6-(1,3-二氢-2H-萘并[1,2-d]咪唑-2-亚基)环己-2,4-二烯-1-酮 | 14313-47-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 6-(1,3-二氢-2H-萘并[1,2-d]咪唑-2-亚基)环己-2,4-二烯-1-酮
• 英文名称: 2-(2-Hydroxyphenyl)-napht<1,2-d>imidazol
• 英文别名: 2-(1(3)H-naphtho[1,2-d]imidazol-2-yl)-phenol；2-(1(3)H-naphth[1,2-d]imidazol-2-yl)-phenol；2-(3H-benzo[e]benzimidazol-2-yl)phenol
• CAS: 14313-47-4
• 化学式: C₁₇H₁₂N₂O
• 分子量: 260.295
• InChiKey: KHVHNHQFFZSCTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 磷化氢 、 氢碘酸 作用下， 生成 6-(1,3-二氢-2H-萘并[1,2-d]咪唑-2-亚基)环己-2,4-二烯-1-酮
  参考文献：
  名称：

  Fischer,O., Journal fur praktische Chemie (Leipzig 1954), 1924, vol. <2> 107, p. 31

  摘要：

  DOI：

文献信息

• Recognition‐Induced Enhanced Emission of Core‐Fluorescent ESIPT‐type Macrocycles
  作者：Paulina Jurek、Hanna Jędrzejewska、Michał F. Rode、Agnieszka Szumna

  DOI：10.1002/chem.202203116

  日期：2023.1.9

  AbstractCore‐fluorescent cavitands based on 2‐(2′‐resorcinol)benzimidazole fluorophores (RBIs) merged with the resorcin[4]arene skeleton were designed and synthesized. The cavitands, due to the presence of intramolecular hydrogen bonds and increased acidity, show excited state intramolecular proton transfer (ESIPT) and readily undergo deprotonation to form dianionic cavitands, capable of strong binding to organic cations. The changes in fluorescence are induced by deprotonation and binding events and involve huge Stokes shifts (due to emission from anionic double keto tautomers) and cation‐selective enhancement of emission originating from the restriction of intramolecular motion (RIR) upon recognition in the cavity. Ab initio calculations indicate that the macrocyclic scaffold stabilizes the ground state tautomeric forms of the fluorophores that are not observed for non‐macrocyclic analogs. In the excited state, the emitting forms for both macrocyclic scaffolds and non‐macrocyclic analogs are anionic double keto tautomers, which are the result of excited state intramolecular proton transfer (ESIPT) or excited state double proton transfer (ESDPT).
• Fischer,O., Journal fur praktische Chemie (Leipzig 1954), 1924, vol. <2> 107, p. 31
  作者：Fischer,O.

  DOI：——

  日期：——