Skip to main content
Log in

A white-light-emitting sensor array based on cucurbit[8]uril for quantitative detection of multicomponent nitroaniline isomers

  • Original Paper
  • Published:
Microchimica Acta Aims and scope Submit manuscript

Abstract

A white-light-emitting supramolecular complex through supramolecular interactions has been assembled; the white luminescent supramolecular complex exhibits two emission spectra. Based on this, a dual-channel white-light array sensor was constructed. The results show that it can quickly identify and detect nitroaniline isomer pollutants (p-nitroaniline, m-nitroaniline, o-nitroaniline). When these three nitroaniline isomers were added to the supramolecular white-light array sensor, the fluorescence intensity of the white-light complex decreased to varying degrees. Linear discriminant analysis (LDA) showed that the supramolecular white-light array sensor could recognize and distinguish three nitroaniline isomers and could classify mixtures containing different concentrations. Factor 1 of the array had a good linear relationship with the concentration of pollutants, and the detection limit (LOD) was as low as 0.7 μM. The method has good reproducibility and stability. In addition, it can also qualitatively detect the nitroaniline isomers in river water and contaminated rice seedling extract. It provides an ideal platform for constructing multiresponse sensors.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

Data Availability

The data that supports the findings of this study are available in the supplementary material of this article. Data available on request.

References

  1. Tong Y-J, Yu L-D, Huang Y-J, Li Y-T, Li N, Fu Q, Ye Y-X, Zhu F, Pawliszyn J, Xu J-Q, Ouyang G-F (2022) High-quality full-color carbon quantum dots synthesized under an unprecedentedly mild condition. IScience 25:104421

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Tong Y-J, Yu L-D, Li N, Shen M-H, Peng X-R, Yang H-S, Ye Y-X, Zhu F, Pawliszyn J, Xu J-Q, Ouyang G-F (2022) Novel lanthanide nanoparticle frameworks for highly efficient photoluminescence and hypersensitive detection. Chem Sci 13:13948–13955

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Calabretta M-M, Lopreside A, Montali L, Zangheri M, Evangelisti L, D’Elia M, Michelini E (2022) Portable light detectors for bioluminescence biosensing applications: a comprehensive review from the analytical chemist’s perspective. Anal Chim Acta 1200:339583

    Article  CAS  PubMed  Google Scholar 

  4. Arabi M, Ostovan A, Wang Y-Q, Mei R-C, Fu L-W, Li J-H, Wang X-Y, Chen L-X (2022) Chiral molecular imprinting-based SERS detection strategy for absolute enantiomeric discrimination. Nat Commun 13:5757

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Arabi M, Chen L-X (2022) Technical challenges of molecular-imprinting-based optical sensors for environmental pollutants. Langmuir 38:5963–5967

    Article  CAS  PubMed  Google Scholar 

  6. Ostovan A, Arabi M, Wang Y-Q, Li J-H, Li B-W, Wang X-Y, Chen L-X (2022) Greenificated molecularly imprinted materials for advanced applications. Adv Mater 34:2203154

    Article  CAS  Google Scholar 

  7. Cong H, Ni X-L, Xiao X, Huang Y, Zhu Q-J, Xue S-F, Tao Z, Lindoy L-F, Wei G (2016) Synthesis and separation of cucurbit[n]urils and their derivatives. Org Biomol Chem 14:4335–4364

    Article  CAS  PubMed  Google Scholar 

  8. Gao C, Cheng Q, Li J-Y, Chen J, Wang Q-F, Wei J-W, Huang Q-X, Lee S-M-Y, Gu D-Y, Wang R-B (2021) Supramolecular macrophage-liposome marriage for cell-hitchhiking delivery and immunotherapy of acute pneumonia and melanoma. Adv Funct Mater 31:2102440

    Article  CAS  Google Scholar 

  9. Chen J, Li S-K, Wang Z-Y, Pan Y-T, Wei J-W, Lu S-Y, Zhang Q-W, Wang L-H, Wang R-B (2021) Synthesis of an AIEgen functionalized cucurbit[7]uril for subcellular bioimaging and synergistic photodynamic therapy and supramolecular chemotherapy. Chem Sci 12:7727–7734

