Nitrogen-doped polycyclic aromatic hydrocarbons by a one-pot Suzuki coupling/intramolecular S N Ar reaction.
Xiaoqi TianKazutaka ShoyamaFrank WürthnerPublished in: Chemical science (2022)
We report a new method for the synthesis of nitrogen-doped (N-doped) polycyclic aromatic hydrocarbons (PAHs) by a Suzuki coupling/intramolecular S N Ar cascade reaction. A one- or two-fold [3 + 3] naphtho-annulation of halogenated aniline was conducted under Suzuki-Miyaura cross-coupling conditions to yield a series of fully fused N-doped PAHs. In contrast to reported methods to synthesize pyridinic or pyrrolic nitrogen-doped PAHs, our method enables preparation of PAHs doped with graphitic nitrogen, for which few reports are known in the literature. The crystal structure as well as absorption, fluorescence and electrochemical properties of these N-doped PAHs were investigated, which demonstrated the capability of N-doping to adjust optical and electronic properties and alter the LUMO energy level.
Keyphrases
- polycyclic aromatic hydrocarbons
- quantum dots
- visible light
- crystal structure
- energy transfer
- highly efficient
- metal organic framework
- systematic review
- room temperature
- electron transfer
- high resolution
- magnetic resonance
- gold nanoparticles
- molecularly imprinted
- emergency department
- high speed
- ionic liquid
- risk assessment
- mass spectrometry
- single molecule
- contrast enhanced
- climate change
- human health