Novel Synthetic Approach towards Amino-Substituted Polycyclic Aromatic Hydrocarbons through Electrocyclization of Keteniminium Salts

• Published in: Helvetica chimica acta Vol. 106; no. 9
• Main Authors: Yoshimura, Masahiko, Quinodoz, Pierre, Reyes Mendez, Lucia, Kolleth, Amandine, Sulzer-Mosse, Sarah, Vent-Schmidt, Thomas, Karadeniz Yezer, Ulfet, Catak, Saron, De Mesmaeker, Alain
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 01.09.2023; Wiley Subscription Services, Inc
• Subjects: Aromatic compounds; Chemistry; Chemistry, Multidisciplinary; Materials science; Physical Sciences; Polycyclic aromatic hydrocarbons; Science & Technology; Substitutes; Substrates; INTRAMOLECULAR 2+2 CYCLOADDITION; DENSITY FUNCTIONALS; fluorescence; ANALOGS; amino-substituted polycyclic aromatic hydrocarbons; RINGS; keteniminium species; REACTIVITY; IONS; electrocyclic reactions; DERIVATIVES; ACCESS
• ISSN: 0018-019X; 1522-2675
• DOI: 10.1002/hlca.202300085

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.