Colorimetric and fluorimetric sensing of trace amount of Hg2+ in real samples by a new rhodamine B-based Schiff base probe: Smartphone, living cell applications and DFT calculation

• Published in: Journal of molecular structure 2025-02, Vol.1321, p.139687, Article 139687
• Main Authors: Ejder, Nebahat, Karaoglu, Kaan, Levent, Zeynep, Alcay, Yusuf, Ozdemir, Emre, Yavuz, Ozgur, Kaya, Kerem, Kopar, Merve, Tuzun, Nurcan Şenyurt, Yilmaz, Ismail
• Format: Article
• Language: English
• Subjects: DFT Calculation; Fluorescent probe; Rhodamine B derivative; Sensing mercury ion; Smartphone and living cell applications
• ISSN: 0022-2860
• DOI: 10.1016/j.molstruc.2024.139687

•A new xanthene-based Schiff base probe was synthesized and utilized for highly selective and sensitive quantification of Hg2+.•A smartphone technique was quickly applied to analyze Hg2+ in real samples with good recovery rates.•3-Dimensional geometries and the electronic properties of the probe and (3), 3-Hg and hydrolysis product were explained by DFT calculations.•The probe exhibited a high potential for Hg2+ sensing on adenocarcinoma alveolar basal epithelial (A549) cancer cells. In this study, a Schiff base-based probe, named as 2-((methyl benzoate-4-yl)methyleneamino)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthene]-3-one (2), was successfully synthesized and characterized by various spectral techniques besides single-crystal x-ray diffraction. The investigation was focused on the analyzing the selectivity of the probe towards some common metal ions. The study was conducted in an aqueous medium, and the results indicated that the probe showed high selectivity towards the Hg2+ ion. The utilization of mass analysis revealed that the optical emission originating from rhodamine ethyl ester can be generated through the spirolactam ring/Schiff base hydrolysis facilitated by the Hg2+ ion. The Limit of Detection (LOD) for the Hg2+ ions by colorimetry and fluorometry were determined to be 3.0 × 10-8 M and 9.4 × 10-9 M, respectively. A technique using a smartphone was quickly applied to analyze Hg2+ in real samples with good recovery rates (96.5%-101.5%). To explain their 3-dimensional geometries and the electronic properties, the DFT calculations were also performed on 2, its spiro bond opened Hg-complex (3-Hg), Hg2+ uncomplexed product (3) and the rhodamine ethyl ester hydrolysis product. Moreover, mercury detection potency of the probe at the cellular level was investigated on adenocarcinoma alveolar basal epithelial (A549) cancer cells, and the result showed that the probe exhibits high potential for living cell imaging. [Display omitted]