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Article

AIPE-Active Fluorophenyl-Substituted Ir(III) Complexes for Detecting Trinitrophenols in Aqueous Media

by
Jiahao Du
1,
Ruimin Chen
1,
Xiaoran Yang
1,
Xiaona Li
2,* and
Chun Liu
1,*
1
State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China
2
Key Laboratory of Industrial Ecology and Environmental Engineering (MOE), School of Environmental Science and Technology, Dalian University of Technology, Dalian 116024, China
*
Authors to whom correspondence should be addressed.
Chemosensors 2025, 13(8), 315; https://doi.org/10.3390/chemosensors13080315
Submission received: 8 July 2025 / Revised: 12 August 2025 / Accepted: 18 August 2025 / Published: 20 August 2025
(This article belongs to the Special Issue Recent Advances in Chemical Sensors in Dalian University of Technology: Fundamental Science and Applications)
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Abstract

Three fluorophenyl-substituted cyclometalated Ir(III) complexes (Ir1–Ir3) have been synthesized by changing the position of the fluorine atom. All complexes exhibit distinct aggregation-induced phosphorescence emission (AIPE) characteristics in CH3CN/H2O and demonstrate satisfactory detection performance for 2,4,6-trinitrophenols (TNPs) with limits of detection of 124 nM, 101 nM, and 127 nM, respectively. In addition, Ir1–Ir3 possess excellent selectivity and anti-interference capability for TNP detection, showing outstanding performance even in different common water samples. The ultraviolet–visible absorption spectra and luminescence lifetimes of the complexes show that their quenching processes include both a static process and dynamic process, and the detection mechanism may be assigned to a combination of photo-induced electron transfer and an inner-filter effect.

Graphical Abstract

1. Introduction

In 2001, Tang et al. proposed a new concept of aggregation-induced emission (AIE) [1]. In contrast to the aggregation-caused quenching (ACQ) phenomenon, the AIE phenomenon demonstrates that some molecules can significantly enhance their luminescence in aggregated states. The introduction of the AIE notion has broadened the range of applications for luminescent materials, and provides new direction for the development of luminescent materials [2,3,4,5,6]. In 2002, Mani et al. first discovered the phenomenon of aggregation-induced phosphorescence emission (AIPE) in transition metal complexes [7]. Compared to traditional luminescent molecules, transition metal complexes have the advantages of longer phosphorescence lifetime, higher quantum yield, and larger Stokes shift. Currently, studies on the AIPE properties of transition metal complexes have received a broad range of attention [8,9,10].
Ir(III) complexes possess excellent photothermal stability, adjustable luminescence characteristics, and high luminescence efficiency [11,12,13,14,15]. These make them valuable for applications in optoelectronic devices [16], biological imaging and therapy [17], and catalytic science [18]. In 2008, Zhao et al. reported AIPE-active Ir(III) complexes for the first time [19]. Subsequently, a series of AIPE-active Ir(III) complexes have been developed [20,21,22]. Recently, the use of Ir(III) complexes with AIPE properties as probes for monitoring environmental parameters, including organic pollutants [23], pH [24], and toxic gases [25], has received significant attention.
2,4,6-Trinitrophenol (TNP) is a type of nitro compound with powerful explosive properties and high sensitivity to temperature, friction, and impact. At the same time, it has a broad range of industrial applications, such as pharmaceuticals, leather processing, and raw materials for dyes and pigments [26,27]. However, it also pollutes the environment by entering the ecosystem through the medium of water, leading to soil and groundwater contamination [28,29]. Since TNP may persist in the environment, especially when TNP residues contaminate drinking water and agricultural land, it can directly affect human and animal health. Therefore, a highly sensitive, selective, and trace detection method for of TNP is urgently needed. Recently, the detection of TNP in aqueous media using Ir(III) complexes as sensors has attracted extensive interest [30,31,32]. However, the relationship between the molecular structures of the complexes and the detection performances, as well as the detection mechanism for TNP, still require further exploration.
In the past several years, our team has developed a series of Pt(II), Ir(III), and Ru(II) complexes for TNP detection [33,34,35]. We found that introducing a fluorophenyl group can significantly affect the AIPE properties and TNP detection performances of the corresponding Pt(II) complexes [35]. In this work, three fluorophenyl-substituted cyclometalated Ir(III) complexes, Ir1–Ir3, were synthesized and their properties were systematically studied in detail. The results indicate that Ir1–Ir3 are all AIPE-active and demonstrate high selectivity and sensitivity for the detection of TNP in aqueous media, showing great potential as probes for TNP detection.

