Startseite Synthesis of a benzothiazole-based structure as a selective colorimetric-fluorogenic cyanate chemosensor
Artikel Open Access

Synthesis of a benzothiazole-based structure as a selective colorimetric-fluorogenic cyanate chemosensor

  • Emine Kayhan EMAIL logo , Selahattin Bozkurt und Mehmet Kayhan
Veröffentlicht/Copyright: 31. Dezember 2023
Artikel downloaden (PDF)
Veröffentlichen auch Sie bei De Gruyter Brill
Manuskript einreichen Informationen für Autor*innen
Reviews in Analytical Chemistry
Aus der Zeitschrift Reviews in Analytical Chemistry Band 42 Heft 1

Abstract

In this study, a new heterocyclic compound incorporating a benzothiazole moiety was specifically designed for the detection of cyanate anions, employing a hydrogen bonding mechanism. Through strategic integration of triazine and phenylenediamine cyclic groups into the compound’s structure, intramolecular hydrogen bonding interactions between the donor and acceptor sites were enhanced, leading to exceptional sensitivity towards cyanate anions. Utilizing the amino-type excited-state intramolecular proton transfer phenomenon, this new compound exhibited dual signals and achieved a significant Stokes’ shift via proton transfer, coupled with aggregation-induced emission properties. This unique combination resulted in visible color changes and an impressive fluorescence response, offering a promising solution for the sensitive detection of cyanate ions in critical environmental matrices. Cyanate detection at low concentrations by this as-synthesized compound (L1), accompanied by a distinct color change and a gradual fluorescence increase upon incremental cyanate addition demonstrated L1’s selectivity, as confirmed in the presence of various competing anions F−, Cl−, Br−, I−, ClO 3 − , ClO 4 − , NO 3 − , BrO 3 − , CN− and CNO−. Spectrofluorometric investigations demonstrated that L1 shows significant potential as a selective cyanate anion detection candidate.

Keywords: ESIPT; aggregation-induced emission; cyanate detection; sensor; benzothiazole

1 Introduction

Industries annually produce approximately 5 million metric tonnes of hazardous waste, predominantly consisting of anions, heavy metals, pesticides, and complex aromatic compounds [1]. Among anions, the cyanide anion (CN−) stands out as it neither accumulates in the body nor leads to chronic illnesses. However, due to its capability to form complexes by binding with iron in the blood, it can obstruct the transfer of oxygen to cells, resulting in suffocation for both humans and animals. Likewise, cyanide anion leads to the inhibition of cytochrome oxidase and is toxic to freshwater fish, primarily by obstructing electron transport and impeding energy release within cells [2]. Consequently, owing to the harmful effects of the cyanide anion on the environment, including air, water, and soil, as well as its direct impact on human health, stringent regulations have been implemented worldwide [1].

Thus, cyanide anion-containing waste is converted into less toxic cyanate (CNO−) to reduce the hazardous properties of cyanide compounds. Therefore, several traditional techniques, such as chromatography [3] spectrophotometry [4,5], voltammetry [6,7], and electrochemical [8] and titrimetric [9,10] methods, have been widely used to check if the ion concentrations of both cyanide and cyanate are under the acceptable limits. These techniques suffered from various limitations, including low detection limits, complex procedures, costly equipment, and time-consuming analysis.

Compared to traditional analytical methods, fluorescence spectroscopy as a non-destructive method offers distinct advantages such as exceptional sensitivity, high selectivity, and rapid analysis yielding quick and real-time results, thus facilitating efficient monitoring of cyanate and cyanide levels in the ecosystem [11]. As a result, there is a significant need for the advancement of a fast, precise, and sensitive method to detect CN− and CNO− ions at µg·L−1 levels in crucial life matrices. The emergence of fluorescent chemosensors, which exhibit remarkable selectivity and sensitivity towards toxic analytes, has garnered substantial interest within the sensors domain [12].

When anion-specific fluorescent chemosensors come into contact with a particular anion, they undergo a chemical reaction or binding event that leads to a change in their fluorescence properties. This change can be observed as a shift in the emitted light’s wavelength, intensity, or color through signaling mechanisms like chelation-enhanced fluorescence, excited-state intramolecular proton transfer (ESIPT), and aggregation-induced emission (AIE). The detection methods of cyanide ion-specific fluorescent chemosensors primarily rely on the receptor–reporter interactions, encompassing electron-deficient site mechanism, nanotechnical approach, and coordination-based or hydrogen-bonding detection [13,14,15,16,17]. In this context, heterocyclic compounds derived from well-known structures like crown ethers, cyclodextrins, cucurbiturils, and pillararenes, and benzothiazole derivatives are frequently utilized as fluorescent receptors for detecting anions [18,19,20,21,22]. Among them, modifying benzothiazole derivatives with electron-donating/-withdrawing groups shows amino-type ESIPT characteristics with resolvable two fluorescence emission bands due to ground state (enol) to excited state (keto) tautomerism [22,23].

