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Substituent Effects on Fluorescence Properties of AIEgens Based on Coumarin-3-formylhydrazone and their Application in Cell Imaging

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Abstract

AIE-active compounds have lately attracted considerable attention owing to their versatile applications, especially in OLED and bioimaging. Herein, a series of coumarin-3-formylhydrazone derivatives (CFH-1, 2, 3 and 4) were developed for investigating their AIE and solid-state luminescence behaviors. All the obtained compounds emit varying degrees of solid-state fluorescence. CFH-1 and 2 show the typical AIE characteristics, while CFH-3 and 4 exhibit stronger solution fluorescence than their aggregation-induced emission. The single crystal X-ray diffraction analysis of CFH-1 and CFH-3 showed that both of them adopt planar conformation and the CH···O hydrogen bonding plays a crucial role in their crystal packing. Meanwhile, there is a notable difference between them. Successive π-π stacking interaction was observed in the crystal packing of CFH-1, while the crystals of CFH-3 contain dimeric π-π stacking interaction. Their distinct crystal packing interactions result in their different fluorescence properties. Moreover, both CFH-1 and CFH-2 displayed excellent bioimaging performances in living cells.

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Availability of Data and Material

The data supporting the findings of this study are included in this published article and its supplementary information files. The raw data are available from the corresponding author on reasonable request.

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References

  1. Wan Q, Tong J, Zhang B, Li Y, Wang Z, Tang BZ (2020) Exploration of high efficiency AIE-active deep/near infrared red emitters in OLEDs with high-radiance. Adv Optical Mater 8:1901520. https://doi.org/10.1002/adom.201901520

    Article  CAS  Google Scholar 

  2. Qian J, Tang BZ (2017) AIE lumigens for bioimaging and theranostics: from organelles to animals. Chem 3:56–91. https://doi.org/10.1016/j.chempr.2017.05.010

    Article  CAS  Google Scholar 

  3. Gao M, Tang BZ (2020) AIE-based cancer theranostics. Coordin. Chem Rev 402:213076. https://doi.org/10.1016/j.ccr.2019.213076

    Article  CAS  Google Scholar 

  4. Wang D, Lee MMS, Xu W, Kwok RTK, Lam JWY, Tang BZ (2018) Theranostics based on AIEgens. Theranostics 8:4925–4956. https://doi.org/10.7150/thno.27787

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Xiong JB, Yuan YX, Wang L, Sun JP, Qiao WG, Zhang HC, Duan M, Han H, Zhang S, Zheng YS (2018) Evidence for aggregation-induced emission from free rotation restriction of double bond at excited state. Org Lett 20:373–376. https://doi.org/10.1021/acs.orglett.7b03662

    Article  CAS  PubMed  Google Scholar 

  6. Abedi SAA, Chi W, Tan D, Shen T, Wang C, Ang ECX, Tan CH, Anariba F, Liu X (2021) Restriction of twisted intramolecular charge transfer enables the aggregation-induced emission of 1-(N, N-dialkylamino)-naphthalene derivatives. J Phys Chem A 125:8397–8403. https://doi.org/10.1021/acs.jpca.1c06263

    Article  CAS  PubMed  Google Scholar 

  7. Tu Y, Liu J, Zhang H, Peng Q, Lam JWY, Tang BZ (2019) Restriction of access to the dark state: a new mechanistic model for heteroatom-containing AIE systems. Angew Chem Int Ed 58:14911–14914. https://doi.org/10.1002/anie.201907522

    Article  CAS  Google Scholar 

  8. 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 

  9. Li Q, Niu ZG, Liu YL, Wang EJ (2020) Crystal structure and aggregation-induced emission of an azine derivative. Chin J Struct Chem 39:693–697. https://doi.org/10.14102/j.cnki.0254-5861.2011-2464

    Article  CAS  Google Scholar 

  10. Han X, Ma Y, Chen Y, Wang X, Wang Z (2020) Enhancement of the aggregation-induced emission by hydrogen bond for visualizing hypochlorous acid in an inflammation model and a hepatocellular carcinoma model. Anal Chem 92:2830–2838. https://doi.org/10.1021/acs.analchem.9b05347

    Article  CAS  PubMed  Google Scholar 

  11. Shih KY, Lin YC, Hsiao TS, Deng SL, Kuo SW, Hong JL (2014) Amorphous and crystalline blends from polytyrosine and pyridine-functionalized anthracene: hydrogen-bond interactions, conformations, intramolecular charge transfer and aggregation-induced emission. Polym Chem 5:5765–5774. https://doi.org/10.1039/C4PY00706A