2. Materials and Methods

2.1. Materials and Instruments

Additional information for the instruments and materials used in this study can be seen in the Supporting Information.

2.2. Synthesis and Characterization of Complexes

Three fluorophenyl-substituted C^N ligands were synthesized according to the reported method (Figure S1) [36]. The Ir(III) complexes were synthesized by the following routes (Scheme 1): IrCl3·3H2O (0.2 mmol, 70.5 mg) and the C^N ligand (0.5 mmol, 124.5 mg) were added to a mixed solution of EtOCH2CH2OH (9 mL) and H2O (3 mL). The mixture was stirred for 24 h at 120 °C under N2 to provide the dichlorobridge intermediate. Subsequently, the intermediate and 2,2′-bipyridine (0.6 mmol, 93.7 mg) were transferred into EtOCH2CH2OH (12 mL) and the mixture was stirred for 24 h at 120 °C under N2. At the end of the reaction, the reaction system was cooled to room temperature. An excess of saturated aqueous solution of KPF6 (1.2 mmol, 220.9 mg) was added into the reaction system and the mixture was stirred at room temperature for 12 h. Finally, the target products of Ir1–Ir3 were isolated and purified by column chromatography. The comprehensive characterizations for Ir1–Ir3 are given in the Supporting Information (Figures S2–S13).
Ir1. An orange-yellow solid, 168.3 mg, yield: 85%. 1H NMR (400 MHz, DMSO-d6) δ 8.91 (d, J = 8.4 Hz, 2H), 8.31 (t, J = 7.7 Hz, 4H), 8.07–7.93 (m, 6H), 7.75 (t, J = 7.6 Hz, 2H), 7.70 (d, J = 5.9 Hz, 2H), 7.34–7.29 (m, 4H), 7.28–7.17 (m, 8H), 6.42 (d, J = 2.4 Hz, 2H).13C NMR (151 MHz, DMSO-d6) δ 166.25, 159.80, 158.16, 155.33, 150.06, 149.87, 148.97, 143.51, 139.64, 138.80, 136.31, 131.04, 131.01, 130.26, 130.24, 129.47, 129.42, 128.72, 128.00, 127.92, 125.04, 125.00, 124.76, 124.74, 124.03, 122.99, 120.28, 116.16, 116.01. 19F NMR (470 MHz, DMSO-d6) δ −69.39, −70.90, −117.53. HRMS (ESI, m/z): calcd for C44H30N4F2Ir [M-PF6]+: 845.2068, found: 845.2061.
Ir2. An orange-yellow solid, 182.2 mg, yield: 92%. 1H NMR (400 MHz, DMSO-d6) δ 8.91 (d, J = 8.3 Hz, 2H), 8.36 (d, J = 8.2 Hz, 2H), 8.29 (t, J = 7.9 Hz, 2H), 8.01 (dd, J = 11.6, 7.4 Hz, 6H), 7.74 (t, J = 5.3 Hz, 4H), 7.38 (td, J = 8.2, 4.0 Hz, 4H), 7.23 (t, J = 6.7 Hz, 2H), 7.18–7.08 (m, 6H), 6.41 (d, J = 2.0 Hz, 2H). 13C NMR (151 MHz, DMSO-d6) δ 166.20, 163.19, 161.58, 155.30, 150.83, 150.12, 149.18, 143.89, 142.55, 142.50, 139.86, 139.62, 138.83, 130.74, 130.69, 128.73, 128.58, 125.50, 124.96, 124.08, 122.34, 122.32, 121.33, 120.36, 114.25, 114.11, 113.01, 112.86. 19F NMR (470 MHz, DMSO-d6) δ −69.39, −70.90, −112.68. HRMS (ESI, m/z): calcd for C44H30N4F2Ir [M-PF6]+: 845.2068, found: 845.2065.
Ir3. An orange-yellow solid, 178.2 mg, yield: 90%. 1H NMR (400 MHz, DMSO-d6) δ 8.91 (d, J = 8.3 Hz, 2H), 8.30 (q, J = 8.0 Hz 4H), 7.99 (q, J = 8.0 Hz, 6H), 7.72 (t, J = 6.6 Hz, 4H), 7.37–7.31 (m, 6H), 7.21 (t, J = 8.1 Hz, 6H), 6.39 (s, 2H). 13C NMR (151 MHz, DMSO-d6) δ 165.80, 162.10, 160.48, 154.80, 150.41, 149.54, 148.55, 142.73, 139.82, 139.11, 138.29, 136.01, 136.00, 128.22, 128.05, 127.77, 127.72, 124.99, 124.45, 123.41, 120.64, 119.71, 115.18, 115.04. 19F NMR (470 MHz, DMSO-d6) δ −69.39, −70.90, −115.05. HRMS (ESI, m/z): calcd for C44H30N4F2Ir [M-PF6]+: 845.2068, found: 845.2064.