Herein, we introduced AIE and amino type-ESIPT active new heterocyclic compound with benzothiazole moiety for colorimetric and fluorometric detection of cyanate anions through a hydrogen bonding mechanism. In this study, aminophenyl benzothiazole was functionalized with triazine and phenylenediamine, including cyclic groups in order to enhance the intramolecular hydrogen bonding between donor and acceptor sites. By combining the amino-type ESIPT phenomenon giving the dual signal and enabling a significant Stokes’ shift by proton transfer and with AIE features, a new heterocyclic compound exhibited exceptional selective sensitivity to the cyanate anion, resulting in visible color alterations and an impressive fluorescence reaction.

2 Materials and methods

2.1 General procedures

All the solvents and chemical reagents used in the study were of high purity, specifically spectroscopic/reagent grade, and were sourced from Merck/Sigma Aldrich without further purification. Flash column chromatography was employed for purification, utilizing silica gel Merck 60 with mesh sizes in the range of 230–400 (0.040–0.063 mm). Thin layer chromatographic (TLC) analyses were conducted using silica gel (Merck TLC silica gel 60G, F 254) aluminum plates as a means of monitoring reactions. Melting points were determined using a Gallenkamp Electrothermal melting point apparatus with no corrections applied. All spectroscopic measurements were conducted at room temperature.

FT-IR spectra were acquired using a PerkinElmer Spectrum Two FT-IR Spectroscopy equipped with an ATR apparatus. UV-Vis spectra were recorded with a PerkinElmer Lambda 35 Spectrophotometer, using quartz cuvettes with a 1 cm path length. Fluorescence spectral studies were carried out using an Agilent Cary Eclipse Fluorescence Spectrophotometer, with emission spectra corrected using the spectrometer’s software and quartz cuvettes with a 1 cm path length.

For NMR analysis, both 1H and 13C spectra were obtained using a Bruker 400 MHz spectrometer in deuterated chloroform (CDCl3) and dimethyl sulfoxide (DMSO-d 6) as solvents, and chemical shifts (δ) were reported in ppm units relative to tetramethylsilane. High-resolution mass spectrometry was performed on an Agilent 6230 TOF-MS instrument using the electrospray ionization technique in positive ion mode.

2.2 Synthesis of the L1 compound

Compound 2 was synthesized following the procedure outlined in a prior publication[24]. N 2 ,N 4-Bis(2-aminophenyl)-N 6-(2-(benzo[d]thiazol-2-yl)phenyl)-1,3,5-triazine-2,4,6-triamine (referred to as L1) was prepared as follows: A solution containing 0.2 mmol of Compound 2 and 1.2 equiv. of diisopropylethylamine (DIPEA) in 20 mL of tetrahydrofuran (THF) was combined with a mixture of 0.92 mmol 1,2-diaminobenzene in the same 20 mL of organic solvent. This addition was performed drop by drop at 0°C, followed by refluxing for 3 h. Upon completion of the reaction, the solvent was evaporated under reduced pressure, and the resulting crude product was subjected to flash chromatography on silica gel (using a Hexane:EtOAc (10:1) solvent system) to yield L1 in the form of a brown solid. The yield achieved was 46%, and the melting point was greater than 300°C.

2.3 Preparation of anion solutions

To create solutions containing anions, we started by preparing stock solutions with various analytes like fluoride (F−), chloride (Cl−), bromide (Br−), iodide (I−), chlorate ( ClO 3 − ), nitrate ( NO 3 − ), and cyanide (CN−) by diluting the corresponding inorganic salts (tetrabutylammonium, sodium, or potassium) to a concentration of 1.5 × 10−3 M using deionized water. These stock solutions were then further diluted as necessary with the appropriate solvent system to achieve the desired concentrations.

For the preparation of the CNO− anion solution following the standard method 4500-CN, three separate solutions were required: chloramine T, phosphate buffer, and cyanide. First, we dissolved 84 mg of chloramine T in 100 mL of water to create the chloramine T solution. Next, for the phosphate buffer solution, we dissolved 1.38 g of NaH2PO4·H2O in 100 mL of water. Finally, for the cyanide solution, we dissolved 0.251 g of KCN and 0.2 g of KOH in 100 mL of water. Afterward, we pipetted 3.9 mL of the cyanide (third solution) and diluted it to 100 mL with 0.04 M NaOH, resulting in a 1.5 × 10−3 M cyanide solution. To this solution, we immediately added 0.1 mL of chloramine T and 0.1 mL of phosphate buffer to achieve the desired concentration of CNO−. This process allowed us to obtain CN− in the form of its oxidizing product, CNO−, in an alkaline medium in the presence of chloramine T.

