Novel triazine-based colorimetric and fluorescent sensor for highly selective detection of Al3+

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The complexation activity of NADO with various metal ions in an ethanolic solution is specifically studied by means of fluorescent spectra. The NADO exhibits a significant fluorescence enhancement at 469 nm in presence of Al3 þ due to the formation of a complex.

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Nội dung Text: Novel triazine-based colorimetric and fluorescent sensor for highly selective detection of Al3+

Journal of Science: Advanced Materials and Devices 4 (2019) 237e244 Contents lists available at ScienceDirect Journal of Science: Advanced Materials and Devices journal homepage: www.elsevier.com/locate/jsamd Original Article Novel triazine-based colorimetric and ﬂuorescent sensor for highly selective detection of Al3þ J. Jone Celestina a, L. Alphonse a, P. Tharmaraj a, *, C.D. Sheela b a PG and Research Department of Chemistry, Thiagarajar College, Madurai 625009, Tamilnadu, India b PG and Research Department of Chemistry, The American College, Madurai 625002, Tamilnadu, India a r t i c l e i n f o a b s t r a c t Article history: This paper deals with a new ﬂuorescent assay of Al3þ ions with (2,20 -(6-((4-nitrophenyl)amino)-1,3,5- Received 31 January 2019 triazine-2,4-diyl) bis(hydrazine-2-yl-1-ylidene)) bis(indolin-3-one) (NADO) containing triazine moiety Received in revised form developed over other commonly coexisting metal ions. The complexation activity of NADO with various 26 April 2019 metal ions in an ethanolic solution is speciﬁcally studied by means of ﬂuorescent spectra. The NADO Accepted 8 May 2019 Available online 16 May 2019 exhibits a signiﬁcant ﬂuorescence enhancement at 469 nm in presence of Al3þ due to the formation of a complex. Under an optimized condition the detection limit is found to be 0.09 mM. As the concentration of Al3þ is increased, the ﬂuorescence intensity gradually increases due to the formation of the complex. Keywords: Fluorescent sensor The 1:1 binding stoichiometry between Al3þ and NADO is conﬁrmed by the Job's plot and the HR-LCMS Colorimetric mass spectrum of the metal complex. Aluminium ion © 2019 Publishing services by Elsevier B.V. on behalf of Vietnam National University, Hanoi. This is an Triazine open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/). Schiff base 1. Introduction selectivity and the capacity for rapid, real-time monitoring compared to other methods [3,4]. Schiff base acts as a good op- Aluminum being the third most abundant element has its tical and ﬂuorescent sensor due to its photophysical properties. widespread use in light alloy, textiles and in treatment of water. Triazine Schiff base, formed with active carbonyls and amines, Al3þ remains in blood and tissues for a very long time before it is will enhance the property of ﬂuorescence on complexation. It has excreted in the urine. World Health Organization holds the view been considered in various ﬁelds of chemistry due to its speciﬁc that the average daily human intake of aluminum is about 3e10 mg. properties like co-ordination ability which makes them appli- Human body tolerates an uptake up to 7 mg/kg of the body weight cable as a ﬂuorescent sensor in catalysts and in biological ﬁelds. per week. Aluminum in excess would lead to environmental In view of these facts, we designed the receptor as the target contamination and could be toxic to human health since it impedes sensor that could strongly bind the metal ions through Schiff base calcium metabolism, thereby causing Osteomalacia, inﬂuences the moiety [5,6]. In the present study, a functionalized triazine de- ingestion of iron in blood and also decreases the liver and kidney rivative, as a ﬂuorescent Al3þ sensor, is developed with a lowest functions. Excess accumulation of Al3þ leads to impairment of the detection limit of 0.09 mM. Our results exhibit an enhanced central nervous system, which is associated with the pathology of ﬂuorescence emission in ethanolic solution upon the addition of dementia, anemia, Parkinson's disease, Alzheimer's disease and Al3þ ions [6]. dialysis [1,2]. It is, therefore, desirable to detect and sense Al3þ ions and to 2. Experimental control their impact in biosphere. In previous reports, Zheng- qiang Li and co-workers have reported several detection methods 2.1. Materials for Al3þ ions among which ﬂuorescence detection offers several advantages such as high sensitivity, a facile analysis, an intrinsic All the needed chemicals were purchased from sigma Aldrich India and were used without further puriﬁcation. The metal chlo- * Corresponding author. ride salts were purchased from Merck chemicals. Ethanol was E-mail address: rajtc1962@gmail.com (P. Tharmaraj). purchased commercially and was further puriﬁed by a distillation Peer review under responsibility of Vietnam National University, Hanoi. method. Melting point of the synthesized ligand and its metal https://doi.org/10.1016/j.jsamd.2019.05.001 2468-2179/© 2019 Publishing services by Elsevier B.V. on behalf of Vietnam National University, Hanoi. This is an open access article under the CC BY license (http:// creativecommons.org/licenses/by/4.0/).
