title: A simple naphthalene-based fluorescent probe for high selective detection of formaldehyde in toffees and HeLa cells via aza-Cope reaction.
abstract: A simple naphthalene-based fluorescent probe (AENO) for formaldehyde (FA) was successfully synthesized, which exhibited a significant fluorescence turn-on response towards FA in aqueous solution. The probe could quantitatively determine the concentration of FA (0-1.0mM) with excellent selectivity, high sensitivity and low limit of detection (0.57µM). The sensing mechanism was proposed as 2-aza-Cope rearrangement for AENO after reaction with FA, which was confirmed by (1)H NMR, HR-MS, FT-IR, UV-vis and fluorescence spectra. The probe has been employed to determine the FA contents in several commercially available toffee samples with satisfactory performance. Thus, AENO might be used as a promising tool for quantitative detection of FA in food. Furthermore, fluorescence imaging of HeLa cells indicated that the probe was cell membrane permeable and could be used for visualizing/imaging the FA trace/transportation in cancer cells.
authors: Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry & Chemical Engineering, Tianjin University of Technology, Tianjin, 300384 PR China.
authors: Junchao
authors: J
authors: Xu
authors: Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry & Chemical Engineering, Tianjin University of Technology, Tianjin, 300384 PR China.
authors: Yue
authors: Y
authors: Zhang
authors: Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry & Chemical Engineering, Tianjin University of Technology, Tianjin, 300384 PR China. Electronic address: zlt1981@126.com.
authors: Lintao
authors: L
authors: Zeng
authors: Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry & Chemical Engineering, Tianjin University of Technology, Tianjin, 300384 PR China.
authors: Jinbiao
authors: J
authors: Liu
authors: Department of Bioengineering, McGill University, 817 Sherbrook Street, Montreal, Quebec, Canada H3A0C3.
authors: Joseph M
authors: JM
authors: Kinsella
authors: Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032 PR China; Department of Chemistry, Université de Montréal, Succursale Centre-ville, Montreal, Quebec, Canada H3C3J7. Electronic address: rlsheng@mail.sioc.ac.cn.
authors: Ruilong
authors: R
authors: Sheng
mesh_terms: D001372:Aza Compounds / Q000737:chemistry; D002182:Candy / Q000032:analysis; D005456:Fluorescent Dyes / Q000737:chemistry*; D005506:Food Contamination / Q000032:analysis; D005557:Formaldehyde / Q000032:analysis* / Q000737:chemistry; D006367:HeLa Cells; D006801:Humans; D057230:Limit of Detection; D009281:Naphthalenes / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D001372:Aza Compounds; D005456:Fluorescent Dyes; D009281:Naphthalenes; D005557:Formaldehyde
keywords: Aza-Cope rearrangement; Cell imaging; Fluorescent probe; Formaldehyde; Toffee samples