A highly selective naked-eye and fluorescent probe for fluoride ion based on 1,8-naphalimide and benzothizazole

• Published in: Dyes and pigments 2017-06, Vol.141, p.299-305
• Main Authors: Chen, Xiaoxing, Leng, Taohua, Wang, Chengyun, Shen, Yongjia, Zhu, Weihong
• Format: Article
• Language: English
• Subjects: 1, 8-Napthalimide; Benzothizazole; Fluorescent probe; Fluoride ion
• ISSN: 0143-7208; 1873-3743
• DOI: 10.1016/j.dyepig.2017.02.008

Based on benzothizazole and 1,8-naphalimide, a novel colorimetric and fluorescent probe (probe 1) for fluoride ion was synthesized by Schiff base reaction. The striking yellow-to-blue color change of the probe 1 in the CH3CN was observed with the naked eyes only in presence of F− among the eight anions (F−, Cl−, Br−, I−, NO3−, HSO4−, H2PO4−, AcO−). Besides that, upon addition of F−, both of the absorption and emission peaks shifted to near-infrared region (NIR) (>600 nm) in UV–vis and fluorescent spectra, and the detection limit reached as low as 0.41 μM. Furthermore, the 1H NMR titration and theoretical calculation based on TD-DFT indicated that the fluoride ion induced deprotonation of the probe 1 through hydrogen bonding interaction between amino group of probe 1 and fluoride ion. A novel near-infrared fluorescent probe with high sensitivity and selectivity for fluoride ion has been fabricated. [Display omitted] •The obvious color and fluorescence changes can be observed with naked eyes.•Probe 1 possesses good selectivity, low detection limit and fast response for F−.•Probe 1 displays ratiometric optical response to F− in near-infrared (NIR) region.