238 J.J. Celestina et al. / Journal of Science: Advanced Materials and Devices 4 (2019) 237e244 complex were analyzed by an electrical heating method at using 6-dihydrazinyl-N-(4-nitrophenyl)-1,3,5-triazine-2 amine. To the capillary tubes. dried precipitate (0.20 g, 1 mmol), Isatin (b) (0.24 g, 2 mmol) in ethanol was gradually added at 80 C and reﬂuxed for 24 h. As a 2.2. Characterization completion of the reaction, a dark yellow precipitate NADO (c) starts separating out. It is shown in Fig.S1. The precipitate obtained The 1H NMR and 13C NMR was recorded using a 400 MHz Bruker was collected by ﬁltration and washed several times with ethanol NMR instrument. A FT-IR spectrometer in the range and dried in vacuum. It was puriﬁed by column chromatography 4000e400 cm1 was used to record the spectra using a KBr pellet. using neutral alumina in a mixture of (Ethyl acetate/Hexane). The LCMS and HR-LCMS mass spectra were recorded in the Bruker mass spectrometer using acetonitrile as the solvent. Absorption 2.4. Synthesis of Al3þ-NADO complex and emission properties of NADO with different metal ions were recorded in UV-Visible Jasco (V-530) and FP-6200 Spectropho- The complex was prepared using an ethanolic solution of AlCl3 tometer instruments. (0.15 g, 1 mmol) and an ethanolic solution of NADO (0.32 g, 1 mmol) in 1:1 (ligand:metal) molar ratio by reﬂuxing for two hours as 2.3. Synthesis of NADO shown in Fig.S2. The obtained precipitate was washed with abso- lute ethanol and dried. The triazine Schiff base ligand was prepared using ethanol. 4- nitroaniline (0.50 g, 2 mmol) in acetone, was stirred with cyanu- 2.5. Job's plot measurements ric chloride under ice cold condition for about 4 h and the yellow solid obtained was ﬁltered and dried. The precipitate obtained was NADO (1 mg) and 0.1 mg of AlCl3 are dissolved in ethanol. The allowed to stir for an hour with hydrazine hydrate to get (a) 4, solution mixture is taken and poured into the glass vials. Different Table 1 Physical and analytical data of NADO and [Al(NADO)Cl]Cl2 complex. Compound M.W. g/mol1 Colour Calculated (Found) (%) M.p. ( C) C H O N M C25H17N11O4 (NADO) 535.47 Yellow 56.08 (56.05) 3.20 (3.18) 11.95 (11.88) 28.77 (28.79) e 195e198 C [Al(NADO)Cl]Cl2 667.10 Dark Yellow 50.14 (50.16) 3.03 (3.04) 25.73 (25.70) 22.01 (21.98) (4.51) 254e256 C 4.53 Fig. 1. (a) UVevis spectrum of ligand (NADO), (b) UVevis spectra of NADO (20 mM) after addition of metal cations and anions (c) UVevis spectra of NADO after adding (0.10e0.90) mM of Al3þ ion.