2.3. Tests for the Detection of TNP

Stock solutions of each of Ir1–Ir3 (c = 100 μM) were prepared in CH3CN. Then, eight 3 mL suspensions were prepared by taking the stock solution (v = 300 μL) and adding different volumes of CH3CN and H2O. In this way, suspensions with different water contents (0–90%, c = 10 μM) were prepared. For each suspension, 3 mL of them was placed into quartz cuvettes, and then the emission spectra were recorded to study the properties of Ir1–Ir3.
The suspensions of Ir1–Ir3 (Ir1: fw = 60%, Ir2: fw = 70%, Ir3: fw = 70%, in CH3CN/H2O) were prepared in volumetric flasks (200 mL). Then, 11 blank suspension samples of Ir1–Ir3 were randomly selected, and their emission spectra were measured after equilibrium. TNP solutions, with concentrations varying from 0.1 to 20 mM, were prepared in CH3CN/H2O. The TNP solutions (30 μL) at different concentrations were added to the Ir1–Ir3 suspensions (3 mL), and the emission spectra were recorded after allowing the system to equilibrate. In the experiments on selectivity and competition for the detection of TNP, seven analytes with structures partially similar to TNP were selected for testing. The analytes included: 4-Methoxyphenol (MEHQ), 2-Nitrotoluene (2-NT), Nitromethane (NM-55), Phenol, 2-Cresol, 3-Cresol, and 4-Cresol. During the testing process, 30 μL (c = 20 mM) of the analytes was added to each of the Ir1–Ir3 suspensions. To further investigate the anti-interference capability of Ir1–Ir3, 30 μL (c = 20 mM) of eight common ionic compounds was added to each complex suspension. The ionic compounds included the following: KF, KBr, NaOAc, ZnCl2, CaCl2, NiCl2, CuSO4, and CoCO3. Finally, lake water, rainwater, seawater, and tap water were selected for testing in place of deionized water to assess the universality of the complexes in different common water samples. The lake water was collected from Lingshui Lake at Dalian University of Technology, the seawater was collected from Qixianling, Dalian, and the tap water was collected from Dalian University of Technology.
Be cautious! Nitroaromatic compounds are explosive and should be processed in small amounts in a well-ventilated environment. Avoid exposure to high temperatures, open flames, and impact. Always wear appropriate protective equipment.

3. Results and Discussion

3.1. Photophysical Properties

The photophysical properties of Ir1–Ir3 were tested by UV–vis absorption and emission spectrometers. The UV–vis absorption spectra of Ir1–Ir3 exhibit strong absorption bands at 220–320 nm (Figure 1a), which is probably related to the π-π* transitions in the ligand center. Additionally, weak absorption features are observed at wavelengths of 380–450 nm, likely originating from metal-to-ligand charge transfer (MLCT) and ligand–ligand charge transfer (LLCT) [37]. Figure 1b shows the normalized emission spectra of Ir1–Ir3 in CH3CN, and their maximum emission wavelengths are 574 nm, 573 nm, and 578 nm, respectively. More data about the photophysical properties of Ir1–Ir3 can be found in Table S1 of the Supporting Information.

3.2. AIPE Properties and Stability Testing

The luminescence properties of Ir1–Ir3 were initially tested by recording their emission spectra in CH3CN/H2O with different water contents. As shown in Figure 2, there is a significant enhancement of the emission intensities with an increase in water content from 0% to 70%. We speculate that the addition of water, as a poor solvent, causes the aggregation of the complex molecules, thus they exhibit good AIPE properties. Subsequently, dynamic light scattering (DLS) experiments were performed to verify whether Ir1–Ir3 had undergone aggregation (Figure S14 in Supporting Information). It can be seen that Ir1–Ir3 indeed produce aggregates at the selected water contents (Ir1: fw = 60%, Ir2: fw = 70%, Ir3: fw = 70%), and their hydrodynamic diameters are 20.96 nm, 57.36 nm, and 51.33 nm, respectively. The above results confirm that Ir1–Ir3 exhibit significant AIPE properties.
Then, the stabilities of Ir1–Ir3 were analyzed by their emission spectra. The results show that Ir1–Ir3 reach equilibrium after 8 h, 7 h, and 4 h, respectively (Figure 3). Then, the emission spectra of 11 blank suspensions of the complexes were tested after equilibrium to calculate the standard deviations (Table 1).

