Skip to main content
Log in

A Fluorescent Turn-On Sensor Toward Multiple Heavy Metal Ions Based on Meso-anisole Modified BODIPY Scaffold

  • Research
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

A fluorescent turn-on sensor (BOPA) was configured by anchoring bis(pyridin-2-ylmethyl)-amine (DPA) unit to the BODIPY scaffold. It exhibits highly sensitivity and selectivity towards Pb2+, Ba2+, Cr3+, Cd2+, Hg2+, Zn2+ against the competent metal ions. Job’s plot analysis supports the 1:1 stoichiometry of BOPA and metal ions. And linear relationship between fluorescence intensity and concentration of Zn2+ (representative metal ion) was observed over the range 0 ~ 20 μM Zn2+. The limit detection of BOPA in recognition of Pb2+, Ba2+, Cr3+, Cd2+, Hg2+, Zn2+ was ranged from 15.99 to 43.57 nM. Photo induced transfer (PET) in the excited state of BOPA determines the emission “off/on”. Coordination of metal ions by DPA significantly weakened the electron-donating ability of nitrogen atom and inhibits the PET, recovering emission of BODIPY. In addition, the attachment of anisole at meso-position of BODIPY finely modulated the recognition of metal ions category.

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

Similar content being viewed by others

Data Availability

All data generated or analysed during this study are included in this published article.

References

  1. Baroncini M, Silvi S, Credi A (2020) Photo- and redox-driven artificial molecular motors. Chem Rev 120:200–268. https://doi.org/10.1021/acs.chemrev.9b00291

    Article  CAS  PubMed  Google Scholar 

  2. Li X, Han Y, Sun S, Shan D, Ma X, He G, Mergu N, Park JS, Kim CH, Son YA (2020) A diaminomaleonitrile-appended BODIPY chemosensor for the selective detection of Cu2+ via oxidative cyclization and imaging in SiHa cells and zebrafish. Spectrochim Acta Part A 233:118179. https://doi.org/10.1016/j.saa.2020.118179

    Article  CAS  Google Scholar 

  3. Cheng H, Qian Y (2015) Intramolecular fluorescence resonance energy transfer in a novel PDI–BODIPY dendritic structure: Synthesis, Hg2+ sensor and living cell imaging. Sens Actuators B Chem 219:57–64. https://doi.org/10.1016/j.snb.2015.04.086

    Article  CAS  Google Scholar 

  4. Karmakar S, Mardanya S, Maity D, Baitalik S (2016) Polypyridyl-imidazole based Os(II) complex as optical chemosensorfor anions and cations and multi-readout molecular logic gates and memory device: experimental and DFT/TDDFT study. Sens Actuators B Chem 226:388–402. https://doi.org/10.1016/j.snb.2015.11.104

    Article  Google Scholar 

  5. Langton MJ, Beer PD (2014) Rotaxane and catenane host structures for sensing charged guest species. Acc Chem Res 47:1935–1949. https://doi.org/10.1021/ar500012a

    Article  CAS  PubMed  Google Scholar 

  6. Jongkhumkrong J, Thaveesangsakulthai I, Sukbangnop W et al (2022) Helicene-hydrazide encapsulated ethyl cellulose as a potential fluorescence sensor for highly specific detection of nonanal in aqueous solutions and a proof-of-concept clinical study in lung fluid. ACS Appl Mater Interfaces (in press). https://doi.org/10.1021/acsami.2c11064) https://doi.org/10.1021/acsami.2c11064

  7. Dias GG, Rodrigues MO, Paz ERS et al (2022) Aryl-phenanthro[9,10-d]imidazole: a versatile scaffold for the design of optical-based sensors. Acs Sens 10: 2565-2919. https://doi.org/10.1021/acssensors.2c01687

  8. Guo Z, Shin I, Yoon J (2012) Recognition and sensing of various species using boronic acid derivatives. Chem Commun 48:5956–5967. https://doi.org/10.1039/C2CC31985C

    Article  CAS  Google Scholar 

  9. Yuan L, Su Y, Cong H, Yu B, Shen Y (2022) Application of multifunctional small molecule fluorescent probe BODIPY in life science. Dye Pigm 208:110851. https://doi.org/10.1016/j.dyepig.2022.110851

    Article  CAS  Google Scholar 

  10. Guo Z, Par S, Yoon J, Shin I (2014) Recent progress in the development of near-infrared fluorescent probes for bioimaging applications. Chem Soc Rev 43:16–29. https://doi.org/10.1039/C3CS60271K

    Article  PubMed  Google Scholar 

  11. Zhu M, Shi C, Xu X, Guo Z, Zhu W (2016) Near-infrared cyanine-based sensor for Fe3+ with high sensitivity: its intracellular imaging application in colorectal cancer cells. RSC Adv 6:100759–100764. https://doi.org/10.1039/C6RA22966B

