Skip to main content
SpringerLink
Log in

Theoretical Insights on the Sensing Performance for Newly-synthesized Two-photon Fluorescent N2H4 Probes Based on Spirobifluorence

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

Abstract

The development of fluorescent probe for hydrazine (N2H4) detection has attracted much attention due to the important role of N2H4 plays in the fields of medicine, agriculture, biology and environments. In this paper, the optical properties and water solubility of two novel two-photon fluorescent molecular probes (Probe1 and Probe2) before and after the reaction with N2H4 are studied by using the density function theory. The results show that electronic distribution and transition dipole moment of the probes are obviously changed after the reaction with N2H4, thus the optical properties of the molecules are influenced and the detection of N2H4 are realized. In addition, photoinduced electron transfer processes for Probe1 and Probe2 in the presence of N2H4 are theoretically characterized, which explains the experimental observations from the microscopic mechanism. Special attention has been paid on the analysis of the two-photon absorption for the probes with the absence and presence of N2H4 by the response theory method. Both probes with good water solubility show large variation on the two-photon absorption cross section when reacts with N2H4. In particular, the two-photon absorption response of Probe2 is more obvious, so it possesses preferable two-photon fluorescence microscopic imaging ability. More importantly, the receptor effect on the sensing performances of the probes are demonstrated, providing a theoretical reference for the design and synthesis on more efficient two-photon fluorescence N2H4 probes. Our study provides necessary information on the response mechanism of the studied chemosensors and helps to establish the relationship between the structure and optical properties of two-photon fluorescence N2H4 probes.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9

Similar content being viewed by others

Data Availability

The data and materials are available within the manuscript.

References

  1. He L, Huang Y, Wang A, Wang X, Chen X, Delgado JJ, Zhang T (2012) A noble-metal-free catalyst derived from Ni-Al hydrotalcite for hydrogen generation from N2H4⋅H2O decomposition. Angew Chem Int Edit 51:6191–6194

    Article  CAS  Google Scholar 

  2. Tang T, Chen YQ, Fu BS, He ZY, Xiao H, Wu F, Wang JQ, Wang SR, Zhou X (2016) A novel resorufin based fluorescent “turn-on” probe for the selective detection of hydrazine and application in living cells. Chin Chem Lett 27:540–544

    Article  CAS  Google Scholar 

  3. Shi X, Huo F, Chao J, Yin C (2018) A ratiometric fluorescent probe for hydrazine based on novel cyclization mechanism and its application in living cells. Sensor Actuat B-Chemical 260:609–616

    Article  CAS  Google Scholar 

  4. Sanabria-Chinchilla J, Asazawa K, Sakamoto T, Yamada K, Strasser P (2011) Noble metal-free hydrazine fuel cell catalysts: Epoc effect in competing chemical and electrochemical reaction pathways. J Am Chem Soc 133:5425–5431

    Article  CAS  PubMed  Google Scholar 

  5. Wu G, Tang X, Ji W, Lai K, Tong Q (2017) A turn-on fluorescent probe based on coumarin-anhydride for highly sensitive detection of hydrazine in the aqueous solution and gas states. Methods Appl Fluores 5:015001

    Article  Google Scholar 

  6. Reilly CA, Aust SD (1997) Peroxidase substrates stimulate the oxidation of hydralazine to metabolites which cause single-strand breaks in DNA. Chem Res Toxicol 10:328–334

    Article  CAS  PubMed  Google Scholar 

  7. Chen S, Hou P, Wang J, Liu L, Zhang Q (2017) A highly selective fluorescent probe based on coumarin for the imaging of N2H4 in living cells. Spectrochim Acta A 173:170–174

    Article  CAS  Google Scholar 

  8. Xiao L, Tu J, Sun S, Pei Z, Pei Y, Pang Y, Xu Y (2014) A fluorescent probe for hydrazine and its in vivo applications. RSC Adv 4:41807–41811

