Naphthoquinone-Dopamine Linked Colorimetric and Fluorescence Chemosensor for Selective Detection of Sn²⁺ Ion in Aqueous Medium and Its Bio-Imaging Applications

Abstract

A simple naphthoquinone−dopamine hybrid (2CND) was designed and fabricated as a colorimetric and fluorescence chemosensor for the selective recognition of Sn 2+ in the aqueous medium. This simply accessible chemosensor was prepared by connecting of naphthoquinone acceptor and dopamine donor moieties via Michael-like addition reaction. The chemosensor 2CND showed a turn-on fluorescence response which operated through the inhibited photoinduced electron transfer effect. The sensor probe shows remarkable performance, such as high selectivity, sensitivity, excellent water solubility, and rapid response to Sn 2+ (less than 5 s). The detection mechanism of the 2CND−Sn 2+ complex was supported by FT-IR analysis, 1 H NMR titration, and DFT calculations. Besides, the 1:1 binding stoichiometry was confirmed by the ESI-MS spectral analysis. Furthermore, the chemosensor 2CND has been successfully employed as a fluorescence probe to monitor trace Sn 2+ in live cells and zebrafish. The sensor probe 2CND could serve as an effective fluorescence bioimaging probe for the discriminative detection of diseased and normal human cells.

Structure-Property Relationship in Selected Naphtho- and Anthra-Quinone Derivatives on the Basis of Density Functional Theory and Car–Parrinello Molecular Dynamics

“…The anthraquinone oligomers were reported as anode-active materials [17] in rechargeable nickel/oligomer batteries. In addition, naphthoquinone derivatives were found as colorimetric and fluorescence chemosensors for the selective recognition of Sn 2+ in an aqueous medium [18]. The examples mentioned above show how important and interesting from diverse points of view naphtho-and anthra-quinone derivatives are.…”

Synthesis and Characterization of Antioxidant Biphenyl Appended 1,2,3‐Triazoles as Potential Chemo‐Sensor for Sn2+ Ions: Excellent Selectivity and Low Detection Limit

“…The singlet at δ 5.60-5.64 ppm due to OÀ CH 2 further confirmed the formation of the cyclized product. The 13 C NMR of all the compounds (4 a-4 d) showed δ value in the range of 189.59-190.99 ppm corresponding to aldehydic carbon (CHO). The triazole carbon peaks appear in the region of δ 121.39-126.75 ppm.…”

“…Supporting Information contains 1 H NMR, 13 C NMR, Mass spectra of compounds 4(a-d), IR and 1 H NMR spectra of 4 a-Sn 2 + complex and Experiment details for the synthesis of compounds 4(a-d)…”

“…[12] The liver, brain, adrenal glands, thyroid gland, and spleen contains highest amount of tin. [13][14] Tin (II) as a chloride, fluoride or citrate complex is present in several consumables such as dental care products, soft drinks and food stuffs. [15,16] Sn(II) deficiency can cause serious issues in humans such as loss of hearing, breathing trouble and cause DNA damage.…”

A New Azo Dye Based Sensor for Selective and Sensitive Detection of Cu(II), Sn(II), and Al(III) Ions

“…26 Sn 2+ ions, are found in the thyroid gland, liver, spleen, brain, etc. 27,28 Sn 2+ also play important role for checking cancer and hair growth. Deficiency of Sn 2+ may lead to shortness of breath, dhearing problems and decreased haemoglobin production.…”