    Article  CAS  Google Scholar 

  12. Sil A, Islam SN, Patra SK (2018) Terpyridyl appended poly(metaphenylene-alt-fluorene) π-conjugated fluorescent polymers: highly selective and sensitive turn off probes for the detection of Cu2+. Sens Act B Chem 254:618–628. https://doi.org/10.1016/j.snb.2017.07.067

    Article  CAS  Google Scholar 

  13. Barnham KJ, Masters CL, Bush AI (2004) Bush, Neurodegenerative diseases and oxidative stress. Nat Rev Drug Discov 3:205–214. https://www.nature.com/articles/nrd1330

  14. Li X, Ji G, Son YA (2016) Tunable emission of hydrazine-containing bipyrrole fluoring-boron complexes by linear extension. Dyes Pigm 124:232–240. https://doi.org/10.1016/j.dyepig.2015.09.022

    Article  CAS  Google Scholar 

  15. Li X, Guo X, Chen Y, Cui T, Xing L (2021) Double 3-ethyl-2,4-diemthylpyrrole configured fluorescent dye with fluorine-boron as the bridge. J Fluoresc 31:1797–1803. https://doi.org/10.1007/s10895-021-02819-9

    Article  CAS  PubMed  Google Scholar 

  16. Loudet A, Burgess K (2007) BODIPY dyes and their derivatives: synthesis and spectroscopic properties. Chem Rev 107:4891–4932. https://doi.org/10.1021/cr078381n

    Article  CAS  PubMed  Google Scholar 

  17. Li X, Han Y, Kim MJ, Son YA (2018) A BODIPY-based highly emissive dye with thiophene-based branch harvesting the light. Mol Cryst Liq Cryst 662:157–164. https://doi.org/10.1080/15421406.2018.1467613

    Article  CAS  Google Scholar 

  18. Boodts S, Fron E, Hofkens H, Dehaen W (2018) The BOPHY fluorphore with double boron chelation: synthesis and spectroscopy. Coordin Chem Rev 371:1–10. https://doi.org/10.1016/j.ccr.2018.05.011

    Article  CAS  Google Scholar 

  19. Patalag LJ, Ulrichs JA, Jones PG, Werz DB (2017) Decorated BODIPY fluorophores and thiol-reactive fluorescence probes by an aldol addition. Org Lett 19:2090–2093. https://doi.org/10.1021/acs.orglett.7b00693

    Article  CAS  PubMed  Google Scholar 

  20. Hiruta Y, Koiso H, Ozawa H, Sato H, Hamada K, Yabushita S, Citterio D, Suzuki K (2015) Near IR emitting red-shifting ratiometric fluorophores based on borondipyrromethene. Org Lett 17:3022–3025. https://doi.org/10.1021/acs.orglett.5b01299

    Article  CAS  PubMed  Google Scholar 

  21. Li Y, Zhou H, Yin S, Jiang H, Niu N, Huang H, Szhzad SA, Yu C (2016) A BOPHY probe for the fluorescence turn-on detection of Cu2+. Sens Actuators B Chem 235:33–38. https://doi.org/10.1016/j.snb.2016.05.055

    Article  CAS  Google Scholar 

  22. Bastug E, Kursunlu AN, Guler E (2020) A fluorescent clever macrocycle: deca-bodipy bearing a pillar [5]arene and its selective binding of asparagine in half-aqueous medium. J Lumin 225:117343. https://doi.org/10.1016/j.jlumin.2020.117343

    Article  CAS  Google Scholar 

  23. Kursunlu AN, Ozmen M, Guler E (2019) A novel fluorescent chemosensor for cu (II) ion: Click synthesis of dual-bodipy including the triazole groups and bioimaging of yeast cells. J Fluoresc 29:1321–1329. https://doi.org/10.1007/s10895-019-02456-3

    Article  CAS  PubMed  Google Scholar 

  24. Kursunlu AN, Sahin E, Guler E (2016) Cu (II) chemosensor based on a fluorogenic bodipy-salophen combination: sensitivity and selectivity studies. J Fluoresc 26:1997–2004. https://doi.org/10.1007/s10895-016-1893-1

    Article  CAS  PubMed  Google Scholar 

  25. Lin JR, Chu CJ, Venkatesan P, Wu SP (2015) Zinc(II) and pyrophosphate selective fluorescence probe and itsapplication to living cell imaging. Sens Actuators B Chem 207:563–570. https://doi.org/10.1016/j.snb.2014.10.109

    Article  CAS  Google Scholar 

  26. Li X, Tian G, Shao D, Xu Y, Wang Y, Ji G, Ryu J, Son YA (2020) A BODIPY based emission signal turn-on probe toward multiple heavy metals. Mol Cryst Liq Cryst 706:38–46. https://doi.org/10.1080/15421406.2020.1743436

    Article  CAS  Google Scholar 

  27. Li X, Ji G, Jung JM, Son YA (2016) A BODIPY based highly selective fluorescence turn-on sensor toward VIB and IIB metal ions. Mol Cryst Liq Cryst 636:159–167. https://doi.org/10.1080/15421406.2016.1201406

