Abstract
Carbazole-based Schiff bases have emerged as versatile chemosensors for detecting toxic and essential metal ions, addressing critical environmental and health concerns arising from metal pollution. This chapter explores their structural design, emphasizing the integration of the electron-rich carbazole core with imine (‒C=N‒) functionalities, which enhance π-conjugation, thermal stability, and selective metal coordination. Detection of transition metal ions such as Fe3+, Cr3+, Al3+, and Cu2+ has been successfully achieved using carbazole-based Schiff bases with a detection limit up to nanomolar range. Heavy metals, such as Hg and Pb, have also been detected using such materials. These sensors operate
Keywords
- chemosensor
- carbazole
- Schiff base
- metal ion detection
- fluorescent probes
1. Introduction
The increasing industrialization and anthropogenic activities have led to the widespread distribution of heavy and transition metal ions in various ecosystems, posing serious threats to both environmental and human health. Thus, detection of metal ions in environmental and biological systems has emerged as a critical area of research, driven by the dual imperatives of safeguarding human health and preserving ecological balance.
Heavy metals such as mercury (Hg2+), lead (Pb2+), and chromium (Cr3+/Cr6+) are notorious for their toxicity even at trace concentrations, contaminating water supplies, soil, and food chains. Conversely, essential ions like iron (Fe3+), zinc (Zn2+), copper (Cu2+), and cobalt (Co2+) play vital roles in biological processes but become harmful when dysregulated. Traditional analytical methods for metal ion detection, including atomic absorption spectroscopy (AAS) and inductively coupled plasma mass spectrometry (ICP-MS), offer high sensitivity but suffer from limitations such as costly instrumentation, complex sample preparation, and lack of real-time monitoring capabilities. This has spurred interest in developing chemosensors—molecular probes that combine selectivity, sensitivity, and practicality for on-site detection. Among the plethora of sensing platforms, Schiff bases, being dynamic ligands formed
In recent years, Schiff base sensors and their metal ion complexes have gathered significant attention as a prominent research focus, driven by their diverse practical applications across scientific disciplines. These include environmental monitoring and biological cell imaging, where they enable precise detection of target ions within cellular structures, tissues, and organelles [1, 2, 3, 4, 5]. Additionally, their customizable design and multi-stimuli-responsive characteristics make them valuable in optoelectronic systems [6, 7, 8]. The inherent molecular switching behavior of Schiff bases has further been exploited in advanced technologies such as molecular keypads and logic gates [9, 10].
The carbazole moiety, a nitrogen-containing heterocycle with an electron-rich aromatic core, provides a rigid, planar scaffold that enhances π-conjugation, thermal stability, and luminescent properties. When integrated with the imine (‒C=N‒) group, a hallmark of Schiff bases, these hybrid systems exhibit synergistic effects: the carbazole unit amplifies fluorescence or colorimetric signals, while the imine group acts as a selective coordination site for metal ions. This dual functionality enables carbazole-Schiff bases to act as “turn-on” or “turn-off” sensors, with detectable changes in absorption or emission spectra upon metal binding. Moreover, their modular synthesis allows for precise structural modifications, such as introducing electron-donating/withdrawing substituents or extending conjugation, to optimize sensitivity toward specific ions.
Over the past decade, researchers have harnessed these attributes to design carbazole-Schiff base sensors for detecting a wide array of metal ions. For instance, derivatives functionalized with hydroxyl (-OH) or thiol (-SH) groups demonstrate a high affinity for Hg2+, a potent neurotoxin,
Recent innovations, such as incorporating aggregation-induced emission (AIE) motifs or graphene oxide nanocomposites, have further improved detection thresholds, enabling trace-level analysis in complex matrices like wastewater or cellular environments [12, 13]. Although some extensive review articles have addressed the potential of Schiff bases and their derivatives toward metal ion detections, [14, 15, 16, 17, 18] a comprehensive summary specifically addressing the potential of carbazole-based Schiff bases and their use in this context remains absent in the literature.
The current chapter provides a comprehensive exploration of carbazole-based Schiff bases as next-generation metal ion sensors. It begins by elucidating the structural design principles that govern their sensing behavior, emphasizing the interplay between the carbazole core, Schiff base linker, and auxiliary functional groups, with detailed discussion on the mechanisms of ion recognition, mechanisms underlying metal ion recognition, spectroscopic responses including chelation dynamics, electronic interactions, and steric effects, followed by structure-activity relationships.
Through comprehensive literature examples, the emerging trends and opportunities in this rapidly evolving field are identified and highlighted. By reviewing recent literature and critically analyzing structure-property relationships, this chapter aims to inspire innovative approaches to sensor design while bridging the gap between academic research and industrial implementation.
2. Detection of transition metal ions (Fe, Cr, Al, Cu)
Transition metal ions are among the most widely invested metals worldwide. Many industries, such as mining, electronics, and battery manufacturing, release metal ions as waste. They can contaminate water, soil, and food chains if not treated and regulated, causing serious diseases in humans and animals. Strict regulatory limits on metal concentrations by government bodies demand sensitive detection methods, essential for compliance and advancements in sensors, catalysis, and materials science.
2.1 Detection of Fe3+ and Cr3+
Fe3+ is vital for biological processes like oxygen transport and cellular metabolism, but its imbalance (deficiency or excess) leads to disorders such as anemia, organ damage, and diabetes, highlighting the need for precise detection methods to monitor its levels for human health. Li

