BN-Embedded Polycyclic Aromatic Hydrocarbon Oligomers: Synthesis, Aromaticity, and Reactivity.
Yijing ChenWeinan ChenYanjun QiaoXuefeng LuGang ZhouPublished in: Angewandte Chemie (International ed. in English) (2020)
BN-embedded oligomers with different pairs of BN units were synthesized by electrophilic borylation. Up to four pairs of BN units were incorporated in the large polycyclic aromatic hydrocarbons (PAHs). Their geometric, photophysical, electrochemical, and Lewis acidic properties were investigated by X-ray crystallography, optical spectroscopy, and cyclic voltammetry. The B-N bonds show delocalized double-bond characteristics and the conjugation can be extended through the trans-orientated aromatic azaborine units. Calculations reveal the relatively lower aromaticity for the inner azaborine rings in the BN-embedded PAH oligomers. The frontier orbitals of the longer oligomers are delocalized over the inner aromatic rings. Consequently, the inner moieties of the BN-embedded PAH oligomers are more active than the outer parts. This is confirmed by a simple oxidation reaction, which has significant effects on the aromaticity and the intramolecular charge-transfer interactions.
Keyphrases
- polycyclic aromatic hydrocarbons
- high resolution
- amino acid
- density functional theory
- ionic liquid
- nitric oxide
- gene expression
- heavy metals
- molecular dynamics simulations
- molecular dynamics
- electron transfer
- single cell
- computed tomography
- mass spectrometry
- high speed
- human health
- atomic force microscopy
- health risk assessment
- magnetic resonance
- liquid chromatography