3 Results and discussion

3.1 Photochemical properties of the new benzothiazole-triazine derivative compound (L1)

Detecting various anions commonly used in industry within aquatic environments holds significant importance for both environmental preservation and human well-being. Therefore, this research focused on investigating the creation of compounds featuring functional groups capable of engaging in diverse interactions, such as hydrogen bonding, within their molecular structure when exposed to different anions. To initiate this inquiry, we commenced by synthesizing a thiazole-based triazine skeleton referred to as L1.

In the synthesis process outlined in Scheme 1, cyanuric chloride was made to react with 2-(2-aminophenyl)benzothiazole 1 in THF in the presence of DIPEA. Subsequently, compound 2 was generated through the reaction of compound 1 with 1,2-diaminobenzene, with a 46% yield.

Scheme 1 Synthetic pathway of our sensor candidate as compound L1; i: cyanuric chloride, DIPEA, THF, 0°C; ii: 1,2-diaminobenzene, DIPEA, THF, reflux.
Scheme 1

Synthetic pathway of our sensor candidate as compound L1; i: cyanuric chloride, DIPEA, THF, 0°C; ii: 1,2-diaminobenzene, DIPEA, THF, reflux.

The structural characteristics of the newly synthesized fluorescent compound, L1, were identified using a combination of analytical techniques including FTIR and 1H and 13C NMR. Examination of the FT-IR spectrum revealed the presence of the C═N band of benzothiazole at 1,609 cm−1. The 1H NMR data exhibited NH protons in the chemical shift range of 11.88–11.52 (multiplet) and 9.63–9.40 (multiplet) ppm for compound L1. Apart from these, in the 1H NMR spectrum, various aromatic groups present in the structure were observed between 8.55 and 6.91 ppm.

Characterization data for L1 are as follows. FTIR (ATR) cm–1: 1,609 (C═N); 1H NMR (400 MHz, DMSO‐d 6) δ 11.88–11.52 (m, 1H, NH), 9.63–9.40 (m, 2H, NH), 8.55–8.44 (m, 1H, ArH), 8.24 (d, J = 8.0 Hz, 1H, ArH), 8.16–7.96 (m, 2H, ArH), 7.71–7.62 (m, 1H, ArH), 7.59–7.51 (m, 1H, ArH), 7.45–7.20 (m, 3H, ArH), 7.15–6.97 (m, 1H, ArH), 6.89–6.79 (m, 1H, ArH), 6.72–6.62 (m, 1H, ArH), 6.91 (dd, J = 5.7, 3.5 Hz, 2H, ArH), 6.91 (dd, J = 5.7, 3.4 Hz, 2H, ArH), 4.94 (bs, 4H, NH 2); 13C NMR (100 MHz, DMSO‐d 6) δ 163.09, 161.97, 161.88, 161.40, 152.49, 140.78, 138.54, 132.99, 132.12, 130.21, 129.87, 126.74, 125.58, 125.51, 125.26, 125.06, 122.74, 122.38, 122.01, 120.69, 120.47, 117.19; Anal. Calcd for C28H23N9S (727.27): C, 64.96%; H, 4.48%; N, 24.35%; S, 6.19%; found: C, 64.97%; H, 4.48%; N, 24.35%, and S, 6.19%.

Although L1 demonstrated solubility in THF or dimethyl sulfoxide (DMSO), it exhibited insolubility in water or hexane. Notably, when L1 was dissolved in these solvents, it remained non-emissive. However, as the water content was gradually increased step by step (% fraction of water), fluorescence emissions were observed, along with the appearance of turbidity, as depicted in Figure 1. This phenomenon can be attributed to the increased hydrogen-bonding capacity of solvents like water or the presence of guest molecules, such as ions, which led to an increase in emission values. This increase can be attributed to the restricted rotation of benzothiazole derivatives in response to these factors [25,26,27].

Figure 1 Photographs of compound L1 in DMSO–H2O mixtures with different water fractions (10–95%) under 365 nm UV light.
Figure 1

Photographs of compound L1 in DMSO–H2O mixtures with different water fractions (10–95%) under 365 nm UV light.