    Article  CAS  Google Scholar 

  9. Xu W, Liu W, Zhou T, Yang Y, Li W (2018) A novel PBT-based fluorescent probe for hydrazine detection and its application in living cells. J Photoch Photobiolo A 356:610–616

    Article  CAS  Google Scholar 

  10. Liu Y, Ren D, Zhang J, Li H, Yang X-F (2019) A fluorescent probe for hydrazine based on a newly developed 1-indanone-fused coumarin scaffold. Dyes Pigment 162:112–119

    Article  CAS  Google Scholar 

  11. Zhou L, Li Y, Zhou A, Zhang G, Cheng ZQ, Ge YX, Liu SK, Azevedo RB, Zhang J, Jiang S, Jiang CS (2020) A new endoplasmic reticulum (Er)-targeting fluorescent probe for the imaging of cysteine in living cells. J Fluoresc 30:1357–1364

    Article  CAS  PubMed  Google Scholar 

  12. Zhang J, Ning L, Liu J, Wang J, Yu B, Liu X, Yao X, Zhang Z, Zhang H (2015) Naked-eye and near-infrared fluorescence probe for hydrazine and its applications in in vitro and in vivo bioimaging. Anal Chem 87:9101–9107

    Article  CAS  PubMed  Google Scholar 

  13. Hu C, Sun W, Cao J, Gao P, Wang J, Fan J, Song F, Sun S, Peng X (2013) A ratiometric near-infrared fluorescent probe for hydrazine and its in vivo applications. Org Lett 15:4022–4025

    Article  CAS  PubMed  Google Scholar 

  14. Ou-Yang J, Jiang WL, Tan KY, Liu HW, Li SJ, Liu J, Li YF, Li CY (2018) Two-photon fluorescence probe for precisely detecting endogenous H2S in lysosome by employing a dual lock system. Sensor Actuat B-Chemical 260:264–273

    Article  CAS  Google Scholar 

  15. Liu Y, Liu W, Li H, Yan W, Yang X, Liu D, Wang S, Zhang J (2018) Two-photon fluorescent probe for detection of nitroreductase and hypoxia-specific microenvironment of cancer stem cell. Anal Chim Acta 1024:177–186

    Article  CAS  PubMed  Google Scholar 

  16. Yu SL, Wang SX, Yu HZ, Feng Y, Zhang ST, Zhu MY, Yin H, Meng XM (2015) A ratiometric two-photon fluorescent probe for hydrazine and its applications. Sensors Actuat B-Chem 220:1338–1345

    Article  CAS  Google Scholar 

  17. Wang JY, Liu ZR, Ren M, Lin W (2017) 2-benzothiazoleacetonitrile based two-photon fluorescent probe for hydrazine and its bio-imaging and environmental applications. Sci Rep 7:1530

    Article  PubMed  PubMed Central  Google Scholar 

  18. Yan S, Guo H, Tan J, Jiang J, Xiao H (2020) Two novel spirobifluorene-based two-photon fluorescent probes for the detection of hydrazine in solution and living cells. Talanta 218:121210

    Article  CAS  PubMed  Google Scholar 

  19. Leng J, Xin J, Zhou H, Li K, Hu W, Zhang Y (2021) Theoretical insights into sensing performances of rhodamine-contained two-photon fluorescent probes for mercury ion. Inter J Quantum Chem 121:e26435

    Article  CAS  Google Scholar 

  20. Liu XT, Zou LY, Ren AM, Guo JF, Sun Y, Huang S, Feng JK (2011) Theoretical investigation of one- and two-photon spectra of pyrazabole chromophores. Theor Chem Acc 130:37