3.3. Sensing of TNP

Ir1–Ir3 exhibit significant AIPE properties, which indicates their potential to act as probes for detecting TNP. Therefore, we prepared suspensions of Ir1–Ir3 in CH3CN/H2O (Ir1: fw = 60%, Ir2: fw = 70%, Ir3: fw = 70%), and performed TNP titration tests after reaching equilibrium (illustrated in Figure 4). The results show that as the concentration of TNP increases, the emission intensities of Ir1–Ir3 significantly decrease. The quenching efficiencies of Ir1–Ir3 are 18%, 22%, and 17%, respectively, at a TNP concentration of 8 μM (0.8 equiv.). When the TNP concentration increases to 200 μM (20.0 equiv.), the quenching efficiencies of Ir1–Ir3 all exceed 95%. To calculate the quenching constants (KSV) for the detection of TNP, the ratios of the emission intensities before the addition of TNP (I0) to the emission intensities after the addition of TNP (I) were plotted (Figure 4). The Stern–Volmer curves for Ir1–Ir3 are overall non-linear. But at low concentrations of TNP (0–8 μM), the I0/I ratios of Ir1–Ir3 exhibit a clear linear relationship, indicating that it is a static quenching process. The Stern–Volmer plots show a non-linear relationship with increasing concentrations of TNP. This indicates that the luminescence quenching process involves both static and dynamic quenching [38]. According to the Stern–Volmer equation (I0/I = KSV[Q] + 1), the quenching constants for Ir1–Ir3 were obtained in the low concentration range through fitting, with values of 2.7 × 104 M−1, 3.3 × 104 M−1, and 2.3 × 104 M−1, respectively.
Within the low concentration range (0–8 μM), linear regression analyses are performed on the emission intensities of Ir1–Ir3 to calculate their slopes K (Figure 5). The limits of detection (LODs) for Ir1–Ir3 are calculated according to the formula LOD = 3σ/|K|, with values of 124 nM, 101 nM, and 127 nM, respectively. Compared to the previously reported complexes [39,40,41], Ir1–Ir3 exhibit extremely low LODs, demonstrating excellent performance for the detection of TNP (Table S2 in Supporting Information).

3.4. Selectivity and Anti-Interference Capability Experiments

First, selective and competitive experiments were performed on Ir1–Ir3. Seven analytes (MEHQ, 2-NT, NM-55, Phenol, 2-Cresol, 3-Cresol, and 4-Cresol) were individually added to Ir1–Ir3 suspensions. The emission spectra before and after the addition of TNP were tested. The results show that the addition of these analytes has little effect on the luminescence of the complex samples (<6% for all analytes except 2-NT, which is approximately 20%), and there are small changes in emission intensities (Figure 6). The luminescence quenching rates of all samples exceed 94% after the addition of TNP. In summary, the effects of other analytes on the emission intensities of the samples are much smaller than those of TNP, and Ir1–Ir3 show excellent selectivity for TNP.
Next, an in-depth study was conducted on the anti-interference capability of Ir1–Ir3. Eight common ionic compounds (KF, KBr, NaOAc, ZnCl2, CaCl2, NiCl2, CuSO4, and CoCO3) were individually added to Ir1–Ir3 suspensions, and the emission spectra before and after the addition of TNP were tested as well. The results show that the addition of common ionic compounds has a negligible effect on the emission intensities and a minimal effect on the quenching efficiencies of Ir1–Ir3 (<7% for all compounds; Figure 7). Furthermore, the luminescence quenching effects of the samples are not affected by these ionic compounds after the addition of TNP, and the luminescence quenching rates reach over 94% in all cases. These experimental results indicate that Ir1–Ir3 show outstanding anti-interference capability when used for the detection of TNP. They effectively avoid effects from common ionic compounds, ensuring the accuracy and reliability of the detection results.
Finally, the emission spectra of Ir1–Ir3 were tested using lake water, rainwater, seawater, or tap water in place of deionized water. This was to assess the universality of Ir1–Ir3 for the detection of TNP. The results show that the emission intensities of Ir1–Ir3 are not affected by different water samples after the addition of TNP, and they still show excellent selectivity for TNP (Figure 8). The quenching effects in different water samples are similar to those in deionized water, and the quenching rates still reach over 94%. This indicates that despite the differences in water quality, Ir1–Ir3 not only exhibit remarkable stability and efficiency but also demonstrate an excellent ability to detect TNP in different environments, showing great potential for applications.

