基聚合获得的。所有聚合物在薄膜和溶液中均表现出可逆的光致变色特性。然而，由于固态中构象结构的限制，薄膜中的光环化转化率与溶液中相比有所降低。尽管在反应初期，薄膜中的光环化和光环反转量子产率与溶液中相当，但随着反应的进行，明显的环反转量子产率下降，这源于固态中量子产率的分布。最后，合成了由三种二芳基乙烯单体组成的光敏三元聚合物，其光致变色改变为青色、品红色和黄色。这些三元聚合物通过选择性漂白过程在溶液和固态中表现出明亮的颜色，包括黑色、绿色、红色和蓝色。由二芳基乙烯衍生物组成的这种多色光敏聚合物在可重写的光致变色显示设备中具有潜在应用。

  DOI：

  10.1039/c1jm12707a
• 作为产物：
  描述：

  3,5-二溴-2-甲基噻吩 在 吡啶 、 四(三苯基膦)钯 、 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 水 、 丙酮 、 甲苯 为溶剂， 反应 41.33h， 生成 1-[2-methyl-5-(4-formylphenyl)-3-thienyl]-2-(2-methyl-3-benzothiophenyl) perfluorocyclopentene
  参考文献：
  名称：

  具有对Hg2+和Cys连续选择性的不对称全氟环 戊烯化合物及其制备方法和应用

  摘要：

  本发明公开了一种[1‑[2‑甲基‑3‑苯并噻吩基]，2‑(2‑甲基‑5‑(4‑苯基)‑(2‑甲酰基喹啉‑8‑苯并噻唑基)‑3‑噻吩基)]全氟环戊烯及其制备方法和应用。制备方法：以苯并噻吩为原料，通过碘甲烷取代、溴化，再与全氟环戊烯反应生成单取代的全氟环戊烯；以2‑甲基噻吩为原料，经溴化、通过正丁基锂与硼酸三丁酯反应，再通过Stuzki偶联反应将末端含醛基苯与噻吩环连接，再用乙二醇保护后与单取代的全氟环戊烯反应，经还原成醇羟基，再变成含亚甲基溴的，再与8‑羟基喹啉‑2‑醛基反应，最后与2‑氨基苯硫酚反应，得到目标化合物。本发明制备所得的化合物可用于连续检测特定离子和氨基酸，其选择性非常优良。

  公开号：

  CN106905312B

文献信息

• 光致变色双(N-乙基-1,8-萘酰亚胺)胺-苯并噻 吩混联型全氟环戊烯化合物及合成方法和应用
  申请人：江西科技师范大学

  公开号：CN104327060B

  公开（公告）日：2016-09-14

  本发明公开了一种光致变色双(N‑乙基‑1,8‑萘酰亚胺)胺‑苯并噻吩混联型全氟环戊烯化合物的合成方法及应用，该光致变色材料在溶液中均可保持良好的光致变色性能，并且开环态（无色态）和闭环态（呈色态）均具很好的化学和热稳定性和很好的灵敏度等优越性能，可用于荧光检测及荧光光控开关、高密度全息光存储，双重控制荧光分子开关、pH化学传感器、金属离子化学传感器等，应用前景广大。
• A new multi-addressable molecular switch based on a photochromic diarylethene with a thieno-imidazole unit
  作者：Yaming Xue、Renjie Wang、Chunhong Zheng、Gang Liu、Shouzhi Pu

  DOI：10.1016/j.tetlet.2016.03.053

  日期：2016.4

  evident color change from purple to blue. When induced by acid, the emission intensity of its open-ring isomer was enhanced by 109 fold with a notable fluorescence color change from dark to bright cyan. Moreover, its fluorescence intensity was dramatically increased when triggered by Al3+ and its emission peak was red-shifted from 460 nm to 476 nm due to the formation of a 1:2 metal/ligand complex. In

