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Seminaphthorhodafluor Derivatives Bridged Periodic Mesoporous Organosilicas for Detection of Cu2+

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Abstract

Seminaphthorhodafluor (SNARF) Schiff base (SNARF-SB) bridged periodic mesoporous organosilicas (SSPMOs) with “turn-on” fluorescence enhancement for sensing Cu2+ were synthesized via a template-directed co-condensation method. Small-angle x-ray scattering (SAXS) patterns, high resolution transmission electron microscope (HRTEM) images, and N2 adsorption–desorption isotherms indicated the presence of mesoporous structure in the SSPMOs. FT-IR spectra and 29Si MAS NMR data confirmed the successful incorporation of bridged organic groups in the framework of SSPMOs. The luminous properties that SSPMOs had a selective response to Cu2+ were investigated by UV–Vis absorption spectroscopy and fluorescence spectroscopy. The limit of detection (LOD) was 5.1 × 10–7 M and binding stoichiometry was determined 1:1 between SNARF-SB and Cu2+. The fluorescence enhancement of SSPMOs towards Cu2+ was induced by ring-opening of the spirolactam in SNARF-SB in framework of SSPMOs, which was confirmed by FT-IR spectra of SNARF-SB with Cu2+. Moreover, SSPMOs have improved fluorescence lifetimes compared with that of SNARF-SB. Therefore, SSPMOs can be a progressive chemical sensor for Cu2+ due to its high selectivity, recyclability, and stability.

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Data Availability

The datasets generated during the current study are available from the corresponding author on reasonable request.

References

  1. Wu D, Sedgwick AC, Gunnlaugsson T, Akkaya EU, Yoon J, James TD (2017) Fluorescent chemosensors: the past, present and future. Chem Soc Rev 46:7105–7123. https://doi.org/10.1039/c7cs00240h

    Article  CAS  Google Scholar 

  2. AbhijnaKrishna R, Velmathi S (2022) A review on fluorimetric and colorimetric detection of metal ions by chemodosimetric approach 2013–2021. Coord Chem Rev. https://doi.org/10.1016/j.ccr.2021.214401

    Article  Google Scholar 

  3. Capon PK, Li J, Horsfall AJ, Yagoub S, Schartner EP, Khalid A, Kirk RW, Purdey MS, Dunning KR, McLaughlin RA, Abell AD (2021) A Silk-Based Functionalization Architecture for Single Fiber Imaging and Sensing. Adv Funct Mater. https://doi.org/10.1002/adfm.202010713

    Article  Google Scholar 

  4. Wei D, Engelman DM, Reshetnyak YK, Andreev OA (2019) Mapping pH at Cancer Cell Surfaces. Mol Imaging Biol 21:1020–1025. https://doi.org/10.1007/s11307-019-01335-4

    Article  CAS  Google Scholar 

  5. Destino JF, Craft AK, Bright FV (2017) Three-Dimensional pH Mapping within Model Hybrid Xerogel Thin Films. Langmuir 33:4119–4128. https://doi.org/10.1021/acs.langmuir.6b04518

    Article  CAS  Google Scholar 

  6. Kuhana AT, Feng W, Feng G (2018) A simple but effective colorimetric and far-red to near-infrared fluorescent probe for palladium and its application in living cells. Dyes Pigm 152:112–117. https://doi.org/10.1016/j.dyepig.2018.01.044

    Article  CAS  Google Scholar 

  7. Jin X, Zhao S, Wang T, Si L, Liu Y, Zhao C, Zhou H, Leng X, Zhang X (2019) Near-infrared fluorescent probe for selective detection of H2S and its application in living animals. Anal Bioanal Chem 411:5985–5992. https://doi.org/10.1007/s00216-019-01973-1

    Article  CAS  Google Scholar 

  8. Duan Q, Zhu H, Liu C, Yuan R, Fang Z, Wang Z, Jia P, Li Z, Sheng W, Zhu B (2019) A carbonothioate-based far-red fluorescent probe for the specific detection of mercury ions in living cells and zebrafish. Analyst 144:1426–1432. https://doi.org/10.1039/c8an01696h

    Article  CAS  Google Scholar 

  9. Zeng X, Gao S, Jiang C, Jin X, Ma M, Liu Z, Chen J (2021) A Colorimetric and Long-Wavelength “Turn-On” Fluorescent Probe for Copper Ions Detection with High Selectivity and Sensitivity. ChemistrySelect 6:6619–6624. https://doi.org/10.1002/slct.202101520

    Article  CAS  Google Scholar 

  10. Jia X, Li X, Geng X, Nie C, Zhang P, Wei C, Li X (2019) A seminaphthorhodafluor-based near-infrared fluorescent probe for hydrazine and its bioimaging in living systems. Spectrochim Acta A Mol Biomol Spectrosc 223:117307. https://doi.org/10.1016/j.saa.2019.117307

    Article  CAS  Google Scholar 

  11. Zhu H, Liu C, Yuan R, Wang R, Zhang H, Li Z, Jia P, Zhu B, Sheng W (2019) A simple highly specific fluorescent probe for simultaneous discrimination of cysteine/homocysteine and glutathione/hydrogen sulfide in living cells and zebrafish using two separated fluorescence channels under single wavelength excitation. Analyst 144:4258–4265. https://doi.org/10.1039/c9an00818g

    Article  CAS  Google Scholar 

  12. Li H, Shen D, Lu H, Wu F, Chen X, Pleixats R, Pan J (2021) The synthetic approaches, properties, classification and heavy metal adsorption applications of periodic mesoporous organosilicas. Sep Purif Technol. https://doi.org/10.1016/j.seppur.2021.119453

