(5Z)-5-(4-ethynylbenzylidene)-1,3-thiazolidine-2,4-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (5Z)-5-(4-ethynylbenzylidene)-1,3-thiazolidine-2,4-dione
• 英文别名: (5Z)-5-[(4-ethynylphenyl)methylidene]-1,3-thiazolidine-2,4-dione
• 化学式: C₁₂H₇NO₂S
• 分子量: 229.259
• InChiKey: CIZRZQYTUWAKBB-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [RuCl(dppe)2]OTf 、 (5Z)-5-(4-ethynylbenzylidene)-1,3-thiazolidine-2,4-dione 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 [RuCl(dppe)2(CCHC6H4CHC3O2SNH)]OTf
  参考文献：
  名称：

  Alkynyl Ruthenium Colorimetric Sensors:  Optimizing the Selectivity toward Fluoride Anion

  摘要：

  We report on the synthesis of alkynyl ruthenium colorimetric sensors whose receptors are constituted by thiazolidinedione, rhodanine, or barbituric heads as recognition centers for anions. As modifications in the charge density at these recognition centers affect the whole molecule, through the alkynyl ligand acting as a communicating wire, the effects of hydrogen-bonding interactions with the anions were observed with the naked eye and monitored by UV-vis absorption spectrometry. The selectivity of the sensors was improved through electronic modifications of the alkynyl ruthenium subunit: the higher the electron density at the receptor head, the higher the selectivity is. TD-DFT calculations rationalize the long-range electronic communication as a main characteristic of the alkynyl ruthenium species and as a key to improve the selectivity of alkynyl ruthenium-based sensors toward anions.

  DOI：

  10.1021/ic062389i
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 4-乙炔基苯甲醛 在 ammonium acetate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 0.75h， 以73%的产率得到(5Z)-5-(4-ethynylbenzylidene)-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  通过炔基钌外表受体裸眼检测阴离子：选择性识别氟化物阴离子。

  摘要：

  带有末端氢键受体的炔基钌络合物可作为有效的阴离子传感器，表现出大的客体诱导的颜色变化，并且对氟离子表现出出乎意料的高选择性。

  DOI：

  10.1039/b503698d

文献信息

• Alkynyl Ruthenium Colorimetric Sensors:  Optimizing the Selectivity toward Fluoride Anion
  作者：Jean-Luc Fillaut、Julien Andriès、Johann Perruchon、Jean-Pierre Desvergne、Loïc Toupet、Lotfi Fadel、Bachir Zouchoune、Jean-Yves Saillard

  DOI：10.1021/ic062389i

  日期：2007.7.1

  We report on the synthesis of alkynyl ruthenium colorimetric sensors whose receptors are constituted by thiazolidinedione, rhodanine, or barbituric heads as recognition centers for anions. As modifications in the charge density at these recognition centers affect the whole molecule, through the alkynyl ligand acting as a communicating wire, the effects of hydrogen-bonding interactions with the anions were observed with the naked eye and monitored by UV-vis absorption spectrometry. The selectivity of the sensors was improved through electronic modifications of the alkynyl ruthenium subunit: the higher the electron density at the receptor head, the higher the selectivity is. TD-DFT calculations rationalize the long-range electronic communication as a main characteristic of the alkynyl ruthenium species and as a key to improve the selectivity of alkynyl ruthenium-based sensors toward anions.
• Naked eye detection of anions by alkynyl-ruthenium exo-receptors: selective recognition of fluoride anion
  作者：Jean-Luc Fillaut、Julien Andriès、Loïc Toupet、Jean-Pierre Desvergne

  DOI：10.1039/b503698d

  日期：——

  Alkynyl-ruthenium complexes bearing terminal hydrogen-bonding receptors act as efficient anion sensors exhibiting large guest-induced colour changes and show unexpectedly high selectivity to fluoride ions.

  带有末端氢键受体的炔基钌络合物可作为有效的阴离子传感器，表现出大的客体诱导的颜色变化，并且对氟离子表现出出乎意料的高选择性。