J.J. Celestina et al. / Journal of Science: Advanced Materials and Devices 4 (2019) 237e244 239 concentrations (0.1e1.0 mM) of AlCl3 are added to the vials con- taining the NADO and shaked for getting clear solutions. After shaking the solution is transferred into the UV-visible cuvette and the UVevis absorption spectrum is taken using UV-visible spec- trophotometer between the ranges 200 nme800 nm at room temperature. 2.6. Elemental analysis and conductivity measurements The synthesized NADO and [Al(NADO)Cl]Cl2 complex was ob- tained in good yield with high purity. The data of the complex conﬁrms the formation of 1:1 (M:L) coordination Al3þ with NADO as shown in Table 1. The percentage of C,H,N was measured in a Vario EL- III CHNS Analyzer. Melting points of the synthesized NADO and its [Al(NADO)Cl]Cl2 complexes were analyzed in the buchi melting point analyzer. The electrolytic conductance of the synthesized complex was studied with the help of the con- ductometer with ethanol as the solvent. Initially the cell constant value is 1. Fig. 3. FT-IR Spectrum of NADO. 3. Results and discussion 3.1. Absorption studies of NADO The sensing property of NADO with different metal cations was investigated by preparing stock solutions of NADO (1 103 mM) and metal cations in anhydrous ethanol [7] and its coordination properties with various metal cations were measured by the UVeVis Spectrometer. The free NADO showed maximum ab- sorption bands at 268 nm (37,313 cm1) and 326 nm (30,675 cm1) which are due to the p / p* transition [8] as shown in Fig. 1(a). When the metal ions were added to the NADO, there was no speciﬁc change observed with the metal cations and an- ions like (Zn2þ, Ni2þ, Fe2þ, Fe3þ, Cu2þ, Al3þ, Co2þ, Mg2þ, Ca2þ, Bi2þ, Hg2þ, As2þ, Cr3þ, CO2 2 3 3 3 , SO4 , PO4 , NO , NO 2 and Cr2O2 7 ) except for Al3þ which gave a new band with increasing intensity Table 2 UV-Vis spectral data of NADO and [Al(NADO)Cl]Cl2 complex. Compounds Frequency Transition Geometry Electrolytic cm1 conductance S/m Fig. 4. FT-IR Spectrum of the complex [Al(NADO)Cl]Cl2. NADO 30,675 p / p* e e 37,313 at 515 nm (19,417 cm1) corresponding to the 3A2g(F) / 3T1g(P) transition and at 657 nm (15,220 cm1) corresponding to the 3 3 [Al(NADO)Cl]Cl2 19,417 A2g(F)/ T1g(P) distorted 173 4 15,220 T1g(F)/4A2g(F) octahedral 4 T1g(F) / 4A2g(F) region as clearly shown in Fig. 1(b) [9e11]. The Fig. 2. (a) Emission spectra of NADO with different metal ions and (b) Emission intensity at 469 nm as a function of Al3þ at different concentrations (0.10e0.80 mM).
240 J.J. Celestina et al. / Journal of Science: Advanced Materials and Devices 4 (2019) 237e244 Table 3 Infrared spectral data of the compound NADO and the [Al(NADO)Cl]Cl2 complex. Compound n C¼N cm1 n C¼N cm1 triazine ring n N-H cm1 n Al-N cm1 n Al-O cm1 n C-N cm1 Ligand (NADO) 1626 1401 3139 e e 1324 [Al(NADO)Cl]Cl2 1590 1398 3129 568 749 1327 latter transition might be due to the formation of a distorted interference in selectively detecting Al3þ. In Fig. 1(c) with octahedral complex of Al3þ with NADO [1] as presented in Table 2. increasing equivalents of Al3þ added to the solution of NADO, the Though Zn2þ gave a small shift in the absorbance it is considered concentration of Al3þ increases with the consecutive decrease in negligible and it is not because of the complex formation [12]. the concentration of NADO which conﬁrms the presence of the The interference experiments clearly show that Zn2þ has no Al3þ complex in equilibrium with the free NADO. A well-deﬁned isosbestic point at 401 nm clearly conﬁrms the complex forma- tion of Al3þ with the NADO resulting in a red shift [13,18,34]. 3.2. Fluorescent studies of NADO The selective ability of NADO towards Al3þ in ﬂuorescence in the presence of various metal ions was investigated in ethanol, as shown in Fig. 2(a). Free NADO showed weak ﬂuorescence emission bands due to ﬂuorescent quenching by lone pair of electrons from oxygen and nitrogen atoms, which results in the photo-induced electron transfer (PET) [14]. When Al3þ ions were added, the ﬂuorescence intensity of the ligand at 469 nm was enhanced without any spectral changes which indicates a high selectivity of NADO for Al3þ ions by means of chelation [11,15] Upon addition of (Zn2þ, Ni2þ, Fe2þ, Fe3þ, Cu2þ, Al3þ, Co2þ, Mg2þ, Ca2þ, Bi2þ, Hg2þ, As2þ, Cr3þ, CO2 2 3 3 3 , SO4 , PO4 , NO , NO 2 and Cr2O27 ) ions into NADO, no obvious ﬂuorescence response could be observed except for Zn2þ and Fe2þ which ions slightly increased the emission in- tensity with little interference in detecting Al3þ. The Fluorescence response of the NADO to various concentrations of Al3þ (0.10e0.80 mM) showed a gradual increase in intensity [12,34] as Fig. 5. Jobs Plot for determining the stoichiometry of NADO and Al3þ in ethanol. shown in Fig. 2(b). At 0.80 mM the maximum precipitation occurs. Fig. 6. Proposed sensing mechanism of Al3þ ion by NADO.