    Article  Google Scholar 

  13. Karimi B, Ganji N, Pourshiani O, Thiel WR (2022) Periodic mesoporous organosilicas (PMOs): From synthesis strategies to applications. Prog Mater Sci. https://doi.org/10.1016/j.pmatsci.2021.100896

    Article  Google Scholar 

  14. Gao M, Xing C, Jiang X, Xu L, Li P, Hsiao CD (2021) Highly selective fluorescence detection of Cu2+ based on Schiff base functionalized periodic mesoporous organosilicas. Luminescence 36:951–957. https://doi.org/10.1002/bio.4021

    Article  CAS  Google Scholar 

  15. Hao X, Han S, Zhu J, Hu Y, Chang LY, Pao CW, Chen JL, Chen JM, Haw SC (2019) A bis-benzimidazole PMO ratiometric fluorescence sensor exhibiting AIEE and ESIPT for sensitive detection of Cu2+. RSC Adv 9:13567–13575. https://doi.org/10.1039/c9ra00892f

    Article  CAS  Google Scholar 

  16. Zhou A, Han S (2021) An “off-on-off” fluorescence chemosensor for the sensitive detection of Cu2+ in aqueous solution based on multiple fluorescence emission mechanisms. Analyst 146:2670–2678. https://doi.org/10.1039/d0an02472d

    Article  CAS  Google Scholar 

  17. Li H, Li Y, Zhang Z, Pang X, Yu X (2019) Highly selective luminescent sensing of Cu2+ in aqueous solution based on a Eu(III)-centered periodic mesoporous organosilicas hybrid. Mater Des. https://doi.org/10.1016/j.matdes.2019.107712

    Article  Google Scholar 

  18. Liu W, Kaczmarek AM, Rijckaert H, Van Der Voort P, Van Deun R (2021) Chemical sensors based on a Eu(iii)-centered periodic mesoporous organosilica hybrid material using picolinic acid as an efficient secondary ligand. Dalton Trans 50:11061–11070. https://doi.org/10.1039/d1dt01767e

    Article  CAS  Google Scholar 

  19. Jiao X, Liu C, Huang K, Zhang S, He S, Zhao L, Zeng X (2015) Molecular design and synthesis of a pH independent and cell permeant fluorescent dye and its applications. Org Biomol Chem 13:6647–6653. https://doi.org/10.1039/c5ob00448a

    Article  CAS  Google Scholar 

  20. Mondal S, Manna SK, Pathak S, Ghosh A, Datta P, Mandal D, Mukhopadhyay S (2020) A “turn-on” fluorescent and colorimetric chemodosimeter for selective detection of Au3+ ions in solution and in live cells via Au3+-induced hydrolysis of a rhodamine-derived Schiff base. New J Chem 44:7954–7961. https://doi.org/10.1039/d0nj01273d

    Article  CAS  Google Scholar 

  21. Jiang D, Yang Q, Wang H, Zhu G, Yang J, Li C (2006) Periodic mesoporous organosilicas with trans-(1R,2R)-diaminocyclohexane in the framework: A potential catalytic material for asymmetric reactions. J Catal 239:65–73. https://doi.org/10.1016/j.jcat.2006.01.018

    Article  CAS  Google Scholar 

  22. Pereira C, Alves C, Monteiro A, Magen C, Pereira AM, Ibarra A, Ibarra MR, Tavares PB, Araujo JP, Blanco G, Pintado JM, Carvalho AP, Pires J, Pereira MF, Freire C (2011) Designing novel hybrid materials by one-pot co-condensation: from hydrophobic mesoporous silica nanoparticles to superamphiphobic cotton textiles. ACS Appl Mater Interfaces 3:2289–2299. https://doi.org/10.1021/am200220x

    Article  CAS  Google Scholar 

  23. Tang R, Lei K, Chen K, Zhao H, Chen J (2011) A rhodamine-based off-on fluorescent chemosensor for selectively sensing Cu(II) in aqueous solution. J Fluoresc 21:141–148. https://doi.org/10.1007/s10895-010-0698-x

    Article  CAS  Google Scholar 

  24. Muthusamy S, Rajalakshmi K, Kannan P, Zhu D, Seo Y, Zhu W, Song J-W, Lee K-B, Nam Y-S (2022) Targeting citrate as novel strategy in diagnosing prostate cancer using Rhodamine extended red emissive fluorophore: Sensing mechanism and prostate tumor diagnosis applications. Sens Actuators B. https://doi.org/10.1016/j.snb.2022.132299

    Article  Google Scholar 

  25. Huang K, Liu Y, Li Q, Yu B, Liang L, Qin D (2022) A quinoline-rhodamine hybrid probe for ratiometricly sensing of Hg2+ in water and cell imaging application. Spectrochim Acta A Mol Biomol Spectrosc 281:121651. https://doi.org/10.1016/j.saa.2022.121651

    Article  CAS  Google Scholar 

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Acknowledgements

All authors are very grateful for the support of Center for Structural and Property Analysis of Shandong University.

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Yangyang Ren designed the research, carried out experiments and wrote the main manuscript. Shuhua Han designed the research, supervised the findings of the research and reviewed the manuscript. All authors made contribution to the final manuscript.

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Correspondence to Shuhua Han.

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Ren, Y., Han, S. Seminaphthorhodafluor Derivatives Bridged Periodic Mesoporous Organosilicas for Detection of Cu2+. J Fluoresc 33, 327–337 (2023). https://doi.org/10.1007/s10895-022-03059-1

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