3.5. Sensing Mechanism

There are two common types of luminescence quenching process: one is static quenching and the other is dynamic quenching [42]. Static quenching refers to the interaction between the luminescent molecules and the quenchers, forming non-luminescent ground-state complexes [43]. These complexes inhibit the luminescence of the luminophores, leading to a decrease in their intensities. Dynamic quenching refers to the process in collisions between the luminophores and the quenchers, which lead to energy or a charge transfer [44]. Dynamic quenching is usually a rapid process and its rate is influenced by the concentration of quenchers and the collision frequency between molecules. At the same time, this process is accompanied by the decay of the luminescence lifetime [45].
To study the quenching processes of Ir1–Ir3, UV–vis absorption spectra were recorded (Figure 9a). As the concentrations of TNP increase, the absorption peak at 257 nm of Ir1 exhibits a slight shift, and the absorption peak at 278 nm disappears, while Ir2 and Ir3 show similar behaviors (Figures S15a and S16a in Supporting Information). This suggests that static quenching may be involved in the quenching process. To confirm whether dynamic quenching is also present in the quenching process, we further conducted luminescence lifetime measurements (Figure 9b, Figures S15b and S16b in Supporting Information). At a low concentration range (TNP concentrations from 0 to 10 μM), the luminescence lifetimes of the complexes remain essentially unchanged. While in the high concentration range, the luminescence lifetimes of the complexes decrease significantly (Figure S17 in Supporting Information). This suggests that the quenching process for the detection of TNP by Ir1–Ir3 may involve both static quenching and dynamic quenching.
The common TNP detection mechanisms include Förster resonance energy transfer (FRET), photo-induced electron transfer (PET), and the inner-filter effect (IFE) [46]. By plotting the emission spectra of Ir1–Ir3 and UV–vis absorption spectrum of TNP, it can be seen that these two spectra do not overlap (Figure 9c, and Figures S15c and S16c in Supporting Information), which rules out the FRET mechanism. We performed density functional theory calculations on Ir2, which has the lowest detection limit, and the results show that the PET mechanism is present in the detection process (Figure S18 in Supporting Information). In addition, the excitation spectra of Ir1–Ir3 and the UV–vis absorption spectrum of TNP were also plotted (Figure 9d, and Figures S15d and S16d in Supporting Information). The excitation spectra of Ir1–Ir3 show partial overlap with the absorption spectrum of TNP, suggesting that there may be IFE in the detection process. In addition, the quenching rates of Ir1–Ir3 were tested at different excitation wavelengths to determine the effect of IFE on quenching (Figure S19 in Supporting Information). The results show that during the quenching process, the influence of IFE on the quenching is much smaller than that of PET [47]. Therefore, it can be deduced that the detection mechanism may be the result of the combined effects of PET and IFE. At the same time, the 1H NMR spectra of Ir1–Ir3 and TNP before and after mixing were tested and demonstrated that the addition of TNP does not lead to decomposition of Ir1–Ir3 (Figures S20–S22 in Supporting Information).

4. Conclusions

In this work, three fluorophenyl-substituted cyclometalated Ir(III) complexes have been synthesized by altering the position of the fluorine atom. The results show that all the complexes possess obvious AIPE properties and exhibit high stability, high selectivity, and excellent anti-interference capability for TNP detection in aqueous media. The KSV for Ir1–Ir3 are 2.7 × 104 M−1, 3.3 × 104 M−1, and 2.3 × 104 M−1, respectively. Their LODs are 124 nM, 101 nM, and 127 nM, respectively. Ir2, with a fluorine atom at the meta position, has the highest KSV and the lowest LOD. Their quenching processes include both a dynamic quenching process and static quenching process, and the quenching mechanism may be attributed to the combination of PET and IFE. This study has enriched the development and application of Ir(III) complexes as luminescent probes for the detection of TNP.