  使用二噻吩并苯并咪唑为官能团，全氟二芳基乙烯为光子控制单元，通过苯键合成了一种新型的光致变色二芳基乙烯。当被乙腈中的酸/碱，光和Al 3+触发时，二芳基乙烯可用作多址荧光开关。当受碱刺激时，其闭环异构体的最大吸收量从560 nm红移到594 nm，颜色从紫色变成蓝色。当被酸诱导时，其开环异构体的发射强度提高了109倍，并且荧光颜色从深青色变为亮青色。此外，当被Al 3+触发时，其荧光强度显着增加。由于形成了1：2的金属/配体络合物，其发射峰从460 nm移至476 nm。此外，将其光和金属响应荧光行为应用于构建具有三个输入和一个输出的分子逻辑电路。
• A highly selective ratiometric fluorescent chemosensor for Hg2+ based on a new diarylethene with a stilbene-linked terpyridine unit
  作者：Shuhong Jing、Chunhong Zheng、Shouzhi Pu、Congbin Fan、Gang Liu

  DOI：10.1016/j.dyepig.2014.03.023

  日期：2014.8

  A novel asymmetrical diarylethene with a stilbene-linked terpyridine chromophore has been synthesized by Heck reaction. It exhibited effectively switchable fluorescence when triggered by UV/Vis and Hg2+/EDTA. Induced by Hg2+, its emission peak was red-shifted by 60 nm and emission intensity was enhanced by 4-fold with a concomitant color change from light blue to bright green due to the formation of a 1:2 metal/ligand complex. As a result, the diarylethene can serve as a fluorescence chemosensor for highly selective recognition of Hg2+ in dichloromethane. Moreover, a complicated logic circuit was constructed with the unimolecular platform by using the fluorescence intensity at 514 nm as outputs and the combinational stimuli of light and chemical species as inputs. (C) 2014 Elsevier Ltd. All rights reserved.
• A diarylethene derived Fe3+ fluorescent chemosensor and its application in wastewater analysis
  作者：Yongjie Li、Wenhao Pan、Chunhong Zheng、Shouzhi Pu

  DOI：10.1016/j.jphotochem.2019.112282

  日期：2020.2

  A diarylethylene derivative containing an acylhydrazone Schiff base moiety was designed and synthesized. Upon alternative irradiation with UV and visible lights, the compound showed distinct fluorescence switching properties based on fluorescence resonance energy transfer mechanism. On the other hand, the fluorescence can be efficiently quenched by 69 fold in the presence of Fe3+ ion in methanol. As a Fe3+ fluorescent chemosensor, the sensing mechanism, the influence of pH on sensing properties, and the practical application were also studied. In the complex, the breaking of the intramolecular H-bonding between the -CO = NH- proton and the oxygen at the C= O of lactone, the weaking of electrons transfer, and the paramagnetic nature of Fe3+ induced a consequent decrease fluorescence. The compound was found to be stable in a wide range of pH and a highly efficient Fe3+ ion quencher with a detection limit of 4.6 x 10(-6) mol L-1. Moreover, the fluorescent detection of Fe3+ was demonstrated by filter paper strips. A series of test papers with different Fe3+ concentrations were prepared and used as the standard card. The analytical application of measuring Fe3+ concentration in wastewater samples were evaluated by comparison with the standard card directly and quickly.
• A multiple switching diarylethene with a phenyl-linked rhodamine B unit and its application as chemosensor for Cu2+
  作者：Shouzhi Pu、Lele Ma、Gang Liu、Haichang Ding、Bing Chen

  DOI：10.1016/j.dyepig.2014.07.030

  日期：2015.2

  A new photochromic diarylethene with a phenyl-linked rhodamine B unit was synthesized and its photochemcial properties were systematically studied. The diarylethene could be used as a multiple fluorescence switch by sequential stimulations with protons and light. As a result, an INHIBIT logic gate was constructed by using the stimulation of trifluoroacetic acid and ultraviolet as inputs and the fluorescence intensity at 599 nm as output. Additionally, the diarylethene could act as a naked-eye chemosensor for the recognition of Cu2+ in aqueous acetonitrile. When triggered by Cu2+, the fluorescence intensity of the diarylethene at 594 nm was dramatically enhanced by 133-fold with a significant fluorescence change from dark to bright yellow. (C) 2014 Elsevier Ltd. All rights reserved.