Recent developments in fluorescent and colorimetric chemosensors based on schiff bases for metallic cations detection: A review

doi:10.1016/j.jece.2021.106381

Journal of Environmental Chemical Engineering

Volume 9, Issue 6, December 2021, 106381

https://doi.org/10.1016/j.jece.2021.106381 Get rights and content

Highlights

•
This review covers a wide range of Schiff bases used for chemosensing of metal ions.
•
The selectivity and sensitivity of the Schiff bases for metal ions are summarized.
•
The performance of Schiff bases in comparison with other chemosensors is discussed.
•
Different analytical parameters for the analysis of heavy metal ions are reviewed.

Abstract

Hugo Schiff (1864), was the first who synthesized Schiff bases by the condensation reaction of primary amines with carbonyl compounds (aldehyde or ketone). Schiff bases display several structural and electronic features that allow their application in different fields, ranging from medicinal to chemosensing. Schiff bases coordinate with various metal ions and form stable complexes. Due to their excellent coordination ability, Schiff bases are used as fluorescent turn-on/turn-off and colorimetric chemosensors for the detection of different metal cations including Ag⁺, Cu²⁺, Co²⁺, Mn²⁺, Cd²⁺, Hg²⁺, Ni²⁺, Zn²⁺, Pd²⁺, Fe³⁺, and Al³⁺ in different samples. This review article covers a wide range of Schiff bases used in chemosensing applications for various metal ions (e.g., monovalent, divalent and trivalent cations) in different biological, agricultural and environmental media.

Graphical Abstract

Introduction

Metallic cations are extensively used in different fields and some of these regulate thousands of biological processes that support life. However, the excess of these ions can cause one of the most serious environmental problems because they are non-biodegradable and can accumulate in food chain, which poses a severe threat to the environment and human health even at low concentrations [1], [2]. These ions can cause various health problems including allergy, lung injury, anemia, kidney failure, neurotoxicity, genotoxicity, oxidative toxicity, steroidogenic toxicity, sperm toxicity, apoptotic toxicity and axillary toxicity [3], [4], [5], [6], [7], [8], [9], [10], [11]. Therefore, it is highly desired to develop an efficient method for the determination of these ions in different samples. Hence, various methods such as liquid chromatography[12], electrochemical [13], voltammetric [14], reversed phase-high-performance liquid chromatography [15] and inductively coupled plasma-mass spectrometry [16] have been developed for the detection of metallic cations. Although these techniques are highly efficient but still suffer from some limitations such as, being expensive and complicated in operation and require excessive sample pretreatment. Alternatively, fluorescent and colorimetric chemosensors have been proposed for the detection of metallic cations to overcome the afore-mentioned limitations of these methods. Spectrofluorometric and colorimetric chemosensors showed high sensitivity and selectivity toward various species (Cations, anions and netural species) [17], [18], [19], [20], [21], [22], [23], [24], [25], [26]. Particularly, chemosensors based on Schiff bases have demonstrated excellent performance for the determination of various metallic cations owing to their facile and inexpensive synthesis, and their ability to coordinate with almost all metal ions and stabilize them in a variety of oxidation states [27]. Besides, these Schiff bases have exhibited a broad range of biological applications including anticancer, antibacterial, analgesic, antifungal, anti-inflammatory, antiviral, antioxidant, antimalarial, antiglycation, and anti-ulcerogenic properties [28]. Many of these compounds have excellent catalytic efficiency in different reactions [20], [21]. In this review article, different Schiff bases have been reviewed as a fluorescent turn-on/turn-off and colorimetric chemosensor for the detection of various metal ions in different matrices. Furthermore, the synthetic routes and sensing mechanisms of different Schiff base chemosensors have been discussed. Finally, the performances of Schiff base chemosensors have been compared with some other reported chemosensors. We hope that this review article will help researchers in designing simple, highly effective and sensitive chemosensors for the detection of various metal ions (e.g., monovalent, divalent and trivalent cations) in different biological, agricultural and environmental media.

Section snippets

Synthesis of Schiff bases

Several synthetic routes have been applied for the syntheses of Schiff bases. Here only a few simple synthetic routes are outlined for the guidance of learners and those who do not deal with organic synthetic chemistry. Hugo Schiff (1864), was the first who synthesize Schiff bases by the reaction of primary amines with aldehyde or ketone under azeotropic distillation (Compound a, Scheme 1) [30]. Different catalysts including acetic acid, p-toluene sulphonic acids, montmorillonite, acid resin,

Schiff bases as chemosensors for detection of toxic metal ions

Several chemosensors based on Schiff bases have been synthesized and used for fluorescent turn-on/turn-off and colorimetric detection of various metal cations (Table 1). There are some concepts to be kept in mind before using these compounds as chemosensors. The incorporation of bulky chains is preferred to obtain a heterogeneous system in an aqueous medium. This enables the establishment of a system for easy and economic separation. Furthermore, in the field of chemosensing, spectroscopic