Supplementary Materials

The following supporting information can be downloaded at: https://www.mdpi.com/article/10.3390/chemosensors13080315/s1, Figure S1: Synthesis routes of ligands L1–L3. Figure S2: The 1H NMR spectrum of Ir1 in DMSO-d6. Figure S3: The high-resolution mass spectrum of Ir1. Figure S4: The 13C NMR spectrum of Ir1 in DMSO-d6. Figure S5: The 19F NMR spectrum of Ir1 in DMSO-d6. Figure S6: The 1H NMR spectrum of Ir2 in DMSO-d6. Figure S7: The high-resolution mass spectrum of Ir2. Figure S8: The 13C NMR spectrum of Ir2 in DMSO-d6. Figure S9: The 19F NMR spectrum of Ir2 in DMSO-d6. Figure S10: The 1H NMR spectrum of Ir3 in DMSO-d6. Figure S11: The high-resolution mass spectrum of Ir3. Figure S12: The 13C NMR spectrum of Ir3 in DMSO-d6. Figure S13: The 19F NMR spectrum of Ir3 in DMSO-d6. Table S1: Photophysical properties of Ir1–Ir3. Figure S14: DLS analysis of (a) Ir1, (b) Ir2, and (c) Ir3 in CH3CN/H2O mixtures (Ir1: fw = 60%, Ir2: fw = 70%, Ir3: fw = 70%). Table S2: Some reported complexes for the detection of TNP. Figure S15: (a) The UV–vis absorption spectra of Ir2 upon the addition of TNP with different concentrations; (b) The changes in luminescence lifetime of Ir2 upon the addition of TNP with different concentrations; (c) The normalized UV–vis absorption spectrum of TNP (red line) and the normalized emission spectrum of Ir2 (blue line); (d) The normalized UV–vis absorption spectrum of TNP (red line) and the normalized excitation spectrum of Ir2 (blue line). Figure S16: (a) The UV–vis absorption spectra of Ir3 upon the addition of TNP with different concentrations; (b) The changes in luminescence lifetime of Ir3 upon the addition of TNP with different concentrations; (c) The normalized UV–vis absorption spectrum of TNP (red line) and the normalized emission spectrum of Ir3 (blue line); (d) The normalized UV–vis absorption spectrum of TNP (red line) and the normalized excitation spectrum of Ir3 (blue line). Figure S17: Lifetimes of (a) Ir1 (fw = 60%), (b) Ir2 (fw = 70%), and (c) Ir3 (fw = 70%) in CH3CN/H2O after the addition of TNP with different concentrations. Insert: Lifetimes in the low concentration range (0–10 μM). Figure S18: Energy level diagrams of Ir2 and TNP obtained from theoretical calculations. Figure S19: The quenching rates of (a) Ir1 (fw = 60%), (b) Ir2 (fw = 70%), and (c) Ir3 (fw = 70%) at different excitation wavelengths (310–440 nm). Figure S20: The 1H NMR spectra of Ir1, TNP, and Ir1 + TNP in DMSO-d6. Figure S21: The 1H NMR spectra of Ir2, TNP, and Ir2 + TNP in DMSO-d6. Figure S22: The 1H NMR spectra of Ir3, TNP, and Ir3 + TNP in DMSO-d6.

Author Contributions

Investigation, J.D., R.C., and X.Y.; data curation, visualization, writing—original draft, J.D., R.C., and C.L.; writing—review and editing, X.Y., X.L., and C.L.; funding acquisition, supervision, C.L. All authors have read and agreed to the published version of the manuscript.

Funding

The authors thank the financial support from the National Natural Science Foundation of China (21978042) and the Fundamental Research Funds for the Central Universities (DUT22LAB610).

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

Data are contained within the article.

Conflicts of Interest

The authors declare no conflicts of interest.

