Novel Synthetic Approach towards Amino-Substituted Polycyclic Aromatic Hydrocarbons through Electrocyclization of Keteniminium Salts
Abstract
Polycyclic aromatic hydrocarbons (PAHs) are an important family of molecules in science and technology. Amino-substituted PAHs are promising building blocks to create attractive molecules for materials science. However, the synthetic limitations have hampered to produce diverse structures of amino-substituted PAHs. Here we describe a novel efficient synthetic method to access amino-substituted PAHs through the electrocyclization of highly reactive keteniminium species. We demonstrated the synthesis of various amino-substituted PAHs and disclosed some of their photophysical properties. Furthermore, combination with theoretical calculation revealed that the multiple electrocyclization reactions of keteniminium species is a stepwise process and the fusion of additional aromatic ring to the substrate accelerates the electrocyclization. Show more
Publication status
publishedExternal links
Journal / series
Helvetica Chimica ActaVolume
Pages / Article No.
Publisher
Wiley-VCHSubject
amino-substituted polycyclic aromatic hydrocarbons; electrocyclic reactions; fluorescence; keteniminium speciesMore
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