J.J. Celestina et al. / Journal of Science: Advanced Materials and Devices 4 (2019) 237e244 241 Fig. 7. HOMO and LUMO energy levels of NADO and [Al(NADO)Cl]Cl2. The interference studies clearly show the selective sensing ability of present in NADO [19,20]. The sharp intense band in the region of Al3þ ion compared with that of other cations with the highest 1324 cm1 in the ligand is attributed to the carbonyl C-N stretching ﬂuorescence intensity at 469 nm. It underlines the excellent spec- vibration and it was shifted to higher frequency 1327 cm1 for the iﬁcity to Al3þ. Al3þ complex. The band at 1401 cm1 is characteristic of triazine moiety which is shifted to 1398 cm1. The sharp peak at 749 cm1 3.3. FT-IR spectral studies strongly supports the bond formation nAl-O of metal through carbonyl oxygen of the Schiff base ligand to the Al3þ ion [20,21]. In Fig. 3, the NADO has a broad absorption band in the region of The metal complex formation was further conﬁrmed by the 3139 cm1 due to the e NH stretching vibration [12]. This band is appearance of sharp peaks at 568 cm1 nAl-N in the spectrum of slightly shifted by the formation of the Al3þ complex and a new the metal complex in Fig. 4 which is assignable to stretching vi- band appears at 3129 cm1 [16e18] which indicates the formation brations [22]. The coordination through azomethine nitrogen was of a metal complex with nitrogen present in the NH group that is supported by the shifting of nC ¼ N towards higher frequencies
242 J.J. Celestina et al. / Journal of Science: Advanced Materials and Devices 4 (2019) 237e244 is attributed to the [NADO] [Al (NADO)Cl]Cl2 complex (calculated: 667.01) [36e39] and is shown in Fig. S7. The mass data, therefore, conﬁrm the binding of Al3þ to ligand with 1:1 stoichiometry [16]. The conductivity measurement value of 173 S/m corresponds to the proposed structure with two chlorine ions present outside the coordination sphere in the metal complex (Fig. 6). 3.5. Theoretical studies In order to support the results obtained from the 1H- NMR and HR-LCMS mass spectral analysis, an optimization of the structures of both NADO and [Al (NADO)Cl]Cl2 were performed at the hybrid basic sets B3LYP/6-3 g(d) level in the Gaussian program. The ob- tained result is in accordance with the results of the NMR and Mass spectral data [40]. The optimized results exposed an octahedral structure. It is found that [Al (NADO)Cl]Cl2 is better stabilized than NADO. The energy gap of HOMO and LUMO of NADO and the Al3þ complex is (DE ¼ 3.5919 eV and DE ¼ 2.4038 eV). The value of the Al3þ complex is found to be comparatively lower than that of Fig. 8. Effect of pH on [Al(NADO)Cl]Cl2 complex. NADO, indicating a bathochromic shift towards longer wavelength in the absorption spectrum. In the optimized structure of the Al3þ NADO complex HOMO as given in Fig. 7, electrons are mostly with respect to that observed at 1626 cm1 in the free ligand while occupied in the ligand rings whereas, on the other hand, LUMO the new shifted peak appears at 1590 cm1 in the metal complex electrons are occupied both by the ligand rings and the Al center. In given in Table 3 [11,16,23]. The absence of the carbonyl amide band view of these results, ICT (intramolecular charge transfer) is taking at 1660 cm1 in NADO is a strong evidence for amidoeimido place efﬁciently in the mechanism of forming the Al3þ complex [41] tautomerism which takes place before complexation. It is also (Fig. 8). correlated by the decrease in the NH bending vibrations of the Al3þ metal complex