bis(2-[6-(diethylcarbamoyl)-4-[(4-isothiocyanatophenyl)ethynyl]pyridin-2-yl]-1-ethylbenzimidazol-5-yl)methane | 479670-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: bis(2-[6-(diethylcarbamoyl)-4-[(4-isothiocyanatophenyl)ethynyl]pyridin-2-yl]-1-ethylbenzimidazol-5-yl)methane
• 英文别名: bis(2-[6-(diethylcarbamoyl)-4-[(4-isothiocyanatophenyl)ethynyl]pyridine-2'-yl]-1-ethylbenzimidazol-5-yl)methane；6-[5-[[2-[6-(diethylcarbamoyl)-4-[2-(4-isothiocyanatophenyl)ethynyl]pyridin-2-yl]-1-ethylbenzimidazol-5-yl]methyl]-1-ethylbenzimidazol-2-yl]-N,N-diethyl-4-[2-(4-isothiocyanatophenyl)ethynyl]pyridine-2-carboxamide
• CAS: 479670-00-3
• 化学式: C₅₇H₅₀N₁₀O₂S₂
• 分子量: 971.222
• InChiKey: JCVXOXWJJNPUNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.6
• 重原子数：
  71
• 可旋转键数：
  18
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  191
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  lanthanum(III) perchlorate hydrate 、 bis(2-[6-(diethylcarbamoyl)-4-[(4-isothiocyanatophenyl)ethynyl]pyridin-2-yl]-1-ethylbenzimidazol-5-yl)methane 以 乙腈 为溶剂， 以65%的产率得到La2(bis(2-[6-diethylcarbamoyl)-4-[(4-isothiocyanatophenyl)ethynyl]pyridin-2'-yl-1-ethylbenzimidazol-5-yl)methane)3 perchlorate
  参考文献：
  名称：

  Self-Assembled Triple-Stranded Lanthanide Dimetallic Helicates with a Ditopic Ligand Derived from Bis(benzimidazole)pyridine and Featuring an (4-Isothiocyanatophenyl)ethynyl Substituent

  摘要：

  Bis(2-{6-(diethylcarbamoyl)-4-[(4-isothiocyanatophenyl)ethynyl]pyridin-2'-yl}-1-ethylbenzimidazol-5-yl)methane (L-G) reacts with trivalent lanthanide ions in acetonitrile to yield triple-stranded dimetallic helicates [Ln(2)(L-G)(3)](6+). H-1-NMR Data point to the helicates being the only species formed under stoichiometric conditions and having a time-averaged D-3 symmetry on the NMR time scale. The photophysical properties of L-G and its helicates are discussed with respect to the closely related ligands L-B, L-E, and their complexes, two ligands devoid of the isothiocyanatophenylethynyl substituent. ne quantum yield of the ligand fluorescence is three times smaller compared to L-E, while that of the Eu(III)centered luminescence (1.1%) is three times larger. On the other hand, the luminescence of Tb-III is not sensitized by L-G. This is explained in terms of energy differences between the singlet and triplet states on one hand, and between the 0-phonon transition of the triplet state and the excited metal ion states on the other. This work demonstrates that bulky substituents in the 4-position of the pyridine ring do not prevent the formation of triple-stranded helicates, opening the way for luminescent probes that can easily be coupled to biological materials.

  DOI：

  10.1002/1522-2675(200207)85:7<1915::aid-hlca1915>3.0.co;2-n
• 作为产物：
  描述：

  二吡啶硫碳酸酯 、 bis(2-[6-(diethylcarbamoyl)-4-[(4-aminophenyl)ethynyl]pyridin-2-yl]-1-ethylbenzimidazol-5-yl)methane 以 二氯甲烷 为溶剂， 反应 3.0h， 以98%的产率得到bis(2-[6-(diethylcarbamoyl)-4-[(4-isothiocyanatophenyl)ethynyl]pyridin-2-yl]-1-ethylbenzimidazol-5-yl)methane
  参考文献：
  名称：

  Self-Assembled Triple-Stranded Lanthanide Dimetallic Helicates with a Ditopic Ligand Derived from Bis(benzimidazole)pyridine and Featuring an (4-Isothiocyanatophenyl)ethynyl Substituent

  摘要：

  Bis(2-{6-(diethylcarbamoyl)-4-[(4-isothiocyanatophenyl)ethynyl]pyridin-2'-yl}-1-ethylbenzimidazol-5-yl)methane (L-G) reacts with trivalent lanthanide ions in acetonitrile to yield triple-stranded dimetallic helicates [Ln(2)(L-G)(3)](6+). H-1-NMR Data point to the helicates being the only species formed under stoichiometric conditions and having a time-averaged D-3 symmetry on the NMR time scale. The photophysical properties of L-G and its helicates are discussed with respect to the closely related ligands L-B, L-E, and their complexes, two ligands devoid of the isothiocyanatophenylethynyl substituent. ne quantum yield of the ligand fluorescence is three times smaller compared to L-E, while that of the Eu(III)centered luminescence (1.1%) is three times larger. On the other hand, the luminescence of Tb-III is not sensitized by L-G. This is explained in terms of energy differences between the singlet and triplet states on one hand, and between the 0-phonon transition of the triplet state and the excited metal ion states on the other. This work demonstrates that bulky substituents in the 4-position of the pyridine ring do not prevent the formation of triple-stranded helicates, opening the way for luminescent probes that can easily be coupled to biological materials.

  DOI：

  10.1002/1522-2675(200207)85:7<1915::aid-hlca1915>3.0.co;2-n