A Poly(carbazole-alt-triazole) with Thiabendazole Side Groups as an "On-Off-On" Fluorescent Probe for Detection of Cu(II) Ion and Cysteine.

Abstract

A novel conjugated polymer PCZBTA-TBZ containing thiabendazole as recognition unit was synthesized via Suzuki coupling reaction, and its structural characterization, spectroscopic analysis and photophysical properties were investigated. In the metal ion response study, the addition of Cu2+ led to the occurrence of the photoinduced electron transfer (PET) mechanism, which significantly quenched the fluorescence of the polymer PCZBTA-TBZ with a quenching effect of 98%. Furthermore, I- can significantly quench the fluorescence of the polymer, but other anions have no such effect. According to the density functional theory calculation, compared with other polycarbazoles or other alternative copolymers containing carbazole, with alternating carbazole and triazole enhances the electron mobility and reduces the energy band gap of the polymer. Due to the strong coordination ability between Cu2+ and Cys, the adding Cys competes the Cu2+ in the [PCZBTA-TBZ-Cu2+] complex, blocking the occurrence of PET, and the fluorescence intensity of PCZBTA-TBZ is restored. The addition of other amino acids caused almost no change. The polymer is expected to be used for dual fluorescence detection of specific metal ions and Cys.