with NADO and by the presence of a new peak at 3.6. Stoichiometry and binding mechanism of NADO with Al3þ 1589 cm1 in the spectrum of the Al3þ NADO complex [24]. In the metal complex, the bands shifts to lower frequency indicate that The binding mechanism of NADO e Al3þ was studied by ﬂuo- the tautomerism is inhibited in the Al3þ complex and that the rescence spectral changes, by mass spectrometry [42] and by 1H imine nitrogen and carbonyl oxygen are involved in the coordi- NMR and FT-IR spectral studies [38]. Free NADO, which has poor nation to the metal [25]. ﬂuorescence, is enhanced by the isomerization of C¼N (azomethine carbon and hydrogen) double bond in the excited state [36] by Al3þ 3.4. NMR and mass spectral studies metal on stable chelation. Increase in ﬂuorescence takes place and the Photo Induced Electron Transfer (PET) is inhibited (when the To understand the binding mode of NADO with Al3þ, a 1H NMR metal gets binded to NADO, the PET is stopped). In Fig. 2, NADO, as spectrum analysis is done in DMSO-d6. The ﬁne spectra of the such being low in ﬂuorescence because of intramolecular photo- NADO and Al3þ metal complex are shown in Fig.S3 and Fig.S4. The induced electron transfer, on rapid addition of Al3þ shows 1 H NMR spectrum of NADO shows the characteristic imine peak at enhanced ﬂuorescence. Thus the enhancement in ﬂuorescence ul- 8.11 ppm and the aromatic protons are centered from 6.96 ppm to timately leads to the complex formation [11]. The detection limit 7.87 ppm. The 1H NMR spectrum of the Al3þ complex shows the (DL) of NADO to Al3þ was found to be lowest with the value of merging of two singlet peaks at 6.98 ppm, a doublet at 7.6 ppm 0.09 mM compared with the recent literatures as given in Table 4. and they are downshifted [26]. A peak at 8.2 ppm undergoes a The binding stoichiometry of ligand NADO to Al3þ was calculated downshift as well. Complexation of NADO with Al3þ was by the Job's method on the basis of ﬂuorescence emission spec- conﬁrmed by the shifted proton peaks towards lower magnetic trum. In Fig. 5 the ﬂuorescence intensity at 469 nm exhibited a ﬁelds due to the reduction of the electron density upon coordi- maximum mole fraction at 0.50 demonstrating a possible 1:1 nation to the metal ion [27e31]. 13C NMR spectrum of NADO as binding stoichiometry between Al3þ and NADO. given in Fig.S5 also conﬁrms the formation of NADO. The Mass spectrum of the NADO and Al3þ are examined by LCMS and HR- 3.7. Effect of pH on ﬂuorescence in presence of Al3þ with NADO LCMS mass spectrum analysis using acetonitrile as the solvent [32,33]. Fig. S6 clearly conﬁrms the formation of the NADO with To observe the binding interaction of NADO with Al3þ at the observed m/z peak at 536.53 (M þ H)þ [34,35]. The observed different pH's, both acidic and basic pH solutions were used. The m/z peak for NADO in the presence of Al3þ at 666.06 (M-H)- peak interaction between NADO and the Al3þ ion was investigated at a Table 4 Detailed comparison of lod of various Al3þ sensors by ﬂuorescence responses. Probe Selectivity Method Solvent LR Lod (mM) Ref Naphthol- Quinoline Fluorescent chemosensor Al3þ Fluorescence DMF 0-16 equivalence 1.0 mM [15] Fluorescent chemosensor Al3þ Fluorescence DMSO 0.1e0.5 mM 0.1 mM [12] Amphiphilic Carbon dots Al3þ Fluorescence Ethanol 8e20 mM 1.1 mM [30] Fluorescent chemosensor Al3þ Fluorescence CH3OH/Water 0.5e10 mM 0.43 mM [36] Triazine schiff base Al3þ Fluorescence Ethanol 0.1e0.8 mM 0.09 mM Present work
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