    Article  CAS  Google Scholar 

  12. Wang L, Qin Y, Cheng Y, Fan W, Yang S, Zheng L, Cao Q (2022) Intermolecular hydrogen bonds induce restriction of access to the dark state for triggering aggregation-induced emission. J Mater Chem C 10:5356–5363. https://doi.org/10.1039/D2TC00085G

    Article  CAS  Google Scholar 

  13. Yang HL, Zhang QP, Zhang YM, Gong GF, Che YY, Zhou Q, Yao HG, Wei TB, Lin Q (2019) A novel strong AIE bi-component hydrogel as a multi-functional supramolecular fluorescent material. Dyes Pigm 171:107745. https://doi.org/10.1016/j.dyepig.2019.107745

    Article  CAS  Google Scholar 

  14. Zhao R, Zhang M, Liu Y, Zhang X, Duan Y, Han T (2020) Fabricating D-A type AIE luminogen into film sensor for turn-on detection of methanol vapour. Sensor Actuat B 319:128323. https://doi.org/10.1016/j.snb.2020.128323

    Article  CAS  Google Scholar 

  15. Yang J, Yang B, Wen G, Liu B (2019) Dual sites fluorescence probe for H2S and Hg2+ with AIE transformers function. Sensor Actuat B 296:126670. https://doi.org/10.1016/j.snb.2019.126670

    Article  CAS  Google Scholar 

  16. He G, Li J, Wang Z, Liu C, Liu X, Ji L, Xie C, Wang Q (2017) Synthesis of a fluorogenic probe for thiols based on a coumarin Schiff base copper complex and its use for the detection of glutathione. Tetrahedron 73:272–277. https://doi.org/10.1016/j.tet.2016.12.012

    Article  CAS  Google Scholar 

  17. Shen Y, Zhang Z, Liu H, Yan Y, Zhang S, Yang B, Ma Y (2019) Highly-efficient orange-red/red excimer fluorescence from dimeric π-π stacking of perylene and its nanoparticles application. J Phys Chem C 123:13047–13056. https://doi.org/10.1021/acs.jpcc.9b02447

    Article  CAS  Google Scholar 

  18. Shen Y, Liu H, Zhang S, Gao Y, Li B, Yan Y, Hu Y, Zhao L, Yang B (2017) Discrete face-to-face stacking of anthracene inducing high-efficiency excimer fluorescence in solids via a thermally-activated phase transition. J Mater Chem C 5:10061–10067. https://doi.org/10.1039/C7TC03229C

    Article  CAS  Google Scholar 

  19. Liu H, Yao L, Li B, Chen X, Gao Y, Zhang S, Li W, Lu P, Yang B, Ma Y (2016) Excimer-induced high-efficiency fluorescence due to pairwise anthracene stacking in crystal with long lifetime. Chem Commun 52:7356–7359. https://doi.org/10.1039/C6CC01993E

    Article  CAS  Google Scholar 

  20. Liu H, Cong D, Li B, Ye L, Ge Y, Tang X, Shen Y, Wen Y, Wang J, Zhou C, Yang B (2017) Discrete dimeric anthracene stackings in solids with enhanced excimer fluorescence. Cryst Growth Des 17:2945–2949. https://doi.org/10.1021/acs.cgd.7b00460

    Article  CAS  Google Scholar 

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Funding

This work is financially supported by Hainan Provincial Natural Science Foundation of China (222MS059) and the National Natural Science Foundation of China (22061016).

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Authors and Affiliations

  1. Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou, 571158, China

    Panpan Chen, Yang Zhao, Zhigang Niu & Enju Wang

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  1. Panpan Chen
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  2. Yang Zhao
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  3. Zhigang Niu
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  4. Enju Wang
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Contributions

EW contributed to the study conception and design, and was the major contributor in writing the manuscript. The synthesis, spectrum test, data analysis and so on were performed by PC with the assistance of YZ. The X-ray diffraction data collection and structure determination was performed by ZN.

The crystallographic information files that have been deposited in the Cambridge Crystallographic Data Centre (CCDC 2,178,542 and 2,178,543) which are freely available for all. The link for CCDC: https://www.ccdc.cam.ac.uk/.

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Correspondence to Enju Wang.

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Chen, P., Zhao, Y., Niu, Z. et al. Substituent Effects on Fluorescence Properties of AIEgens Based on Coumarin-3-formylhydrazone and their Application in Cell Imaging. J Fluoresc 33, 663–669 (2023). https://doi.org/10.1007/s10895-022-03103-0

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