Sensing mechanism, selectivity and sensitivity of Schiff base chemosensor

Several factors regulate the selectivity and high sensitivity of Schiff base chemosensors, such as the suitable radius of metal ions, the charge on the metal ion, electroni configuration of both the ligand and the metal ion and the structural rigidity and the binding ability of the Schiff base chemosensor with the metal ion [27], [38]. Consequently, different mechanisms have been proposed for the interaction between metal ions and various chemosensors, including chelation-enhanced fluorescence

Detection of monovalent cations

Monovalent cations are involved in different biological processes in human body [39]. However, the excess amount of these metal ions can cause various harmful effects such as neurotoxicity, skin and eye irritation, allergic contact dermatitis, genotoxicity, renal, hepatic, and hematological effects [40], [41]. Mostly, Schiff base chemosensors have been widely applied for the detection of monovalent Ag. Hence, we discussed some selected examples of Schiff base chemosensors for Ag^＋ ions.

Silver

Detection of divalent cations

Among inorganic materials, divalent cations regulate thousands of biological processes that support life [45], [46]. However, oversupply of these ions can cause various health problems including allergy, lung injury, anemia, kidney failure, prenatal brain damage, Wilson’s, prion, Parkinson’s, Alzheimer’s, and epilepsy [47], [48], [49].

Detection of trivalent cations

Trivalent cations play an important role in different biological processes as they have a remarkable ecological, toxicological and physiological impact on the biological and environmental systems. Hence, the sensitive and selective detection of these ions in biological, environmental and agriculture matrices has gained considerable attention.

Performance evaluation

In this review article, we discussed spectrofluorometric and spectrophotometric methods for the detection and determination of different cations in different environmental, biological and agriculture samples. Many of these chemosensors have shown high sensitivity and selectivity for particular analytes with a very low detection limit. The performance of different chemosensors based on Schiff bases for the detection of various cations is discussed. The detection limit values were compared and

Comparison of the performance of Schiff base chemosensors with other chemosensors

Different types of spectrofluorometric and colorimetric chemosensors have been reported for the determination of various metal ions [94], [95], [96], [97], [98], [99], [100], [101], [102], [103]. In this subsection the performances of Schiff base chemosensors were compared with some other reported organic chemosensors including cellulose-based colorimetric chemosensor 49 containing thiourea moiety [104], pyrene appended bis-triazolylated 1,4-dihydropyridine 50 [105], indole-based fluorescent

Conclusion and future perspective

Schiff bases are biologically active organic compounds and have a wide range of applications including anticancer, antibacterial, antifungal, antioxidant, antimalarial, antiglycation, anti-inflammatory, anthelminthic, anti-ulcerogenic, antiviral and analgesic properties. These compounds can be easily prepared in laboratories through different reaction protocols. Schiff bases have been applied for the detection of various metal ions including Ag⁺, Cu²⁺, Co²⁺, Mn²⁺, Cd²⁺, Hg²⁺, Ni²⁺, Zn²⁺, Pd²⁺,

Declaration of Competing Interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Acknowledgments

This work has been financially supported by the Wenzhou University China scientific research start-up fund (QD2021155).

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Recent developments in fluorescent and colorimetric chemosensors based on schiff bases for metallic cations detection: A review

Highlights

Abstract

Graphical Abstract

Introduction

Section snippets

Synthesis of Schiff bases

Schiff bases as chemosensors for detection of toxic metal ions

Sensing mechanism, selectivity and sensitivity of Schiff base chemosensor

Detection of monovalent cations

Detection of divalent cations

Detection of trivalent cations

Performance evaluation

Comparison of the performance of Schiff base chemosensors with other chemosensors

Conclusion and future perspective

Declaration of Competing Interest

Acknowledgments

J. Environ. Manag.

Environ. Nanotechnol. Monit. Manag.

J. Mol. Liq.

Talanta

Biosens. Bioelectron.

J. Electroanal. Chem.

Coord. Chem. Rev.

Tetrahedron Lett.

Coord. Chem. Rev.

Coord. Chem. Rev.

TrAC - Trends Anal. Chem.

Int. J. Biol. Macromol.

J. Organomet. Chem.

J. Mol. Catal. A Chem.

Coord. Chem. Rev.

Environ. Int.

Sens. Actuators B Chem.

J. Photochem. Photo A

Trends Biochem. Sci.

Neurosci. Biobehav. Rev.

Neurosci. Biobehav. Rev.

Microchem. J.

Dyes Pigment.

Sens. Actuators B Chem.

Tetrahedron Lett.

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Tetrahedron Lett.

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Talanta

Spectrochim. Acta Part A Mol. Biomol. Spectrosc.

Sens. Acuators B Chem.

Spectrochim. Acta Part A Mol. Biomol. Spectrosc.

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Talanta

Spectrochim. Acta A Mol. Biomol. Spectrosc.

Polyhedron

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Talanta

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J. Pharm. Biomed. Anal.

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Tetrahedron Lett.