Skip to main content
Log in

Visible-light Excited and Highly Photostable Organic Fluorophore with dual-state Emission

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

Abstract

Organic fluorophores with dual-state emission (DSE) are rare or difficult to observe because most of them display either aggregation-induced emission (AIE) or aggregation-caused quenching (ACQ). Amazing works have been accomplished, yet most of the DSE compounds were excited by UV light which limits their wide application in bioimaging. In this work, we achieved a visible-light excited DSE fluorophore and realized its imaging in SKOV-3 cells and zebrafish. The naphtho[2’,3’:4,5]imidazo[1,2-a]pyridine (NIP) core ensures its emission in dilute solution. Meanwhile, the twisted phenyl ring blocks fluorescence quenching induced by the π-π stacking and leads to the emission of the solid. The fluorescence intensity is steady even after 6 h of continuous intense sunlight. More importantly, photostability of NIP in cells is much better than commercial dye (mitochondrial green).

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.

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

Similar content being viewed by others

Data Availability

Supplementary data associated with this article can be found in the online version.

References

  1. Rodríguez-Cortés LA, Navarro-Huerta A, Rodríguez-Molina B (2021) One molecule to light it all: the era of Dual-State Emission. Matter 4:2622–2624. https://doi.org/10.1016/j.matt.2021.06.023

    Article  CAS  Google Scholar 

  2. Belmonte-Vazquez JL, Amador-Sanchez YA, Rodríguez-Cortés LA, Rodríguez-Molina B (2021) Dual-State Emission (DSE) in Organic Fluorophores: design and applications. Chem Mater 33:7160–7184. https://doi.org/10.1021/acs.chemmater.1c02460

    Article  CAS  Google Scholar 

  3. Mei J, Leung NLC, Kwok RTK, Lam JWY, Tang BZ (2015) Aggregation-Induced Emission: together we Shine, United we soar! Chem Rev 115:11718–11940. https://doi.org/10.1021/acs.chemrev.5b00263

    Article  CAS  PubMed  Google Scholar 

  4. Yang Y, Zhao Q, Feng W, Li F (2013) Luminescent chemodosimeters for Bioimaging. Chem Rev 113:192–270. https://doi.org/10.1021/cr2004103

    Article  CAS  PubMed  Google Scholar 

  5. Yuan L, Lin W, Zheng K, He L, Huang W (2013) Far-red to Near Infrared analyte-responsive fluorescent probes based on Organic Fluorophore Platforms for fluorescence imaging. Chem Soc Rev 42:622–661. https://doi.org/10.1039/C2CS35313J

    Article  CAS  PubMed  Google Scholar 

  6. Zhao Z, Zhang H, Lam JWY, Tang BZ (2020) Aggregation-Induced Emission: New Vistas at the aggregate level. Angew Chem Int Ed 59:9888–9907. https://doi.org/10.1002/anie.201916729

    Article  CAS  Google Scholar 

  7. Prusti B, Tripathi S, Sivasakthi P, Samanta PK, Chakravarty M (2023) Solution and solid-state emissive organophosphonates with high-contrast eversible mechanofluorochromism: beyond the classical frameworks. ACS Appl Opt Mater 1:889–897. https://doi.org/10.1021/acsaom.3c00047

    Article  CAS  Google Scholar 

  8. Prusti B, Tripathi S, Jain A, Chakravarty M (2023) Concentration-guided visual detection of multiphase aliphatic biogenic amines through amine-phenol recognition using a dual-state emitter. ACS Appl Mater Interfaces 15:16492–16504. https://doi.org/10.1021/acsami.3c00791

    Article  CAS  PubMed  Google Scholar 

  9. Chen G, Li W, Zhou T, Peng Q, Zhai D, Li H, Yuan WZ, Zhang Y, Tang BZ (2015) Conjugation-Induced Rigidity in twisting Molecules: filling the gap between aggregation-caused Quenching and Aggregation-Induced Emission. Adv Mater 27:4496–4501. https://doi.org/10.1002/adma.201501981

    Article  CAS  PubMed  Google Scholar 

  10. Naito H, Nishino K, Morisaki Y, Tanaka K, Chujo Y (2017) Solid-state Emission of the Anthracene-o-Carborane Dyad from the twisted-intramolecular charge transfer in the Crystalline State. Angew Chem Int Ed 56:254–259. https://doi.org/10.1002/anie.201609656

    Article  CAS  Google Scholar 

  11. Wu H, Chen Z, Chi W, Bindra AK, Gu L, Qian C, Wu B, Yue B, Liu G, Yang G, Zhu L, Zhao Y (2019) Structural Engineering of Luminogens with High Emission Efficiency both in solution and in the solid state. Angew Chem Int Ed 58:11419–11423. https://doi.org/10.1002/anie.201906507

    Article  CAS  Google Scholar 

  12. Cui L, Gong Y, Cheng C, Guo Y, Xiong W, Ji H, Jiang L, Zhao J, Che Y (2021) Highly photostable and luminescent donor-acceptor molecules for Ultrasensitive Detection of Sulfur Mustard. Adv Sci 8:2002615. https://doi.org/10.1002/advs.202002615

