Preparation and ionophoric properties of coronene fluoroionophores containing azacrown and calix[4]azacrown ethers

Novel coronene fluoroionophores, N,N′-dipropyl-5,11-bis[4-(1-aza-18-crown-6)phenyl]cornene-2,3,8,9-tetracarboxy diimide (4), and N,N′-dipropyl-5,11-bis[4-(calix[4]azacrown-5-crown-5)phenyl]coronene-2,3,8,9-tetracarboxy diimide (6), were prepared by reacting N,N′-dipropyl-5,11-bis(p-chlorophenyl)coronene-2,3,8,9-tetracarboxy diimide (3) with 1-aza-18-crown-6 or calix[4] azacrown-5-crown-5. Alternating copolymers, 5 and 7, with a similar repeating unit were prepared by reacting 7,16-diaza-18-crown-6 or calix[4]bisazacrown-5 with compound 3. The fluoroionophoric characteristics were investigated by binding alkali, alkali earth metal and various metal ions. The model and polymeric fluoroionophores exhibited significant decreasing fluorescence effects with K+, Ag+ and Ba2+, which were attributed to photoinduced charge transfer (PCT).