From this perspective, it was observed that the emission of the L1 molecule increased upon complexation with anions, as explained previously. Additional evidence supporting the AIE effect comes from the evaluation of the fluorescence quantum yield (Φf) of L1 in solvent mixtures of DMSO and H2O, using quinine sulfate as a reference material. The Φf values remained consistent for solvent mixtures containing less than 60 vol% H2O. However, as the H2O content in the solvent mixtures increased further, the corresponding Φf values exhibited a rapid increase. Consequently, in line with similar findings in the existing literature, compounds possessing the aforementioned characteristics are indicative of AIE properties [28,29,30,31,32].

To comprehensively assess the photophysical properties of our chemosensor candidate L1, fluorescence tests were conducted in different fractions of DMSO:H2O (10–95%). Interestingly, upon excitation of L1 at 350 nm, two emission bands at 497 and 567 nm were exhibited, respectively, in the DMSO:H2O mixture (10–60%) at a concentration of 1.88 × 10−5 M. The existence of dual bands and large Stokes’ shift of 217 nm supported the remarkable ESIPT nature of L1. These two peaks were identified as enolic (497 nm; lower wavelength) and keto forms (567 nm; higher wavelength), respectively [33,34]. As water formed strong hydrogen bonding between amino groups of L1, the molecule was transformed from the ground state (enol form) to the excited state (keto form).

However, when the water amount was incrementally increased (>60%), the ESIPT phenomenon was inhibited, as the lower wavelength emission band disappeared and the higher wavelength band was blue-shifted [35]. A gradual increase in the fluorescence emission band intensity was observed till 80% H2O (as shown in Figure 2b). These findings are in line with color alterations in Figure 1, suggesting the AIE-active nature of L1 in higher fractions of H2O due to agglomeration of complexes.

Figure 2 (a) Normalized absorption and fluorescence spectra of L1 in 10% water. (b) Emission spectra of L1 in DMSO:H2O mixtures.
Figure 2

(a) Normalized absorption and fluorescence spectra of L1 in 10% water. (b) Emission spectra of L1 in DMSO:H2O mixtures.

3.2 Fluorescence response of compound L1 toward various anions

Motivated by the anion-detecting capabilities of benzothiazole derivatives, we embarked on an exploration to observe the visible response of L1 towards a range of anions under 365 nm UV light. Out of the array of ions examined, including fluoride (F−), chloride (Cl−), bromide (Br−), iodide (I−), chlorate ( ClO 3 − ), perchlorate ( ClO 4 − ), nitrate ( NO 3 − ), bromate ( BrO 3 − ), and cyanide (CN−), only the introduction of cyanide into the probe solution produced a distinct color change (as shown in Figure 3a). Specifically, the color transformation occurred instantly, shifting from colorless to cyan by using the so-called standard method (SM) 4500-CN [36], in which an aqueous cyanide solution was added to a mixture of chloramine T and phosphate buffer. The solution of L1 and cyanate showed green emission with emission maxima at 497 nm having a large Stokes’ shift of 147 nm (Figure 3b).

Figure 3 (a) Photograph of L1 (1.88 × 10−5 M) with different anions (10 equiv) in aqueous DMSO solution under 365 nm UV light. (b) Fluorescence emission spectra when L1 (at a concentration of 1.88 × 10−5 M) was subjected to different anions (10 equiv).
Figure 3

(a) Photograph of L1 (1.88 × 10−5 M) with different anions (10 equiv) in aqueous DMSO solution under 365 nm UV light. (b) Fluorescence emission spectra when L1 (at a concentration of 1.88 × 10−5 M) was subjected to different anions (10 equiv).

To assess the potential interference of other anions when detecting the cyanate anion, L1 was exposed to cyanate in the presence of additional anions, including F−, Cl−, Br−, I−, ClO 3 − , ClO 4 − , NO 3 − , and BrO 3 − . The test for interference from these anions confirmed that they did not adversely affect the selectivity of L1 towards cyanate (as depicted in Figure 4). Consequently, L1 enables the fluorometric detection of cyanate, which is less toxic than cyanide. This provides a valuable technique for cyanide detection in scenarios where direct detection by L1 is not feasible, such as in the presence of chloramine T and phosphate buffer.

Figure 4 Fluorescence spectra of L1 (1.88 × 10−5 M in DMSO:H2O; 60:40) solution with other anions in the presence of cyanate anions.
Figure 4

Fluorescence spectra of L1 (1.88 × 10−5 M in DMSO:H2O; 60:40) solution with other anions in the presence of cyanate anions.

