A DIE responsive fluorescent probe for phthalate and its application in test paper and hydrogel detection platforms
[Display omitted] •An amphiphilic BODIPY probe named BOD-Bea for the detection of DPP was reported.•Selective fluorescence turn-on recognition of DPP was presented.•The mechanism by which the probe recognized DPP was revealed.•Two instrument-free solid sensors based on BOD-Bea are fabricated to rapi...
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| Veröffentlicht in: | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Jg. 341; S. 126403 |
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| Format: | Journal Article |
| Sprache: | Englisch |
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England
Elsevier B.V
15.11.2025
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| ISSN: | 1386-1425, 1873-3557, 1873-3557 |
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| Abstract | [Display omitted]
•An amphiphilic BODIPY probe named BOD-Bea for the detection of DPP was reported.•Selective fluorescence turn-on recognition of DPP was presented.•The mechanism by which the probe recognized DPP was revealed.•Two instrument-free solid sensors based on BOD-Bea are fabricated to rapidly and sensitively monitor DPP.
Phthalates, classified as priority environmental contaminants, have driven intensive methodological development for environmental monitoring due to their well-documented endocrine-disrupting effects. Despite these imperatives, the design of optical probes for phthalate detection remains challenging probably due to the lack of suitable functional groups/sensing mode. Additionally, the reported probes were applied in the form of suspensions, resulting in difficulties in separation and recovery during the practical applications. Addressing these limitations, we engineered an amphiphilic BODIPY derivative (BOD-Bea) featuring a bespoke molecular architecture that self-assembles into non-fluorescent aggregates in aqueous media. Upon dipentyl phthalate (DPP) binding, significant fluorescence and absorption enhancements were elicited through the mechanism of disaggregation-induced emission (DIE). From the titration experiments, both the fluorescence emission at 653 nm and absorption at 576 nm demonstrate linear correlations with DPP concentrations in the range of 0–26 μM. The calculated LODs were determined to be 0.11 μM for fluorescence detection and 1.24 μM for absorption measurement. Detailed binding mechanism reveals that the probe achieves specific DPP recognition through synergistic interactions: π–π stacking anchoring the benzene ring moiety and hydrophobic capturing of the alkyl chain. Finally, probe BOD-Bea has been successfully employed to quantify DPP in the real water samples with good recoveries. Meanwhile, two instrument-free solid sensors based on BOD-Bea (i.e., test paper and hydrogel) are fabricated to rapidly and sensitively monitor DPP. This strategy overcomes the disadvantages of complex and costly pre-treatment of traditional methods and provides a molecular design basis for rapid on-site detection. |
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| AbstractList | [Display omitted]
•An amphiphilic BODIPY probe named BOD-Bea for the detection of DPP was reported.•Selective fluorescence turn-on recognition of DPP was presented.•The mechanism by which the probe recognized DPP was revealed.•Two instrument-free solid sensors based on BOD-Bea are fabricated to rapidly and sensitively monitor DPP.
