Abstract
Naphthalimide–benzothiazole conjugate (NBTZ) linked by cinnamonitrile was designed, synthesized, and fully characterized by NMR (1H, 13C, DEPT, HSQC) and high-resolution mass spectrometry. NBTZ exhibited unique turn-on fluorescence in the presence of CN− with relatively high selectivity compared to other anions such as SCN−, HSO4−, ClO4−, NO3−, Cl−, Br−, I−, and PO4−3 in tetrahydrofuran (THF). The detection limit for CN− was found to be 3.35 × 10−8 M in THF. The sensing mechanism was analyzed through 1H, 13C, DEPT, and mass spectroscopy. NBTZ also showed two-mode aggregation-induced emission (AIE) in THF–H2O mixtures. In a 30:70 THF–H2O (v/v) mixture, the maximum AIE was observed at 430 nm (blue) because of the rotation of the CC bond between the naphthalimide ring and the phenyl ring was restricted. In 10:90 THF–H2O (v/v), a new red-shifted AIE appeared at 490 nm (cyan), due to the extended π-conjugation induced by restriction of rotation of the CC bond between the benzothiazole and naphthalimide rings.
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