    Article  CAS  Google Scholar 

  13. Stoerkler T, Pariat T, Laurent AD, Jacquemin D, Ulrich G, Massue J (2022) Excited-state intramolecular Proton transfer dyes with dual-state Emission Properties: Concept, examples and applications. Molecules 27:2443. https://doi.org/10.3390/molecules27082443

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Huber A, Dubbert J, Scherz TD, Voskuhl J (2022) Design concepts for solution and solid-state Emitters -A modern viewpoint on classical and non-classical approaches. Chem Eur J e202202481. https://doi.org/10.1002/chem.202202481

  15. Ge YQ, Jia J, Yang H, Tao XT, Wang JW (2011) The synthesis, characterization and Optical Properties of Novel Pyrido[1,2-a]benzimidazole derivatives. Dyes Pigm 88:344–349. https://doi.org/10.1016/j.dyepig.2010.08.005

    Article  CAS  Google Scholar 

  16. Ge Y, Wei P, Wang T, Cao X, Zhang D, Li FA (2018) Simple fluorescent probe for monitoring pH in Cellsbased on New Fluorophore pyrido[1,2-a]Benzimidazole. Sens Actuators B 254:314–320. https://doi.org/10.1016/j.snb.2017.07.060

    Article  CAS  Google Scholar 

  17. Ge Y, Zheng X, Ji R, Shen S, Cao XA (2017) New Pyrido[1,2-a]benzimidazole-Rhodamine FRET system as an efficient Ratiometric fluorescent probe for Cu2+ in living cells. Anal Chim Acta 965:103–110. https://doi.org/10.1016/j.aca.2017.02.006

    Article  CAS  PubMed  Google Scholar 

  18. Ge Y, Liu A, Ji R, Shen S, Cao X (2017) Detection of Hg2+ by a FRET Ratiometric fluorescent probe based on a Novel Pyrido[1,2-a]Benzimidazole-Rhodamine System. Sens Actuators B 251:410–415. https://doi.org/10.1016/j.snb.2017.05.097

    Article  CAS  Google Scholar 

  19. Liu A, Ji R, Shen S, Cao X, Ge YA (2017) Ratiometric fluorescent probe for sensing Sulfite based on a Pyrido[1,2-a]Benzimidazole Fluorophore. New J Chem 41:10096–10100. https://doi.org/10.1039/C7NJ02086D

    Article  CAS  Google Scholar 

  20. Zhang D, Liu A, Ji R, Dong J, Ge YA, Mitochondria-Targeted (2019) FRET-Based Ratiometric fluorescent probe for detection of SO2 derivatives in Water. Anal Chim Acta 1055:133–139. https://doi.org/10.1016/j.aca.2018.12.042

    Article  CAS  PubMed  Google Scholar 

  21. Zhang G, Ji R, Kong X, Ning F, Liu A, Cui J, Ge Y (2019) A FRET based Ratiometric fluorescent probe for detection of Sulfite in Food. RSC Adv 9:1147–1150. https://doi.org/10.1039/C8RA08967A

    Article  ADS  CAS  PubMed  PubMed Central  Google Scholar 

  22. Song G, Liu A, Jiang H, Ji R, Dong J, Ge Y (2019) A FRET-Based Ratiometric fluorescent probe for detection of intrinsically generated SO2 derivatives in Mitochondria. Anal Chim Acta 1053:148–154. https://doi.org/10.1016/j.aca.2018.11.052

    Article  CAS  PubMed  Google Scholar 

  23. Zong L, Xie Y, Wang C, Li JR, Li Q, Li Z (2016) From ACQ to AIE: the suppression of the strong π-π Interaction of Naphthalene Diimide derivatives through the Adjustment of their flexible chains. Chem Commun 52:11496–11499. https://doi.org/10.1039/C6CC06176A

    Article  CAS  Google Scholar 

  24. Bhuin S, Sharma P, Chakraborty P, Kulkarni OP, Chakravarty M (2023) Solid-state emitting twisted p-conjugate as AIE-active DSE-gen: in vitro anticancer properties against FaDu and 4T1 with biocompatibility and bioimaging. J Mater Chem B 11:188–203. https://doi.org/10.1039/D2TB02078E

    Article  CAS  Google Scholar 

Download references

Funding

This research was supported by the Natural Science Foundation of Shandong Province (ZR2021MB033), Incubation Program of Youth Innovation of Shandong Province, and the Innovative Research Programs of Higher Education of Shandong Province (2019KJC009).

Author information

Authors and Affiliations

Authors

Contributions

Yongchao Li, Liqing Zhang and Xianfeng Meng performed the experiments. Guowei Shi and Wei Gao helped with the characterization of the compounds. Guiyun Duan conducted the data analysis and wrote the paper. Yanqing Ge conceived and directed the project. All authors reviewed the manuscript.

Corresponding authors

Correspondence to Guiyun Duan or Yanqing Ge.

Ethics declarations

Ethical Approval

Not applicable.

Competing Interests

The authors declare that they have no known 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.

Electronic Supplementary Material

Below is the link to the electronic supplementary material.

Supplementary Material 1

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, Y., Zhang, L., Meng, X. et al. Visible-light Excited and Highly Photostable Organic Fluorophore with dual-state Emission. J Fluoresc 34, 829–832 (2024). https://doi.org/10.1007/s10895-023-03305-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-023-03305-0

Keywords

Navigation