Synthesis of a new pyrene-devived fluorescent probe for the detection of Zn2

• Published in: Tetrahedron letters Vol. 59; no. 44; pp. 3916 - 3922
• Main Authors: Tang, Yanfeng, Huang, Yang, Lu, Linxia, Wang, Chun, Sun, Tongming, Zhu, Jinli, Zhu, Guohua, Pan, Jinyang, Jin, Yingli, Liu, Ailin, Wang, Miao
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 31.10.2018; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Live cells; Physical Sciences; Pyrene; Science & Technology; Turn-on fluorescence; Zn2+detection; Pyrene; Live cells; Turn-on fluorescence; Zn2+detection; HEAVY-METALS; ZN(II); SENSOR; IONS; TURN-ON CHEMOSENSOR; AQUEOUS-SOLUTION; HIGH-SENSITIVITY; SCHIFF-BASE; SELECTIVE DETECTION; LIVING CELLS
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2018.09.038

[Display omitted] •A novel pyrene-based fluorescence sensor for Zn2+ was designed and synthesized.•This sensor was of good selectivity and sensitivity for Zn2+ without the interference of Cd2+.•This sensor can be used in live cells. A novel pyrene-based receptor bearing benzothiazole was synthesized as a good turn-on fluorescent sensor for the recognition of Zn2+. The probe showed an excellent selectivity for Zn2+over most other competing ions (eg, Cr3+, Li+, Cd2+, Al3+, Pb2+, Li+, Mg2+, Ag+, Ca2+, Ni2+, Mn2+, Fe3+, Hg2+, Ba2+, K+, Na+, Cu2+, Fe2+) in EtOH-HEPES (65:35, v/v, pH = 7.20), which might be attributed to the photoinduced electron transfer (PET) mechanism. The formation of 1:1 stoichiometric PBZ-Zn2+ complex was determined based on the Job's plot, 1H NMR titration and ESI-MS. The binding constant of the complex was 4.04 × 104 M−1 with a detection limit of 2.58 × 10−7 M. The potential application of the PBZ in real water samples for recognizing Zn2+ was investigated. Bio-imaging study also revealed that PBZ could be applied to detecting Zn2+ in live cells. These results indicated that PBZ could be a favorable probe for Zn2+.