Figure 1.
The synthetic route of probe 1 (
The fluorescence enhancement of
By increasing the number of nitrogen coordination sites, a much stronger effect can be expected. He

Figure 2.
Synthesis and binding mode of probe P2 with Fe3

Figure 3.
UV response of
Iron detection by imino nitrogen and phenolic oxygen is highly pragmatic, as in another report by Nandhakumar

Figure 4.
Synthesis of
The authors tested
2.2 Detection of Al3+
Aluminum is the third most abundant element in the Earth’s crust, comprising roughly 8% by weight, and is extensively used across industries such as transportation (aircraft, cars), construction (window frames, roofing), packaging (beverage cans, foil), and electrical applications (power lines, wiring) and in many consumer goods like cookware, appliances, and furniture. Exposure to aluminum is usually not harmful, but excessive contact with Al3+ can bioaccumulate in the body and is implicated in neurological disorders (e.g., Alzheimer’s and Parkinson’s disease), kidney damage, chronic renal failure, and bone softening due to its interference with physiological processes [22, 23]. Consequently, developing highly selective and sensitive Al3+ detection methods is essential for monitoring environmental and biological systems and mitigating their adverse health and ecological impacts. A challenge in developing chemosensors for Al3+ is its lower coordination ability than other transition metals, and it is difficult to identify spectroscopically due to its lack of photophysical characteristics. However, O- and N- being strong hetero donor centers could capture Al3+ in soluble form.
Another design similar to

Figure 5.
Synthetic route to probe 4 (
In 90% aqueous CH3CN, the probe
Replacing diiodo salicylaldehyde with naphthaldehyde led to enhanced fluorescence due to extended π-conjugation, as witnessed by a carbazole Schiff-based Al3+ detector, reported by Kaya

Figure 6.
Synthesis and binding mode of probe 5 (
Fluorescence studies revealed an 11-fold emission enhancement at 533 nm upon Al3+ addition, with no significant response to other ions. Competitive experiments confirmed that Al3+ detection remains unaffected in the presence of interfering species, revealing its specificity. The binding stoichiometry between
In another report by Kaya

Figure 7.
Synthetic pathway and binding mechanism of
The LOD was 9.29 × 10−7 M, and K

Figure 8.
Synthetic route toward probe 7 (
This design led to AIEE utilizing ESIPT in THF/H2O mixtures, with enhanced fluorescence observed at 480 nm when the water fraction reached 70%. Upon addition of Al3+, a distinct color change from yellow to colorless was observed under daylight, and an intense blue emission under UV light, indicating a highly selective “turn-on” fluorescence response. Among a panel of metal ions, only Al3+ caused significant spectral changes. Fluorescence and UV-Vis titrations confirmed a 1:1 binding stoichiometry (Job’s plot) and an association constant (K
DFT calculations revealed that the regions with high electronegativity, having the strongest attraction to cations binding sites, were observed around the nitrogen atom of the imine groups (‒C=N‒) and the oxygen of the phenol groups (‒OH) (Figure 9). The binding mechanism was attributed to Al3+-induced hydrolysis of the imine bond, regenerating 2,7-bisformylcarbazole, as confirmed by 1H-NMR spectral shifts and fluorescence quantum yield, which increased from 0.5% (Carb-Azo) to 13.7% (product). Furthermore, a smartphone-assisted fluorometric platform using a fiber-optic endoscope was developed for practical Al3+ detection in drinking water, achieving a detection limit of 0.4 μM. Recovery experiments in spiked commercial water samples gave values from 94.8 to 116.7% with RSDs <12%, validating the practical applicability of both the spectroscopic method and the portable device for real-time environmental monitoring of Al3+ contamination.