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Chemosensors 13 00315 sch001
Scheme 1. Structures and the synthetic routes of Ir1–Ir3. (red markers indicate the different substitution positions of the F atoms).
Scheme 1. Structures and the synthetic routes of Ir1–Ir3. (red markers indicate the different substitution positions of the F atoms).
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Figure 1. (a) The UV–vis absorption spectra and (b) the normalized emission spectra of Ir1–Ir3 in CH3CN (excitation wavelength: 400 nm, c = 10 μM).
Figure 1. (a) The UV–vis absorption spectra and (b) the normalized emission spectra of Ir1–Ir3 in CH3CN (excitation wavelength: 400 nm, c = 10 μM).
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Figure 2. The emission spectra of (a) Ir1, (b) Ir2, and (c) Ir3 in CH3CN/H2O mixtures with varying water contents and (d) the relative intensities I/I0 of Ir1–Ir3. I represents the emission intensities at the maximum emission wavelength in different water contents (Ir1: 574 nm; Ir2: 573 nm; Ir3: 578 nm), while I0 represents the emission intensities at the maximum emission wavelength in CH3CN (excitation wavelength: 400 nm, c = 10 μM).
Figure 2. The emission spectra of (a) Ir1, (b) Ir2, and (c) Ir3 in CH3CN/H2O mixtures with varying water contents and (d) the relative intensities I/I0 of Ir1–Ir3. I represents the emission intensities at the maximum emission wavelength in different water contents (Ir1: 574 nm; Ir2: 573 nm; Ir3: 578 nm), while I0 represents the emission intensities at the maximum emission wavelength in CH3CN (excitation wavelength: 400 nm, c = 10 μM).
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Figure 3. The emission spectra of (a) Ir1 (fw = 60%), (b) Ir2 (fw = 70%), and (c) Ir3 (fw = 70%) in volumetric flasks after being left for different durations, as well as the emission spectra of 11 blank suspension samples for (d) Ir1, (e) Ir2, and (f) Ir3 after reaching equilibrium at 8 h, 7 h, and 4 h, respectively (excitation wavelength: 400 nm, c = 10 μM).
Figure 3. The emission spectra of (a) Ir1 (fw = 60%), (b) Ir2 (fw = 70%), and (c) Ir3 (fw = 70%) in volumetric flasks after being left for different durations, as well as the emission spectra of 11 blank suspension samples for (d) Ir1, (e) Ir2, and (f) Ir3 after reaching equilibrium at 8 h, 7 h, and 4 h, respectively (excitation wavelength: 400 nm, c = 10 μM).
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Figure 4. The Stern–Volmer curves of (a) Ir1 (fw = 60%), (b) Ir2 (fw = 70%), and (c) Ir3 (fw = 70%) for the detection of TNP. Inset: The emission spectra of the complexes in the presence of TNP at different concentrations (top left) and the linear portion of the Stern–Volmer curve (bottom right).
Figure 4. The Stern–Volmer curves of (a) Ir1 (fw = 60%), (b) Ir2 (fw = 70%), and (c) Ir3 (fw = 70%) for the detection of TNP. Inset: The emission spectra of the complexes in the presence of TNP at different concentrations (top left) and the linear portion of the Stern–Volmer curve (bottom right).
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Figure 5. The emission intensity versus TNP concentration relationships for (a) Ir1 (fw = 60%), (b) Ir2 (fw = 70%), and (c) Ir3 (fw = 70%) (excitation wavelength: 400 nm, c = 10 μM).
Figure 5. The emission intensity versus TNP concentration relationships for (a) Ir1 (fw = 60%), (b) Ir2 (fw = 70%), and (c) Ir3 (fw = 70%) (excitation wavelength: 400 nm, c = 10 μM).
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Figure 6. The emission spectra of (a) Ir1 (fw = 60%), (b) Ir2 (fw = 70%), and (c) Ir3 (fw = 70%) after the addition of different analytes (20 equiv.) and the quenching rates of different analytes on (d) Ir1, (e) Ir2, and (f) Ir3 (excitation wavelength: 400 nm, c = 10 μM, CH3CN/H2O).
Figure 6. The emission spectra of (a) Ir1 (fw = 60%), (b) Ir2 (fw = 70%), and (c) Ir3 (fw = 70%) after the addition of different analytes (20 equiv.) and the quenching rates of different analytes on (d) Ir1, (e) Ir2, and (f) Ir3 (excitation wavelength: 400 nm, c = 10 μM, CH3CN/H2O).