    Article  CAS  Google Scholar 

  28. Atilgan S, Ozdemir T, Akkaya EU (2008) A sensitive and selective ratiometric near IR fluorescent probe for zinc ions based on the distyryl-bodipy fluorophore. Org Lett 10:4065–4067. https://doi.org/10.1021/ol801554t

    Article  CAS  PubMed  Google Scholar 

  29. Kang G, Son H, Lim JM, Kweon HS, Lee IS, Kang D, Jong H (2012) Functionalized Fe O nanoparticles for detecting zinc ions in living cells and their cytotoxicity. Chem Eur J 18:5843–5847. https://doi.org/10.1002/chem.201200294

    Article  CAS  PubMed  Google Scholar 

  30. Zhao C, Zhang Y, Feng P, Cao J (2012) Development of a borondipyrromethene-based Zn2+ fluorescent probe: solvent effects on modulation sensing ability. Dalton T 41:831–838. https://doi.org/10.1039/C1DT10797F

    Article  CAS  Google Scholar 

  31. Wu Y, Peng X, Guo B, Fan J, Zhang Z, Wang J, Cui A, Gao Y (2005) Boron dipyrromethene fluorophore based fluorescence sensor for the selective imaging of Zn(ii) in living cells. Org Biomol Chem 3:1387–1392. https://doi.org/10.1039/B501795E

    Article  CAS  PubMed  Google Scholar 

  32. Raveendran AV, Sankeerthana PA, Jayaraj A, Swamy CA (2022) Recent developments on BODIPY based chemosensors for the detection of group IIB metal ions. Results in Chemistry 4:100297. https://doi.org/10.1016/j.rechem.2022.100297

    Article  CAS  Google Scholar 

  33. Qin W, Dou W, Leen V, Dehaen W, Auweraer MV, Boens N (2016) A ratiometric, fluorescent BODIPY-based probe for transition and heavy metal ions. RSC Adv 6:7806–7816. https://doi.org/10.1039/C5RA23751C

    Article  CAS  Google Scholar 

  34. Song Y, Tao J, Wang Y, Cai Z, Fang X, Wang S, Xu H (2021) A novel dual-responsive fluorescent probe for the detection of copper(II) and nickel(II) based on BODIPY derivatives. Inorg Chim Acta 516:120099. https://doi.org/10.1016/j.ica.2020.120099

    Article  CAS  Google Scholar 

  35. Zhu S, Zhang J, Janjanam J, Vegesna G, Luo FT, Tiwari A, Liu H (2013) Highly water-soluble BODIPY-based fluorescent probes for sensitive fluorescent sensing of zinc(ii). J Mater Chem B 1:1722–1728. https://doi.org/10.1039/C3TB00249G

    Article  CAS  PubMed  Google Scholar 

  36. Jia X, Yu X, Zhang G, Liu W, Qin W (2013) Preparation of a fluorescent sensor based on BODIPY-functionalized hydroxyapatite nanoparticles and spectroscopic study of the Cd2+ and Zn2+ complex formation. J Coord Chem 66:662–670

    Article  CAS  Google Scholar 

  37. Jiao L, Yu C, Li J, Wang Z, Wu M, Hao E (2009) β-Formyl-BODIPYs from the vilsmeier-haack reaction. J Org Chem 74:7525–7528. https://doi.org/10.1021/jo901407h

    Article  CAS  PubMed  Google Scholar 

  38. Li X, Liao M, Sun J, Heo G, Son YA (2019) Thiophene modulated BODIPY dye as a light harvester. Mol Cryst Liq Cryst 679:127–136. https://doi.org/10.1080/15421406.2019.1597557

    Article  CAS  Google Scholar 

  39. Benesi HA, Hildebrand JH (1949) A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J Am Chem Soc 71:2703–2707. https://doi.org/10.1021/ja01176a030

    Article  CAS  Google Scholar 

Download references

Funding

This work was supported by the National Natural Science Foundation of China (grant no. 21772034) We also thank the financial support from Henan Key Laboratory of Organic Functional Molecules and Drug Innovation.

Author information

Authors and Affiliations

Authors

Contributions

All the authors (Guangqian Ji, Fangfang Li, and Xiaochuan Li) made substantial contribution while preparing the manuscript. All authors contributed to the study conception and design. Material preparation, data collection and analysis were performed by Guangqian Ji, and Fangfang Li. The first draft of the manuscript was written by Xiaochuan Li. Guangqian Ji prepared Figs. 15 and Fangfang Li prepared Scheme 13. All authors read and approved the final manuscript.

Corresponding author

Correspondence to Xiaochuan Li.

Ethics declarations

Ethical Approval

Not applicable.

Consent to Participate

Not applicable.

Consent for Publication

Not applicable.

Conflict of Interest

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

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 (DOC 3329 KB)

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

Li, X., Li, F. & Ji, G. A Fluorescent Turn-On Sensor Toward Multiple Heavy Metal Ions Based on Meso-anisole Modified BODIPY Scaffold. J Fluoresc 33, 631–637 (2023). https://doi.org/10.1007/s10895-022-03110-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-022-03110-1

Keywords

Navigation