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Dsouza R-N, Pischel U, Nau W-M (2011) Fluorescent dyes and their supramolecular host/guest complexes with macrocycles in aqueous solution. Chem Rev 111:7941–7980

    Article  CAS  PubMed  Google Scholar 

  11. Ndendjio SAZ, Isaacs L (2019) Molecular recognition properties of acyclic cucurbiturils toward amino acids, peptides, and a protein. Supramol Chem 31:432–441

    Article  Google Scholar 

  12. Tang Q, Wang C-H, Xi Y-Y, Huang Y, Tao Z (2019) Host-guest complexes of L-borneol with cucurbituril and cyclodextrin and its potential use in analysis of drugs. ChemistrySelect 4:6924–6929

    Article  CAS  Google Scholar 

  13. Wu H, Zhao J, Yang X-N, Yang D, Chen L-X, Redshaw C, Yang L-G, Tao Z, Xiao X (2022) A cucurbit[8]uril-based probe for the detection of the pesticide tricyclazole. Dyes Pigm 199:110076

    Article  CAS  Google Scholar 

  14. Li Z, Askim J-R, Suslick K-S (2019) The optoelectronic nose: colorimetric and fluorometric sensor arrays. Chem Rev 119:231–292

    Article  CAS  PubMed  Google Scholar 

  15. Sun X-C, Wang Y, Lei Y (2015) Fluorescence based explosive detection: from mechanisms to sensory materials. Chem Soc Rev 44:8019–8061

    Article  CAS  PubMed  Google Scholar 

  16. Smith D-G, Topolnicki I-L, Zwicker V-E, Jolliffe K-A, New E-J (2017) Fluorescent sensing arrays for cations and anions. Analyst 142:3549–3563

    Article  CAS  PubMed  Google Scholar 

  17. Wu L, Qu X-G (2015) Cancer biomarker detection: recent achievements and challenges. Chem Soc Rev 44:2963–2997

    Article  CAS  PubMed  Google Scholar 

  18. Sun Y, Lu F-N, Yang H-W, Ding C-F, Yuan Z-Q, Lu C (2019) Fluorescent sensor array for separation-free dopamine analogue discrimination via polyethyleneimine-mediated self-polymerization reaction. Nanoscale 11:12889

    Article  CAS  PubMed  Google Scholar 

  19. Yang H-W, Lu F-N, Sun Y, Yuan Z-Q, Lu C (2018) Fluorescent gold nanocluster-based sensor array for nitrophenol isomer discrimination via an integration of host-guest interaction and inner filter effect. Anal Chem 90:12846

    Article  CAS  PubMed  Google Scholar 

  20. Ni X-L, Chen S-Y, Yang Y-P, Tao Z (2016) Facile cucurbit[8]uril-based supramolecular approach to fabricate tunable luminescent materials in aqueous solution. J Am Chem Soc 138:6177–6183

    Article  CAS  PubMed  Google Scholar 

  21. Li X-S, Li Y-F, Wu J-R, Lou X-Y, Han J-Y, Qin J-C, Yang Y-W (2020) A color-tunable fluorescent pillararene coordination polymer for efficient pollutant detection. J Mater Chem A 8:3651–3657

    Article  CAS  Google Scholar 

  22. Sun M, Li Y, Zhao L, Zhang X, Zhang C, Jin X, Shan D, Li G (2021) Luminescence-color-changing sensing toward melamine based on a white-light-emitting film. ACS Appl Polym Mater 3:2998–3008

    Article  CAS  Google Scholar 

  23. Song N, Lou X-Y, Yu H, Weiss P-S, Tang B-Z, Yang Y-W (2020) Pillar[5]arene-based tunable luminescent materials via supramolecular assembly-induced Förster resonance energy transfer enhancement. Mater Chem Front 4:950–956

    Article  Google Scholar 

  24. Li D, Wang J, Ma X (2018) White-light-emitting materials constructed from supramolecular approaches. Adv Opt Mater 6:1800273