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Figure 7. The emission spectra of (a) Ir1 (fw = 60%), (b) Ir2 (fw = 70%), and (c) Ir3 (fw = 70%) after the addition of different ionic compounds (20 equiv.) and the quenching rates of different ionic compounds on (d) Ir1, (e) Ir2, and (f) Ir3 (Excitation wavelength: 400 nm, c = 10 μM, CH3CN/H2O).
Figure 7. The emission spectra of (a) Ir1 (fw = 60%), (b) Ir2 (fw = 70%), and (c) Ir3 (fw = 70%) after the addition of different ionic compounds (20 equiv.) and the quenching rates of different ionic compounds on (d) Ir1, (e) Ir2, and (f) Ir3 (Excitation wavelength: 400 nm, c = 10 μM, CH3CN/H2O).
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Figure 8. The emission spectra of (a) Ir1 (fw = 60%), (b) Ir2 (fw = 70%), and (c) Ir3 (fw = 70%) in different water samples and the quenching rates of (d) Ir1, (e) Ir2, and (f) Ir3 in different water samples (excitation wavelength: 400 nm, c = 10 μM, CH3CN/H2O).
Figure 8. The emission spectra of (a) Ir1 (fw = 60%), (b) Ir2 (fw = 70%), and (c) Ir3 (fw = 70%) in different water samples and the quenching rates of (d) Ir1, (e) Ir2, and (f) Ir3 in different water samples (excitation wavelength: 400 nm, c = 10 μM, CH3CN/H2O).
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Figure 9. (a) The UV–vis absorption spectra of Ir1 upon the addition of TNP with different concentrations; (b) the changes in luminescence lifetime of Ir1 upon the addition of TNP with different concentrations; (c) the normalized UV–vis absorption spectrum of TNP (red line) and the normalized emission spectrum of Ir1 (blue line); (d) the normalized UV–vis absorption spectrum of TNP (red line) and the normalized excitation spectrum of Ir1 (blue line).
Figure 9. (a) The UV–vis absorption spectra of Ir1 upon the addition of TNP with different concentrations; (b) the changes in luminescence lifetime of Ir1 upon the addition of TNP with different concentrations; (c) the normalized UV–vis absorption spectrum of TNP (red line) and the normalized emission spectrum of Ir1 (blue line); (d) the normalized UV–vis absorption spectrum of TNP (red line) and the normalized excitation spectrum of Ir1 (blue line).
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Table 1. The standard deviations and emission intensities of Ir1–Ir3 at 574 nm, 573 nm, and 578 nm, respectively (Ir1: fw = 60%, Ir2: fw = 70%, Ir3: fw = 70%; excitation wavelength: 400 nm, c = 10 μM).
Table 1. The standard deviations and emission intensities of Ir1–Ir3 at 574 nm, 573 nm, and 578 nm, respectively (Ir1: fw = 60%, Ir2: fw = 70%, Ir3: fw = 70%; excitation wavelength: 400 nm, c = 10 μM).
ComplexIr1Ir2Ir3
λ/nm574573578
X1452.1473.1477.0
X2452.4473.5476.6
X3452.4474.6476.7
X4451.9473.6476.4
X5451.2474.4476.8
X6451.4473.9476.7
X7451.3473.4477.0
X8451.2473.2477.6
X9452.1473.9477.5
X10451.9474.0477.4
X11452.3473.5477.8
σ0.45580.45180.4400
Xi (i = 1, 2, 3...., 11) stands for the emission intensity of each sample, i stands for the number of the sample, and σ is the standard deviation.
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Du, J.; Chen, R.; Yang, X.; Li, X.; Liu, C. AIPE-Active Fluorophenyl-Substituted Ir(III) Complexes for Detecting Trinitrophenols in Aqueous Media. Chemosensors 2025, 13, 315. https://doi.org/10.3390/chemosensors13080315

AMA Style

Du J, Chen R, Yang X, Li X, Liu C. AIPE-Active Fluorophenyl-Substituted Ir(III) Complexes for Detecting Trinitrophenols in Aqueous Media. Chemosensors. 2025; 13(8):315. https://doi.org/10.3390/chemosensors13080315

Chicago/Turabian Style

Du, Jiahao, Ruimin Chen, Xiaoran Yang, Xiaona Li, and Chun Liu. 2025. "AIPE-Active Fluorophenyl-Substituted Ir(III) Complexes for Detecting Trinitrophenols in Aqueous Media" Chemosensors 13, no. 8: 315. https://doi.org/10.3390/chemosensors13080315

APA Style

Du, J., Chen, R., Yang, X., Li, X., & Liu, C. (2025). AIPE-Active Fluorophenyl-Substituted Ir(III) Complexes for Detecting Trinitrophenols in Aqueous Media. Chemosensors, 13(8), 315. https://doi.org/10.3390/chemosensors13080315

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