Phthalates, classified as priority environmental contaminants, have driven intensive methodological development for environmental monitoring due to their well-documented endocrine-disrupting effects. Despite these imperatives, the design of optical probes for phthalate detection remains challenging probably due to the lack of suitable functional groups/sensing mode. Additionally, the reported probes were applied in the form of suspensions, resulting in difficulties in separation and recovery during the practical applications. Addressing these limitations, we engineered an amphiphilic BODIPY derivative (BOD-Bea) featuring a bespoke molecular architecture that self-assembles into non-fluorescent aggregates in aqueous media. Upon dipentyl phthalate (DPP) binding, significant fluorescence and absorption enhancements were elicited through the mechanism of disaggregation-induced emission (DIE). From the titration experiments, both the fluorescence emission at 653 nm and absorption at 576 nm demonstrate linear correlations with DPP concentrations in the range of 0–26 μM. The calculated LODs were determined to be 0.11 μM for fluorescence detection and 1.24 μM for absorption measurement. Detailed binding mechanism reveals that the probe achieves specific DPP recognition through synergistic interactions: π–π stacking anchoring the benzene ring moiety and hydrophobic capturing of the alkyl chain. Finally, probe BOD-Bea has been successfully employed to quantify DPP in the real water samples with good recoveries. Meanwhile, two instrument-free solid sensors based on BOD-Bea (i.e., test paper and hydrogel) are fabricated to rapidly and sensitively monitor DPP. This strategy overcomes the disadvantages of complex and costly pre-treatment of traditional methods and provides a molecular design basis for rapid on-site detection. Phthalates, classified as priority environmental contaminants, have driven intensive methodological development for environmental monitoring due to their well-documented endocrine-disrupting effects. Despite these imperatives, the design of optical probes for phthalate detection remains challenging probably due to the lack of suitable functional groups/sensing mode. Additionally, the reported probes were applied in the form of suspensions, resulting in difficulties in separation and recovery during the practical applications. Addressing these limitations, we engineered an amphiphilic BODIPY derivative (BOD-Bea) featuring a bespoke molecular architecture that self-assembles into non-fluorescent aggregates in aqueous media. Upon dipentyl phthalate (DPP) binding, significant fluorescence and absorption enhancements were elicited through the mechanism of disaggregation-induced emission (DIE). From the titration experiments, both the fluorescence emission at 653 nm and absorption at 576 nm demonstrate linear correlations with DPP concentrations in the range of 0-26 μM. The calculated LODs were determined to be 0.11 μM for fluorescence detection and 1.24 μM for absorption measurement. Detailed binding mechanism reveals that the probe achieves specific DPP recognition through synergistic interactions: π-π stacking anchoring the benzene ring moiety and hydrophobic capturing of the alkyl chain. Finally, probe BOD-Bea has been successfully employed to quantify DPP in the real water samples with good recoveries. Meanwhile, two instrument-free solid sensors based on BOD-Bea (i.e., test paper and hydrogel) are fabricated to rapidly and sensitively monitor DPP. This strategy overcomes the disadvantages of complex and costly pre-treatment of traditional methods and provides a molecular design basis for rapid on-site detection.Phthalates, classified as priority environmental contaminants, have driven intensive methodological development for environmental monitoring due to their well-documented endocrine-disrupting effects. Despite these imperatives, the design of optical probes for phthalate detection remains challenging probably due to the lack of suitable functional groups/sensing mode. Additionally, the reported probes were applied in the form of suspensions, resulting in difficulties in separation and recovery during the practical applications. Addressing these limitations, we engineered an amphiphilic BODIPY derivative (BOD-Bea) featuring a bespoke molecular architecture that self-assembles into non-fluorescent aggregates in aqueous media. Upon dipentyl phthalate (DPP) binding, significant fluorescence and absorption enhancements were elicited through the mechanism of disaggregation-induced emission (DIE). From the titration experiments, both the fluorescence emission at 653 nm and absorption at 576 nm demonstrate linear correlations with DPP concentrations in the range of 0-26 μM. The calculated LODs were determined to be 0.11 μM for fluorescence detection and 1.24 μM for absorption measurement. Detailed binding mechanism reveals that the