    Article  Google Scholar 

  25. Xia Y, Chen S, Ni X-L (2018) White light emission from cucurbituril-based host–guest interaction in the solid state: new function of the macrocyclic host. ACS Appl Mater Interfaces 10:13048–13052

    Article  CAS  PubMed  Google Scholar 

  26. Kim J, Jung I-S, Kim S-Y, Lee E, Kang J-K, Sakamoto S, Yamaguchi K, Kim K (2000) New cucurbituril homologues: syntheses, isolation, characterization, and X-ray crystal structures of cucurbit[n]uril (n=5, 7, and 8). J Am Chem Soc 122:540–541

    Article  CAS  Google Scholar 

  27. Zhang T-T, Yang X-N, Hu J-H, Luo Y, Liu H-J, Tao Z, Xiao X, Redshaw C (2023) New dual-mode orthogonal tunable fluorescence systems based on cucurbit[8]uril: white light, 3D printing, and anti-counterfeit applications. Chem Eng J 452:138960

    Article  CAS  Google Scholar 

  28. Barooah N, Khurana R, Mohanty J, Bhasikuttan A-C (2017) Modulation of protolytic equilibrium of bichromophoric coumarin-30 dye with cucurbit[8]uril encapsulation. Chem Sel 24:7387–7393

    Google Scholar 

  29. Cao Y-J, Wang S, Wu W, Peng H, Yu Y, Zhu D-B (2019) Cucurbit[6]uril modified CdTe quantum dots fluorescent probe and its selective analysis of p-nitroaniline in environmental samples. Talanta 199:667–673

    Article  CAS  PubMed  Google Scholar 

  30. Hong H-T, Wu N, Han M-X, Guo Z-Y, Zhan H-B, Dub S-W, Chen B-L (2021) An anthracene based conjugated triazine framework as a luminescent probe for selective sensing of p-nitroaniline and Fe(III) ions. Mater Chem Front 5:6568

    Article  CAS  Google Scholar 

  31. Bhuvaneswari C, Palpandi K, Raman N, Babu S-G (2022) Sustainable architecting of Co2SnO4/CE-BN-based electrochemical platform for highly selective and ultrasensitive detection of 2-nitroaniline in life samples. Microchim Acta 189:390

    Article  CAS  Google Scholar 

  32. Li H-L, Cao J-Y, Yu Z-D, Yang G, Xue Z-M, Wang C-Z, Zhao W-X, Zhao Y, Redshaw C, Yamato T (2023) A substituent-dependent deep-blue pyrene-based chemosensor for trace nitroaniline sensing. Mater Chem Front 7:3365–3372

    Article  CAS  Google Scholar 

Download references

Funding

We thank the National Natural Science Foundation of China (No. 22061009) and the Natural Science Foundation of the Science and Technology Department of Guizhou Province (Grant No. ZK-2021–024) for financial support.

Author information

Authors and Affiliations

Authors

Contributions

Shu-Zhen Huang: conceptualization, formal analysis, investigation, methodology, visualization, validation, writing–original draft. Kai-Ni Wei: conceptualization, formal analysis, visualization. Ru-Pei Yang: performing cultivation and extraction of rice seedlings. Hong-Ling Yi: performing the anti-interference experiment. Qing Tang: formal analysis, resources, data curation, methodology. Zhu Tao: term, conceptualization, methodology, supervision, project administration. Ying Huang: term, conceptualization, methodology, supervision, funding acquisition, project administration, writing–review and editing.

Corresponding author

Correspondence to Ying Huang.

Ethics declarations

Conflict of interest

The authors declare no competing interests.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 15.8 MB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Huang, SZ., Wei, KN., Yang, RP. et al. A white-light-emitting sensor array based on cucurbit[8]uril for quantitative detection of multicomponent nitroaniline isomers. Microchim Acta 190, 460 (2023). https://doi.org/10.1007/s00604-023-06040-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s00604-023-06040-2

Keywords

Navigation