N-methyl-4,5-bis[2,5-dimethyl-3-thienyl]-2-(2-pyridyl)imidazole | 940934-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-methyl-4,5-bis[2,5-dimethyl-3-thienyl]-2-(2-pyridyl)imidazole
• 英文别名: 2-pyridyl-4,5-bis(2,5-dimethyl(3-thienyl))-1-methylimidazole；2-[4,5-bis(2,5-dimethylthiophen-3-yl)-1-methylimidazol-2-yl]pyridine
• CAS: 940934-39-4
• 化学式: C₂₁H₂₁N₃S₂
• 分子量: 379.55
• InChiKey: BEZGKCMSSHPVJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  87.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methyl-4,5-bis[2,5-dimethyl-3-thienyl]-2-(2-pyridyl)imidazole 、 五羰基氯铼(I) 以 苯 为溶剂， 生成
  参考文献：
  名称：

  Metal Coordination-Assisted Near-Infrared Photochromic Behavior:  A Large Perturbation on Absorption Wavelength Properties of N,N-Donor Ligands Containing Diarylethene Derivatives by Coordination to the Rhenium(I) Metal Center

  摘要：

  A new series of diarylethene-containing 1-aryl-substituted 2-(2-pyridyl)imidazole (L) ligands have been prepared and characterized. Subsequent reactions of the 2-(2-pyridyl)imidazole ligands with Re(CO)(5)Cl under reflux conditions afforded [Re(CO)(3)(L)Cl]; one of the complexes has also been structurally determined. The open forms of the ligands showed an intense absorption band at ca. 320 nm corresponding to pi -> pi* and n -> pi* transitions of the 1-aryl-2-(2-pyridyl)imidazole moiety, with mixing of pi -> pi* and n -> pi* transitions of the thiophene moieties. The corresponding rhenium(I) complexes showed IL absorption bands at ca. 352 nm, with additional MLCT [d pi(Re) -> pi*(L)] transitions at ca. 425 nm. Upon photocyclization of the diarylethene moieties by UV irradiation, two new absorption bands emerged at ca. 410-425 and 576-586 nm for the ligands, while the rhenium(I) complexes showed three new absorption bands at ca. 288-290, 475-480, and 712-713 nm upon excitation into either the IL or MLCT bands. Such a large shift of the absorption bands of the closed forms of the rhenium(I) complexes to the NIR region could be attributed to the planarization of the four heterocyclic rings relative to the open forms. On the contrary, the organic ligand systems alone did not display such a shift of the absorption maxima to the NIR region upon photocyclization.

  DOI：

  10.1021/ja067425r
• 作为产物：
  描述：

  、 2,5-二甲基噻吩-3-硼酸 在 四(三苯基膦)钯 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 以60%的产率得到N-methyl-4,5-bis[2,5-dimethyl-3-thienyl]-2-(2-pyridyl)imidazole
  参考文献：
  名称：

  Metal Coordination-Assisted Near-Infrared Photochromic Behavior:  A Large Perturbation on Absorption Wavelength Properties of N,N-Donor Ligands Containing Diarylethene Derivatives by Coordination to the Rhenium(I) Metal Center

  摘要：

  A new series of diarylethene-containing 1-aryl-substituted 2-(2-pyridyl)imidazole (L) ligands have been prepared and characterized. Subsequent reactions of the 2-(2-pyridyl)imidazole ligands with Re(CO)(5)Cl under reflux conditions afforded [Re(CO)(3)(L)Cl]; one of the complexes has also been structurally determined. The open forms of the ligands showed an intense absorption band at ca. 320 nm corresponding to pi -> pi* and n -> pi* transitions of the 1-aryl-2-(2-pyridyl)imidazole moiety, with mixing of pi -> pi* and n -> pi* transitions of the thiophene moieties. The corresponding rhenium(I) complexes showed IL absorption bands at ca. 352 nm, with additional MLCT [d pi(Re) -> pi*(L)] transitions at ca. 425 nm. Upon photocyclization of the diarylethene moieties by UV irradiation, two new absorption bands emerged at ca. 410-425 and 576-586 nm for the ligands, while the rhenium(I) complexes showed three new absorption bands at ca. 288-290, 475-480, and 712-713 nm upon excitation into either the IL or MLCT bands. Such a large shift of the absorption bands of the closed forms of the rhenium(I) complexes to the NIR region could be attributed to the planarization of the four heterocyclic rings relative to the open forms. On the contrary, the organic ligand systems alone did not display such a shift of the absorption maxima to the NIR region upon photocyclization.

  DOI：

  10.1021/ja067425r

文献信息

• Two cyclometalated Pt(<scp>ii</scp>) complexes showing reversible phosphorescence switching due to grinding-induced destruction and crystallization-induced formation of supramolecular dimer structure
  作者：Qin-Zhen Yuan、Fu-Shun Wan、Ting-Ting Shen、Deng-Ke Cao

  DOI：10.1039/d1ra07142d

  日期：——

  Complexes [Pt(dfppy)(pbdtmi)]PF6 (1) and [Pt(ppy)(pbdtmi)]PF6 (2) have been constructed based on dithienylethene-based N^N ligand pbdtmi, showing supramolecular dimer structure in which two coordination cations connect each other through π⋯π stacking interaction. The crystalline state samples of both 1 and 2 reveal strong phosphorescence (emission peak: around 579 nm for 1, and 551 nm for 2). Interestingly

  [Pt(dfppy)(pbdtmi)]PF 6 ( 1 ) 和 [Pt(ppy)(pbdtmi)]PF 6 ( 2 ) 基于二噻吩基乙烯 N^N 配体 pbdtmi 构建，呈现出超分子二聚体结构，其中两个配位阳离子通过π⋯π堆积作用相互连接。1和2的晶态样品均显示出强磷光（发射峰：1约为 579 nm， 2约为551 nm ）。有趣的是，对1或2进行研磨处理导致磷光从开启状态切换到关闭状态。随后用甲苯结晶恢复初始开启状态。这项工作讨论了超分子二聚体结构与1和2中相关的磷光转换行为之间的关系，并探讨了pbdtmi、1和2的光致变色。