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A Simple Oxindole-Based Colorimetric HSO4¯ Sensor Naked-Eye Detection and Spectroscopic Analysis

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A Simple Oxindole-Based Colorimetric HSO4¯ Sensor Naked-Eye Detection and Spectroscopic Analysis Journal of Photochemistry & Photobiology A: Chemistry 376 (2019) 146–154 Contents lists available at ScienceDirect Journal of Photochemistry & Photobiology A: Chemistry journal homepage: www.elsevier.com/locate/jphotochem A simple oxindole-based colorimetric HSO4¯ sensor: Naked-eye detection and spectroscopic analysis T ⁎ Sinan Bayindira, , Ferruh Lafzib a Department of Chemistry, Faculty of Sciences and Arts, Bingöl University, 12000, Bingöl, Turkey b Department of Chemistry, Faculty of Sciences, Atatürk University, 25240, Erzurum, Turkey ARTICLE INFO ABSTRACT Keywords: Detection of hydrogen sulfate from an aqueous organic solvent systems medium attracts to lots of interest be- Oxindole cause of could be in most environmental and biological systems. In this study, the simple receptors 5 and 6 Hydrogen sulfate containing oxindole core were synthesized, and the anion sensing properties were studied using colorimetric, Colorimetric fluorometric detection and 1H-NMR spectroscopy. The research indicated that the specific ligand affinity for 4,7-dihydroindole hydrogen sulfate ions results in drastic color and spectral changes. According to the data obtained, a new peak at Indole 371 nm in the absorption spectrum of 5 and an increase in fluorescence intensity of 5 were observed in the Turn-on sensor ¯ presence of HSO4 ions. The binding ratio of 5 to HSO4¯ was calculated to be 1:1 according to Job's plot ex- − periments. The Ks value was found to be 1.21×105 M 1 using the Benesi-Hildebrand equation. The LOD value ¯ was calculated with value as low as 8.9 μM for HSO4 . Moreover, DFT calculations confirmed the nonplanar structures or propeller structures. As a result of all these studies, it can be said that 5 which is non-toxic, may be a useful and selective candidate turn-on sensor for HSO4¯ sensing in the industrial wastewaters. 1. Introduction selectivity [18]. In recent years, oxindoles have received considerable attention from Ions play an essential role in many biological and chemical pro- synthetic organic chemists because of their technological properties cesses and the sensing of anions is often indispensable in environ- [19–21]. The researchers have focused on developing effective and mental, biological, and industrial research [1–3]. Therefore, the design innovative synthetic strategies because of their extraordinary biological and synthesis of chemosensors, which can selectively detect anions, are and photophysical properties [22–26]. One of these synthetic syntheses always of great interest in the research of anion sensing [4–6]. Syn- approach was developed by Bayindir and colleagues [27]. In this ap- thetic chemosensors, which selectively detect and bind some anions, proach the nucleophilic reactions of indole (2, Scheme S1) take place at especially F¯, AcO¯, HSO4¯ usually occur in hydrogen bonding units the C3 position, the nucleophilic reactions of 4,7-dihydro-1H-indole (3, such as indole, oxindole, pyrrole, urea, amine, and phenol (Fig. 1 and Scheme S1) obtained from the reduction of indole take place at the C2 Scheme 1)[7–10]. In recent studies, researchers have focused on the position [28,29]. Moreover, to date, many researchers synthesized synthesis of fluorescent and colorimetric receptors that do not require oxindole-based organic ligands and investigated the ion-sensing prop- expensive instruments for anion sensing. Colorimetric sensor materials erties [30–36]. are better because the signaling can be detected by the naked eye In our previous studies, we developed a facile protocol for preparing [11,12]. For anions, the detection of hydrogen sulfate is of great in- oxindole derivatives with the addition of one or two equivalent 4,7- terest because of its widespread role in industrial and biological fields. dihydro-1H-indole (3) using isatine (1) as an electrophile followed by This compound is found in materials such as agricultural fertilizers, oxidation [27]. In this study, the obtained molecules were evaluated in nuclear fuel waste, and industrial wastage, and may have severe con- terms of their abilities in anion sensing and recognition. The skeletons sequences as a toxic pollutant when it contaminates the environment of the oxindole derivatives not only act as color-reporting groups, but [13–16]. An improved, highly selective method for detecting hydrogen also provide an acidic H-bond donor and