In order to examine the cyanate detection efficiency of L1, an aqueous solution of cyanate was added to the solution of L1 in incremental steps, ranging from 1 to 20 equiv. As can be seen in Figure 5a, visible color changes into cyan were observed upon the addition of 7 equiv of cyanate solution under 365 nm UV light. Moreover, the cyan color gets brighter as the concentration of cyanate increases from 7 equiv to 20 equiv, which is in agreement with the AIE property, so the colorimetric behavior of L1. Besides that, the fluorescence response of L1 towards the cyanate concentration (1–20 equiv) was also studied. L1 gave a broad emission band centered at 597 nm upon the introduction of cyanate. The stepwise addition of cyanate from 1 to 20 equiv led to an intensity decrease of the band at 567 nm whereas an intensity increase of the band at 497 nm was observed (as shown in Figure 5b). This can be explained by the hydrogen bonding of L1 with water in the solution dominated by a small amount of cyanate addition. Upon further increasing the amount of cyanate, hydrogen bonding between cyanate and the L1 compound prevailed due to the amino-type ESIPT behavior of the L1 compound.

Figure 5 (a) Photograph of L1 (1.88 × 10−5 M) exposed to varying concentrations of cyanate (1–20 eq.) in DMSO:H2O (60:40) solution under 365 nm UV light. (b) Fluorescence spectral changes of L1 toward variable equivalents of cyanate in DMSO–H2O solution.
Figure 5

(a) Photograph of L1 (1.88 × 10−5 M) exposed to varying concentrations of cyanate (1–20 eq.) in DMSO:H2O (60:40) solution under 365 nm UV light. (b) Fluorescence spectral changes of L1 toward variable equivalents of cyanate in DMSO–H2O solution.

The practical applicability of L1 was further evaluated with CNO− detection experiments in real sample (tap water) analysis. The results in Table 1 showed an excellent agreement with those spiked CNO− with good recovery between the range of 95.7% and 97.2% and low relative standard deviation (RSD) below 0.89%, which proved the accurate, reliable, and feasible real sample application of L1 as a convenient fluorescent sensor for CNO− detection in environmental samples.

Table 1

Determination of CNO− anions in tap water samples (n = 3)

Entry Spike (µM) Founda µM ± SD Recovery (%) RSDb (%)
1 2.0 1.95 ± 0.02 97.5 0.84
2 2.5 2.43 ± 0.02 97.2 0.89
3 3.0 2.93 ± 0.02 97.7 0.56

aThe mean values of three duplicated tests. bThe relative standard deviations of three tests.

4 Conclusions

A new benzothiazole derivative heterocyclic compound (L1) with AIE and amino type-ESIPT characteristics was synthesized through a facile method to detect the hazardous cyanate.

A solution of L1 in DMSO gave visible color changes even upon the addition of water (>50%) due to the AIE-active nature of L1. Fluorescence studies supported the remarkable ESIPT property of L1 with dual bands and large Stokes’ shift of 217 nm due to the hydrogen bonding between L1 and water. Moreover, cyanate was detected even at low concentrations by L1 with a distinguishable color transformation. The fluorescence response of L1 gradually increased upon incremental addition of cyanate. Selectivity of L1 was proved in the presence of various competing anions of F−, Cl−, Br−, I−, ClO 3 − , ClO 4 − , NO 3 − , BrO 3 − , CN−, and CNO−.

Thus, spectrofluorometric studies revealed that L1 is a promising candidate for the detection of cyanate anion selectively.

  1. Funding information: Authors state no funding involved.

  2. Author contributions: Emine Kayhan: writing – original draft, writing – review & editing, conceptualization, methodology, and formal analysis; Selahattin Bozkurt: writing – original draft, formal analysis, visualization, and project administration; Mehmet Kayhan: writing – review & editing, data curation, and formal analysis.

  3. Conflict of interest: Authors state no conflict of interest.

  4. Data availability statement: The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.

References

[1] Rao MN, Sultana R, Kota SH. Hazardous waste. In: Rao MN, Sultana R, Kota SH, editors. Solid and hazardous waste management. Oxford, United Kingdom: Butterworth-Heinemann; 2017. p. 159–207.10.1016/B978-0-12-809734-2.00005-5Suche in Google Scholar

[2] Rohmah MK, Salahdin OD, Gupta R, Muzammil K, Qasim MT, Al-qaim ZH, et al. Modulatory role of dietary curcumin and resveratrol on growth performance, serum immunity responses, mucus enzymes activity, antioxidant capacity and serum and mucus biochemicals in the common carp, Cyprinus carpio exposed to abamectin. Fish Shellfish Immunology. 2022;129:221–30. 10.1016/j.fsi.2022.08.042.Suche in Google Scholar PubMed

[3] Destanoğlu O, Yılmaz GG. Determination of cyanide, thiocyanate, cyanate, hexavalent chromium, and metal cyanide complexes in various mixtures by ion chromatography with conductivity detection. J Liq Chromatogr Relat Technol. 2016;39(9):465–74. 10.1080/10826076.2016.1192044.Suche in Google Scholar

