Novel Synthetic Approach towards Amino-Substituted Polycyclic Aromatic Hydrocarbons through Electrocyclization of Keteniminium Salts
Helvetica Chimica Acta, cilt.106, sa.9, 2023 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 106 Sayı: 9
- Basım Tarihi: 2023
- Doi Numarası: 10.1002/hlca.202300085
- Dergi Adı: Helvetica Chimica Acta
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Agricultural & Environmental Science Database, Applied Science & Technology Source, Aquatic Science & Fisheries Abstracts (ASFA), Biotechnology Research Abstracts, CAB Abstracts, Chemical Abstracts Core, Chimica, Compendex, EMBASE, Veterinary Science Database, DIALNET
- Anahtar Kelimeler: amino-substituted polycyclic aromatic hydrocarbons, electrocyclic reactions, fluorescence, keteniminium species
- Boğaziçi Üniversitesi Adresli: Evet
Özet
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.