basic H-bond acceptor moi- sulfate ions is an important goal in chemosensor studies [17]. In only a eties for ion-binding. few cases have chemosensors shown absorbance changes upon the in- troduction of hydrogen sulfate, and these have been of debatable ⁎ Corresponding author. E-mail address: [email protected] (S. Bayindir). https://doi.org/10.1016/j.jphotochem.2019.03.011 Received 13 June 2018; Received in revised form 5 March 2019; Accepted 6 March 2019 Available online 07 March 2019 1010-6030/ © 2019 Elsevier B.V. All rights reserved. S. Bayindir and F. Lafzi Journal of Photochemistry & Photobiology A: Chemistry 376 (2019) 146–154 Fig. 1. Structures of the oxindole derivatives 5 and 6. Scheme 1. Plausible intermediates from the interaction between the receptor with hydrogen sulfate anions. 2. Experimental 2.2. Synthesis of oxindole-based probes 2.1. Material and apparatus The synthesis of 4,7-dihydro-1H-indole (3): The output compound 3 was prepared according to the literature method [10,27,37–39]. 1H- All chemicals, reagents, and solvents were commercially available NMR (400 MHz, CDCl3): δ 7.70 (m, NH, 1 H), 6.72 (t, J = 2.5 Hz, =CH, from Sigma-Aldrich or Merck. The ethanol-4-(2-hydroxyethyl) piper- 1 H), 6.07 (t, J = 2.5 Hz, =CH, 1 H), 5.95 (bd, J = 10.1 Hz, =CH, 13 azine-1-ethanesulfonic acid (HEPES) buffer (pH range 6.8–8.2) was 1 H), 5.87 (bd, J = 10.1 Hz, =CH, 1 H), 3.30 (bs, CH2, 4 H); C-N MR prepared by dissolving 2.38 g of pure HEPES in deionized water (100 MHz, CDCl3): δ 128.0, 127.9, 125.98, 118.3, 115.9, 108.8, 27.1, (100 mL) and adding one NaOH pellet to raise the pH towards 7.4. The 26.0. pH is modulated by adding 75% HClO4 or NaOH solution. Melting point The synthesis of 3-(4,7-dihydro-1H-indol-2-yl)-3-hydroxyindolin-2-one was determined on a Buchi 539 capillary melting apparatus and are (5): Probe 5 was prepared according to the literature method [27]. 1H- uncorrected. Infrared spectra were recorded on a Mattson 1000 FT-IR NMR (400 MHz, DMSO-d6): δ 10.42 (bs, NH, 1 H), 10.21 (s, NH, 1 H), spectrophotometer. 1H NMR and 13C NMR spectra were recorded on a 7.38 (d, J =7.6 Hz, =CH, 1 H), 7.20 (t, J =7.6 Hz, =CH, 1 H), 6.97 (t, 400 (100)-MHz Varian and Bruker spectrometer and are reported in J =7.6 Hz, =CH, 1 H), 6.79 (d, J =7.6 Hz, =CH, 1 H), 7.31 (s, =CH, terms of chemical shift (δ, ppm) with SiMe4 as an internal standard. 1 H), 5.77 (m, =CH, 2 H), 5.27 (d, J = 2.5 Hz, OH, 1 H), 3.30-3.27 (m, 1 13 Data for H NMR are recorded as follows: chemical shift (δ, ppm), CH2, 2 H), 3.17-3.13 (m, CH2, 2 H); C-N MR (100 MHz, DMSO-d6): δ multiplicity (s: singlet, d: doublet, t: triplet, q: quartet, p: pentet, m: 178.3, 142.2, 133.1, 129.6, 129.4, 126.0, 125.7, 125.6, 124.2, 122.2, multiplet, bs: broad singlet, bd: broad doublet, qd: quasi doublet) and 112.3, 110.2, 105.5, 74.1, 25.1, 24.6. coupling constant (s) in Hz, integration. Elemental analyses were car- The synthesis of 1H,1”H-[2,3':3',2”-terindol]-2'(1'H)-one (6): Probe 6 ried out on a LECO CHNS-932 instrument. Column chromatography was prepared according to the literature method [27]. 1H-NMR was carried out on silica gel 60 (230–400 mesh ASTM). The reaction (400 MHz, CDCl3): δ 8.76 (bs, NH, 2 H), 8.30 (bs, NH, 1 H), 7.60 (d, J progress was monitored by thin-layer chromatography (TLC) (0.25- =7.6 Hz, =CH, 1 H), 7.52 (d, J =7.6 Hz, =CH, 2 H), 7.33-7.26 (m, mm-thick precoated silica plates: Merck Fertigplatten Kieselgel (60 =CH, 3 H), 7.20-7.13 (m, =CH, 3 H), 7.06 (t, J =7.6 Hz, =CH, 2 H), F254)). UV–vis absorption and fluorescence spectra of samples were 6.99 (d, J =7.6 Hz, =CH, 1 H), 6.42 (s, =CH, 2 H); 13 C-N MR recorded on a Shimadzu UV-3101PL UV–vis-NIR spectrometer and (100 MHz, CDCl3): δ 177.0, 140.3, 136.8, 135.1, 130.8, 129.4, 128.0, Perkin–Elmer (Model LS 55) Fluorescence Spectrophotometer, respec- 126.1, 123.6, 122.7, 120.9, 120.4, 111.4, 110.9, 102.4, 79.3. tively. 2.3. UV–vis and fluorescence studies of 5 with various anions − The solution of oxindole derivative 5 (1 × 10 2 M) and anions 147 S. Bayindir and F. Lafzi Journal of Photochemistry & Photobiology A: Chemistry 376 (2019) 146–154 −2 (tetrabutylammonium salt, 1 × 10 M) were prepared in CH3CN/H2O (v/v: 7/3) with HEPES buffer solutions (pH 7.4). A solution of oxindole derivative 5 (5 × 10-6 M) was placed in a quartz cell and the UV–vis and fluorescence spectrums were recorded. After introduction of the solution of anions (1 equiv.), the changes in absorbance intensity were recorded at room temperature each time. As a result of pH studies, all measurements were carried out in CH3CN/H2O (v/v: 7:3) with HEPES buffer solutions (pH 7.4).
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