[4] Manivannan R, Ciattini S, Chelazzi L, Elango KP. Benzoquinone–imidazole hybrids as selective colorimetric sensors for cyanide in aqueous, solid and gas phases. RSC Adv. 2015;5:87341. 10.1039/C5RA13597D.Suche in Google Scholar

[5] Feng J, Zhong J, Tang X. Selective and sensitive detection of cyanate using 3-amino-2-naphthoic acid-based turn-on fluorescence probe. Anal Bioanal Chem. 2019;411:3613. 10.1007/s00216-019-01843-w.Suche in Google Scholar PubMed

[6] Gupta S, Chhibber M, Mittal SK. Amine derivative of triphenyl ether as an optical sensor for the detection of cyanide ions and traces of water in acetonitrile supported with voltammetric studies. J Appl Electrochem. 2020;50:185. 10.1007/s10800-019-01382-3.Suche in Google Scholar

[7] Reyes-Cruz V, Gonzalez I, Oropeza MT. Voltammetric evaluation of the electrode material on the oxidation of cyanide catalyzed by copper ions. J Solid State Electrochem. 2005;9:566. 10.1007/s10008-004-0592-z.Suche in Google Scholar

[8] Cardenas-Riojas AA, Cornejo-Herrera AF, Muedas-Taipe G, La Rosa-Toro A, Sotomayor MD, Ponce-Vargas M, et al. Electrochemical sensor based on 1,8-dihydroxyanthraquinone adsorbed on a glassy carbon electrode for the detection of [Cu(CN)3](aq)2− in alkaline cyanide copper plating baths waste. J Electroanal Chem. 2021;880:114909. 10.1016/j.jelechem.2020.114909.Suche in Google Scholar

[9] Breuer PL, Sutcliffe CA, Meakin RL. Cyanide measurement by silver nitrate titration: Comparison of rhodanine and potentiometric end-points. Hydrometallurgy. 2011;106:135. 10.1016/j.hydromet.2010.12.008.Suche in Google Scholar

[10] Kruse JM, Mellon MG. Colorimetric determination of ammonia and cyanate. Anal Chem. 1953;25:1188. 10.1021/ac60080a012.Suche in Google Scholar

[11] Kumar SM, Jothi D, Munusamy S, Enbanathan S, Iyer SK. Imidazole-derived new colorimetric/fluorometric chemosensor for the sensitive recognition of CN− ions: Real-time application in food samples and fluorescence bio-imaging. J Photochem Photobiol A: Chem. 2023;434:114269. 10.1016/j.jphotochem.2022.114269.Suche in Google Scholar

[12] Wang F, Wang L, Chen X, Yoon J. Recent progress in the development of fluorometric and colorimetric chemosensors for detection of cyanide ions. Chem Soc Rev. 2014;43:4312–24. 10.1039/C4CS00008K.Suche in Google Scholar PubMed

[13] Enbanathan S, Manickam S, Munusamy S, Jothi D, Kumar SM, Iyer SK. A phenanthridine-based probe for selective detection of hypochlorite ions. N J Chem. 2022;46:6570–6. 10.1039/D1NJ06023F.Suche in Google Scholar

[14] Zou Q, Tao F, Wu H, William WY, Li T, Cui Y. A new carbazole-based colorimetric and fluorescent sensor with aggregation induced emission for detection of cyanide anion. Dye Pigm. 2019;164:165–73. 10.1016/j.dyepig.2019.01.023.Suche in Google Scholar

[15] Reddy TS, Moon H, Choi MS. Turn-on fluorescent naphthalimide–benzothiazole probe for cyanide detection and its two-mode aggregation-induced emission behavior. Spectrochim Acta Part A Mol Biomol Spectrosc. 2021;252:119535. 10.1016/j.saa.2021.119535.Suche in Google Scholar PubMed

[16] Jain H, Deswal N, Joshi A, Ramachandran C, Kumar R. Triazole-appended pyrano[2,3-c]pyrazolone based colorimetric chemosensors for recognition of Fe3 + ions and their molecular logic gate behavior. Anal Methods. 2019;11:3230–43. 10.1039/C9AY00515C.Suche in Google Scholar

[17] Ghorai P, Pal K, Karmakar P, Saha A. The development of two fluorescent chemosensors for the selective detection of Zn2+ and Al3+ ions in a quinoline platform by tuning the substituents in the receptor part: elucidation of the structures of the metal-bound chemosensors and biological studies. Dalton Trans. 2020;49:4758–73. 10.1039/C9DT04902A.Suche in Google Scholar