Figure 9.
Binding mode of
Inclusion of benzophenone moiety on carbazole not only can extend conjugation but also enhance the photophysical properties of probe overall, owing to its strong electron-accepting and UV-absorbing abilities. Hu and Tao group [28] recently designed an AIE-active Schiff-base probe,

Figure 10.
Synthesis pathway toward probe

Figure 11.
Binding mechanism of
Fluorescence titrations established a linear detection range of 50–500 μM and a low detection limit of 1.486 μM, which is well below the WHO guideline of 7.41 μM. Application to real water samples showed recoveries of 100.72–102.85% with RSD <2.82%, revealing
2.3 Detection of Cu2+
Copper is the third most abundant transition metal in the human body and is vital for the development and function of multiple organs such as the heart, central nervous system, immune system, and liver, yet its dysregulation can lead to disorders like Menkes and Wilson’s diseases when deficient or overloaded [29]. Alongside its biological importance, copper has wide utilization in different industries like conducting wires, batteries, switches, transformers, and telecommunications equipment. Therefore, developing highly sensitive and selective chemosensors for trace Cu2+ detection is critical. Recent advances in fluorescent probes demonstrating “turn-on” mechanisms and detection limits in the micromolar to sub-micromolar range envisaged the idea of π-bridging between molecules to make their absorption and emission bands red-shifted, and then the color variation can be observed and determined via naked eyes [30, 31]. In view of this concept, Zhu and Fang

Figure 12.
Synthetic route of

Figure 13.
Sensing mechanism and binding of
In fluorescence spectroscopy, a bright-yellow fluorescence (λex = 420 nm, λem = 520 nm) was observed, which was selectively and dramatically quenched by Cu2+ ion, accompanied by a visible color change from yellow-green to colorless, while other metal ions induced negligible spectral changes. UV-Vis titrations and Benesi-Hildebrand analysis revealed an association constant Ka = 1.47 × 105 M−1 and a 1:1 P9-Cu2+ stoichiometry (confirmed by Job’s plot), with a fluorescence-based detection limit of 1.14 × 10−5 M; the rapid (≤30 s) and reversible (
Gosh
Among the different metal ions (Hg2+, Ag+, Fe2+, Cu2+, Fe3+, Pb2+, Cd2+, Al3+, Ca2+, Ni2+, and Co2+) tested, the gel underwent a gel-to-sol transition upon addition of ≥0.5 equiv. Cu2+ or Fe3+ in DMF/H2O as solvent. Subsequent treatment with F− distinguished Fe3+ (greenish-yellow) from Cu2+. The solution phase sensing showed a π–π* absorption at 455 nm and green emission at 520 nm; both were selectively quenched by Cu2+ and Fe3+ (other ions inert). Job’s plots indicated a 1:2 (M/P10) stoichiometry, and emission titrations yielded binding constants for Cu2+ and Fe3+ as K

Figure 14.
Synthetic route to
The conjugation can be extended

Figure 15.
Synthetic route to

Figure 16.
Binding mechanism of
In another report by Mishra

Figure 17.
Synthesis of bis-carbazole-based probe
Copper detection has been widely explored using carbazole-based Schiff bases. Another article by Hu and Tao

Figure 18.
Synthetic route for
Upon Cu2+ binding, chelation-enhanced quenching (CHEQ) occurred due to the paramagnetic nature of Cu2+, resulting in a “turn-off” response. Job’s plot analysis revealed a 1:2 binding stoichiometry (
In recent years, large biological molecules, specifically steroids, have attracted great attention in ion recognition, due to their amphiphilic and structurally rigid conformations. Carbazole and cholic acid naturally exhibit compatibility, having a rigid structure. Additionally, the hydroxyl groups present in cholic acid can facilitate subsequent derivatization, and sensors based on cholic acid could be used under physiological conditions due to biocompatibility. In such a report by Mishra

Figure 19.
Synthesis of

Figure 20.
Binding mode of
3. Detection of heavy metal ions (Hg, Pb)
Detecting heavy metal ions is crucial due to their significant impact on human health, environmental safety, and industrial processes. Many heavy metals, such as lead, mercury, and cadmium, are highly toxic even at low concentrations and can accumulate in living organisms, causing serious diseases. Industrial activities often release these ions into water, soil, and air, making their monitoring essential to prevent ecological damage. Strict regulations on heavy metals in water and food drive the need for sensitive, selective, and rapid detection methods for environmental, healthcare, and technological applications.
3.1 Detection of Hg2+
Mercury is a pervasive industrial contaminant used in sectors such as petroleum refining, chemical industry, pharmaceuticals, pulp papermaking, and electronics. It bioaccumulates in brain tissues, leading to neurological damage once critical concentrations are reached. Thiourea moiety is widely used in the field of molecular recognition, especially for heavy metal ions, because of its three coordinating sites, two nitrogen atoms, and one sulfur atom (H2NCSNH2). The sulfur group has a special affinity for mercury, as the name mercapto for -SH group comes from the Latin words “