    Article  CAS  Google Scholar 

  21. Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R, Scalmani G, Barone V, Petersson G A, Nakatsuji H, Li X, Caricato M, Marenich A V, Bloino J, Janesko B G, Gomperts R, Mennucci B, Hratchian H P, Ortiz J V, Izmaylov A F, Sonnenberg J L, Williams, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski V G, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery Jr. J A, Peralta J E, Ogliaro F, Bearpark M J, Heyd J J, Brothers E N, Kudin K N, Staroverov V N, Keith T A, Kobayashi R, Normand J, Raghavachari K, Rendell A P, Burant J C, Iyengar S S, Tomasi J, Cossi M, Millam J M, Klene M, Adamo C, Cammi R, Ochterski J W, Martin R L, Morokuma K, Farkas O, Foresman JB, Fox DJ (2016). Gaussian 16 rev. C.01. (Wallingford, CT)

  22. Dalton (2013) References in https://daltonprogram.org/. Accessed 7 Jul 2021

  23. Cancès E, Mennucci B, Tomasi J (1997) A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics. J Chem Phys 107:3032–3041

    Article  Google Scholar 

  24. Cossi M, Barone V, Mennucci B, Tomasi J (1998) Ab initio study of ionic solutions by a polarizable continuum dielectric model. Chem Phys Lett 286:253–260

    Article  CAS  Google Scholar 

  25. Chi WJ, Sun PP, Li ZS (2016) A strategy to improve the efficiency of hole transporting materials: Introduction of a highly symmetrical core. Nanoscale 8:17752–17756

    Article  CAS  PubMed  Google Scholar 

  26. Marenich AV, Cramer CJ, Truhlar DG (2009) Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. J Phys Chem B 113:6378–6396

    Article  CAS  PubMed  Google Scholar 

  27. Guo XH, Yu LB, Hao XL, He TF, Guo JF, Wei X, Cui WB, Yu LY, Qu ZX, Ren AM (2021) Theoretical study of a two-photon fluorescent probe based on nile red derivatives with controllable fluorescence wavelength and water solubility. J Chem Inf Model 61:5082–5097

    Article  CAS  PubMed  Google Scholar 

  28. Kelly CP, Cramer CJ, Truhlar DG (2005) Sm6: A density functional theory continuum solvation model for calculating aqueous solvation free energies of neutrals, ions, and solute−water clusters. J Chem Theory Comput 1:1133–1152

    Article  CAS  PubMed  Google Scholar 

Download references

Funding

This work was supported by the Natural Science Foundation of Shandong Province of China (No. ZR2020MA081) and Research Leader Program of Jinan Science and Technology Bureau ( No. 2019GXRC061).

Author information

Author notes

  1. Tengfei Jiang and Ni Luan are contributed equally to this work.

Authors and Affiliations

  1. International School for Optoelectronic Engineering, Qilu University of Technology (Shandong Academy of Sciences), Jinan, 250353, China

    Tengfei Jiang, Ni Luan, Longping Wang, Jiancai Leng & Yujin Zhang

Authors
  1. Tengfei Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ni Luan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Longping Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jiancai Leng
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yujin Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

Methodology: Jiancai Leng and Yujin Zhang; Investigation: Tengfei Jiang and Ni Luan; Writing—original draft preparation: Tengfei Jiang, Ni Luan and Longping Wang; Writing—review and editing: Jiancai Leng and Yujin Zhang; Supervision: Jiancai Leng and Yujin Zhang.

Corresponding authors

Correspondence to Jiancai Leng or Yujin Zhang.

Ethics declarations

Ethics Approval

Not applicable.

Consent to Participate

Not applicable.

Consent to Publish

Not applicable.

Conflicts of Interest

No relevant financial or non-financial interests to disclose. 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.

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

Jiang, T., Luan, N., Wang, L. et al. Theoretical Insights on the Sensing Performance for Newly-synthesized Two-photon Fluorescent N2H4 Probes Based on Spirobifluorence. J Fluoresc 33, 1949–1959 (2023). https://doi.org/10.1007/s10895-023-03209-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-023-03209-z

Keywords

Search

Navigation