[18] Rifai A, Alhaddad N, Noun M, Abbas I, Tabbal M, Shatila R, et al. A click mediated route to a novel fluorescent pyridino-extended calix[4]pyrrole sensor: synthesis and binding studies. Org Biomol Chem. 2019;17:5818. 10.1039/C9OB01106D.Suche in Google Scholar PubMed

[19] Chen W, Guo C, He Q, Chi X, Lynch VM, Zhang Z, et al. Molecular cursor caliper: A fluorescent sensor for dicarboxylate dianions. J Am Chem Soc. 2019;141(37):14798–806. 10.1021/jacs.9b07170.Suche in Google Scholar PubMed

[20] Zhou J, Yu G, Li Y, Shen J, Wang M, Li Z, et al. [2]Pseudorotaxane-based supramolecular optical ındicator for the visual detection of cellular cyanide excretion. Chem Eur J. 2019;25:14447. 10.1002/chem.201903577.Suche in Google Scholar PubMed

[21] Ma X-Q, Wang Y, Wei T-B, Qi L-H, Jiang X-M, Ding J-D, et al. A novel AIE chemosensor based on quinoline functionalized Pillar[5]arene for highly selective and sensitive sequential detection of toxic Hg2+ and CN−. Dye Pigm. 2019;164:279–86. 10.1016/j.dyepig.2019.01.049.Suche in Google Scholar

[22] Dwijenra N, Patra I, Ansari MJ, Saadoon N, Al Mashhadani ZI, Obaid NH, et al. Insights into the electronic properties of coumarins: A comparative study synthesis and characterization of Fe2O3/Mn2O3 magnetic nanocomposites for the photocatalytic degradation of methylene blue. Phys Chem Res. 2023;11(2):437–47. 10.22036/pcr.2022.336018.2070.Suche in Google Scholar

[23] Venkatesan V, Kumar RS, Kumar SKA, Sahoo SK. Highly selective turn-on fluorogenic chemosensor for Zn2 + based on chelation enhanced fluorescence. Inorg Chem Commun. 2019;102:171–9. 10.1016/j.inoche.2019.02.020.Suche in Google Scholar

[24] Halay E, Bozkurt S. Enantioselective recognition of carboxylic acids by novel fluorescent triazine-based thiazoles. Chirality. 2018;30:275–83. 10.1002/chir.22792.Suche in Google Scholar PubMed

[25] Zhao J, Ji S, Chen Y, Guo H, Yang P. Excited state intramolecular proton transfer (ESIPT): from principal photophysics to the development of new chromophores and applications in fluorescent molecular probes and luminescent materials. Phys Chem Chem Phys. 2012;14:8803–17. 10.1039/C2CP23144A.Suche in Google Scholar

[26] Wu Y, Peng X, Fan J, Gao S, Tian M, Zhao J, et al. Fluorescence sensing of anions based on inhibition of excited‐state intramolecular proton transfer. J Org Chem. 2007;72:6270. 10.1021/jo061634c.Suche in Google Scholar PubMed

[27] Kwon JE, Park SY. Advanced organic optoelectronic materials: harnessing excited‐state intramolecular proton transfer (ESIPT) process. Adv Mater. 2011;23:3615–42. 10.1002/adma.201102046.Suche in Google Scholar PubMed

[28] Zhang X, Yin J, Yoon J. Recent advances in development of chiral fluorescent and colorimetric sensors. Chem Rev. 2014;114:4918–59. 10.1021/cr400568b.Suche in Google Scholar PubMed

[29] Qian Y, Li S, Zhang G, Wang Q, Wang S, Xu H, et al. Aggregation‐induced emission enhancement of 2‐(2′‐hydroxyphenyl) benzothiazole‐based excited‐state intramolecular proton‐transfer compounds. J Phys Chem B. 2007;111:5861–8. 10.1021/jp070076i.Suche in Google Scholar PubMed

[30] Hong Y, Lam JWY, Tang BZ. Aggregation‐induced emission. Chem Soc Rev. 2011;40:5361–88. 10.1039/C1CS15113D.Suche in Google Scholar

[31] Gülbaş HE, Bozkurt S, Halay E. Synthesis and characterization of dicarboxamide derivative: Cu2+ selective turn-on fluorometric and colorimetric chemosensor. J Heterocycl Chem. 2023;60(7):1223. 10.1002/jhet.4664.Suche in Google Scholar

[32] Bozkurt S, Halay E. Synthesis, application and AIE properties of novel fluorescent tetraoxocalix[2]arene[2]triazine: The detection of a hazardous anion, cyanate. Tetrahedron. 2020;76:131647. 10.1016/j.tet.2020.131647.Suche in Google Scholar