Figure 21.
Synthesis and binding mode of
Replacing amino groups with hydrazine and including heterocyclic aromatics not only increases the power of the coordination site but also the extension of π-conjugation. The article by Sekar

Figure 22.
Synthesis of
The sensor exhibited a turn-on fluorescence response at 433 nm upon Hg2+ binding, driven by an ICT mechanism from the carbazole donor to the benzothiazole acceptor. UV-Vis and fluorescence titration confirmed selectivity for Hg2+ over 16 competing metal ions, with a 1:1 binding stoichiometry (Job’s plot) and a binding constant K

Figure 23.
Fluorescence spectrum and binding mechanism of probe
The thiol (-SH) group can be replaced by pyridine/quinoline nitrogen in the vicinity of methylenehydrazine to serve as a coordinating site for Hg2+ ions. The advantage of introducing quinoline moiety is to enhance the fluorescence capacity and quantum yield of designed probe. To this approach, Singh

Figure 24.
Synthetic route to probe
Single-crystal XRD analysis revealed that
Fluorescence titration and Job’s plot analyses confirmed a 1:1
3.2 Detection of Pb2+
Recently, Schiff base formation has also become a foundation reaction for making COFs. Carbazole remains at the core of COFs materials, where the Schiff base reaction is being used to construct these 2-D or 3-D materials. The excellent crystallinity, porosity, and tunable pore size of COFs are among the ideal properties for metal ions detection and adsorption.
A carbazole-grafted covalent organic framework (COF-CB) was synthesized by Wang

Figure 25.
Structure of carbazole-based COF and binding mechanism with Pb2+.
The above one is just an example of carbazole-based Schiff base COFs materials’ potential toward metal ion detection; there are many exciting carbazole-based Schiff base COFs, for the selective and sensitive detection of metal ions. Since this topic deviates from the title of chapter so COFs are not discussed here.
4. Conclusions
So, the bottom line is that carbazole-based Schiff-base chemosensors unite synthetic simplicity with versatile photo-physics. By tuning the donor/acceptor balance, harnessing PET/CHEF/AIE/ESIPT mechanisms, and integrating user-friendly formats (gels, strips, smartphone read-outs), detection limits can be pushed into the nM range, to achieve rapid “turn-on” selectivity in real water samples. For common transition metals such as Fe, Cr, Cu, Al, etc., imine nitrogen (C=N) alongside other donor groups like -OH, -SH, NH2, NR2, etc. are ideal as coordinating sites while incorporating carbazole and naphthalene moieties enhance photophysical and fluorescence properties in the designed chemosensor. For heavy metals (Hg, Pb, As), the utilization of carbazole-based COFs and MOFs and nanomaterials especially nanofibers could be designed to detect such metals in the nM range. As global concerns over metal pollution and metabolic disorders escalate, carbazole-Schiff bases stand poised to play a pivotal role in advancing affordable, rapid, and reliable detection technologies.
5. Future perspectives
Although carbazole-Schiff bases could be promising candidates for developing chemosensors for a variety of sensing applications, because of their ease of formation and stapling of two moieties of tunable characteristics together, their labile hydrolysis and water sensitivity remains a challenge. In addition, the Lewis acidic behavior and catalysis ability of transition metal ions promote the Schiff bases hydrolysis in both aqueous and organic/aqueous solvents. However, a strategically designed configuration of binding sites and signaling gears holds the potential to yield a chemosensor capable of detecting the metal ions in aqueous or organic/aqueous media. So next-generation carbazole-based Schiff base sensors can utilize a push-pull architecture by combining strong donors (dialkylamino) with extended acceptors (dicyanovinyl, nitrophenyl) to red-shift absorption/emission toward the visible/NIR. To overcome water solubility problem sulfonate or poly(ethylene glycol) moieties can be introduced to eliminate organic cosolvent for sensing in full aqueous media. Integration of emerging techniques like nanostructured assemblies the sensor materials can be imbedded in paper strips, hydrogels, or nanofibers for simple dip-test, on-site colorimetry, or “dipstick” fluorescence methods.
Despite these advances, translating laboratory-scale discoveries into commercial sensors remains a challenge. Key hurdles include long-term stability under varying pH and temperature conditions, reducing synthesis costs, and integrating these materials into user-friendly devices such as paper-based strips or portable fluorimeters. However, progress in nanotechnology and materials engineering, such as embedding carbazole-Schiff bases into polymer matrices or metal-organic frameworks (MOFs) offers promising pathways to enhance durability and scalability. Additionally, collaborations between academia and industry are critical to validate sensor performance in real-world scenarios, from monitoring industrial effluents to diagnosing metal imbalances in clinical settings.
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