probe achieves specific DPP recognition through synergistic interactions: π-π stacking anchoring the benzene ring moiety and hydrophobic capturing of the alkyl chain. Finally, probe BOD-Bea has been successfully employed to quantify DPP in the real water samples with good recoveries. Meanwhile, two instrument-free solid sensors based on BOD-Bea (i.e., test paper and hydrogel) are fabricated to rapidly and sensitively monitor DPP. This strategy overcomes the disadvantages of complex and costly pre-treatment of traditional methods and provides a molecular design basis for rapid on-site detection. Phthalates, classified as priority environmental contaminants, have driven intensive methodological development for environmental monitoring due to their well-documented endocrine-disrupting effects. Despite these imperatives, the design of optical probes for phthalate detection remains challenging probably due to the lack of suitable functional groups/sensing mode. Additionally, the reported probes were applied in the form of suspensions, resulting in difficulties in separation and recovery during the practical applications. Addressing these limitations, we engineered an amphiphilic BODIPY derivative (BOD-Bea) featuring a bespoke molecular architecture that self-assembles into non-fluorescent aggregates in aqueous media. Upon dipentyl phthalate (DPP) binding, significant fluorescence and absorption enhancements were elicited through the mechanism of disaggregation-induced emission (DIE). From the titration experiments, both the fluorescence emission at 653 nm and absorption at 576 nm demonstrate linear correlations with DPP concentrations in the range of 0-26 μM. The calculated LODs were determined to be 0.11 μM for fluorescence detection and 1.24 μM for absorption measurement. Detailed binding mechanism reveals that the probe achieves specific DPP recognition through synergistic interactions: π-π stacking anchoring the benzene ring moiety and hydrophobic capturing of the alkyl chain. Finally, probe BOD-Bea has been successfully employed to quantify DPP in the real water samples with good recoveries. Meanwhile, two instrument-free solid sensors based on BOD-Bea (i.e., test paper and hydrogel) are fabricated to rapidly and sensitively monitor DPP. This strategy overcomes the disadvantages of complex and costly pre-treatment of traditional methods and provides a molecular design basis for rapid on-site detection. |
| ArticleNumber | 126403 |
| Author | Yu, Xiao-Feng Li, Lu-Yu Li, Ze-Kai Fan, Xu-Bo Shu, Jing Wang, Ming-Qi |
| Author_xml | – sequence: 1 givenname: Lu-Yu surname: Li fullname: Li, Lu-Yu – sequence: 2 givenname: Ze-Kai surname: Li fullname: Li, Ze-Kai – sequence: 3 givenname: Jing surname: Shu fullname: Shu, Jing – sequence: 4 givenname: Xu-Bo surname: Fan fullname: Fan, Xu-Bo – sequence: 5 givenname: Xiao-Feng surname: Yu fullname: Yu, Xiao-Feng – sequence: 6 givenname: Ming-Qi surname: Wang fullname: Wang, Ming-Qi email: wmq3415@163.com |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/40381237$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1016/j.fct.2021.112003 10.1016/j.aca.2023.341828 10.1360/SSC-2022-0080 10.1093/chromsci/bmt070 10.1016/j.foodchem.2020.127359 10.1021/ma902740t 10.1016/j.cclet.2022.07.013 10.1021/jacs.7b08176 10.1038/s41427-021-00318-8 10.1007/s12161-018-01421-3 10.1016/j.saa.2021.119492 10.1021/acsomega.3c02452 10.1016/j.ecoenv.2024.116763 10.1016/j.aca.2022.339460 10.1016/j.foodchem.2023.137260 10.1039/D3TB00268C 10.1039/D0SC06928K 10.1021/ac950944k 10.1016/j.scitotenv.2021.147371 10.1016/j.dyepig.2023.111357 10.1016/j.biortech.2021.126249 10.1021/acs.jpcc.4c04236 10.1016/j.bioorg.2024.107360 10.1016/j.envres.2022.115196 10.1021/es4042034 10.1039/D0NJ02887H 10.1134/S1061934821010056 10.1039/D4NH00186A 10.1016/j.jenvman.2012.05.014 10.1016/j.snb.2020.129396 10.1021/acs.orglett.2c04184 10.1039/C5RA01916H 10.1007/s00204-020-02683-9 |
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| Keywords | Test paper BODIPY Hydrogel-based sensing Phthalates Fluorescent probe |
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•An amphiphilic BODIPY probe named BOD-Bea for the detection of DPP was reported.•Selective fluorescence turn-on recognition of DPP was... Phthalates, classified as priority environmental contaminants, have driven intensive methodological development for environmental monitoring due to their... |
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| SubjectTerms | BODIPY Boron Compounds - chemistry Fluorescent Dyes - chemistry Fluorescent probe Hydrogel-based sensing Hydrogels - analysis Hydrogels - chemistry Limit of Detection Phthalates Phthalic Acids - analysis Spectrometry, Fluorescence - methods Test paper |
| Title | A DIE responsive fluorescent probe for phthalate and its application in test paper and hydrogel detection platforms |
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