[33] Alam P, Kachwal V, Laskar IR. A multi-stimuli responsive “AIE” active salicylaldehyde-based schiff base for sensitive detection of fluoride. Sens Actuators B: Chem. 2016;228:539–50. 10.1016/j.snb.2016.01.024.Suche in Google Scholar

[34] Kumar G, Paul K, Luxami V. Aggregation induced emission-excited state intramolecular proton transfer based “off-on” fluorescent sensor for Al3+ ions in liquid and solid state. Sens Actuators B: Chem. 2018;263:585–93. 10.1016/j.snb.2018.02.078.Suche in Google Scholar

[35] Gupta AS, Paul K, Luxami V. A fluorescent probe with “AIE + ESIPT” characteristics for Cu2+ and F− ions estimation. Sens Actuators B: Chem. 2017;246:653–61. 10.1016/j.snb.2017.02.080.Suche in Google Scholar

[36] 4500-CN− CYANIDE− CYANIDE. Standard Methods For the Examination of Water and Wastewater, 23rd. 2018. 10.2105/SMWW.2882.077.Suche in Google Scholar
Received: 2023-09-15
Revised: 2023-11-06
Accepted: 2023-11-20
Published Online: 2023-12-31

© 2023 the author(s), published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

Artikel in diesem Heft

  1. Research Articles
  2. Detection of exosomes in various biological fluids utilizing specific epitopes and directed multiple antigenic peptide antibodies
  3. A green HPLC method for the determination of apixaban in pharmaceutical products: Development and validation
  4. Real-time monitoring of recombinant GFP expression in single-cell Komagataella phaffii through filamentous pelletization technology
  5. Review Articles
  6. Progress of sensitive materials in chemiresistive sensors for detecting chemical warfare agent simulants: A review
  7. Major biochemical constituents of Withania somnifera (ashwagandha) extract: A review of chemical analysis
  8. A brief review of the application of microextraction by packed sorbent for antibiotics analysis from biological, food, and environmental samples
  9. Poly- and per-fluoroalkyl substances in water: Occurrence, analytical methodologies, and remediations strategies: A comprehensive review
  10. Special Issue: Greener Analytical Methods - Part I
  11. Green novel photometric and planar chromatographic assays of remdesivir: Comparative greenness assessment study using estimated GAPI tool versus ISO technical reported methods
  12. Enhancing methane sensing with NDIR technology: Current trends and future prospects
  13. Eco-friendly HPLC method by using response surface design to measure a combination of three antidiabetic drugs
  14. Metal and metalloid monitoring in water by passive sampling – A review
  15. Green chemistry and its implementation in pharmaceutical analysis
  16. Synthesis of a benzothiazole-based structure as a selective colorimetric-fluorogenic cyanate chemosensor
https://doi.org/10.1515/revac-2023-0067
Schlagwörter für diesen Artikel
ESIPT; aggregation-induced emission; cyanate detection; sensor; benzothiazole
Creative Commons
BY 4.0

Artikel in diesem Heft

  1. Research Articles
  2. Detection of exosomes in various biological fluids utilizing specific epitopes and directed multiple antigenic peptide antibodies
  3. A green HPLC method for the determination of apixaban in pharmaceutical products: Development and validation
  4. Real-time monitoring of recombinant GFP expression in single-cell Komagataella phaffii through filamentous pelletization technology
  5. Review Articles
  6. Progress of sensitive materials in chemiresistive sensors for detecting chemical warfare agent simulants: A review
  7. Major biochemical constituents of Withania somnifera (ashwagandha) extract: A review of chemical analysis
  8. A brief review of the application of microextraction by packed sorbent for antibiotics analysis from biological, food, and environmental samples
  9. Poly- and per-fluoroalkyl substances in water: Occurrence, analytical methodologies, and remediations strategies: A comprehensive review
  10. Special Issue: Greener Analytical Methods - Part I
  11. Green novel photometric and planar chromatographic assays of remdesivir: Comparative greenness assessment study using estimated GAPI tool versus ISO technical reported methods
  12. Enhancing methane sensing with NDIR technology: Current trends and future prospects
  13. Eco-friendly HPLC method by using response surface design to measure a combination of three antidiabetic drugs
  14. Metal and metalloid monitoring in water by passive sampling – A review
  15. Green chemistry and its implementation in pharmaceutical analysis
  16. Synthesis of a benzothiazole-based structure as a selective colorimetric-fluorogenic cyanate chemosensor
Jetzt anmelden und 20% sparen
Institutioneller Zugang
Wie funktioniert Authentifizierung?
Haben Sie eine Idee, wie wir unsere Website verbessern können?
Bitte schreiben Sie uns.
© 2025 De Gruyter Brill
Heruntergeladen am 10.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/revac-2023-0067/html
Button zum nach oben scrollen