Functionalized Acrylonitriles with Aggregation-Induced Emission: Structure Tuning by Simple Reaction-Condition Variation, Efficient Red Emission, and Two-Photon Bioimaging
Abstract
Acrylonitriles with aggregation-induced emission (AIE) characteristics have been found to show promising applications in two-photon biomedical imaging. Generally, elaborate synthetic efforts are required to achieve different acrylonitriles with distinct functionalities. In this work, we first reported the synthesis of two different group-functionalized AIE-active acrylonitriles (TPAT-AN-XF and 2TPAT-AN) obtained simply by mixing the same reactants at different temperatures using a facile and transition metal-free synthetic method. These two AIE luminogens (AIEgens) exhibit unique properties such as bright red emission in the solid state, large Stokes shift, and large two-photon absorption cross section. Water-soluble nanoparticles (NPs) of 2TPAT-AN were prepared by a nanoprecipitation method. In vitro imaging data show that 2TPAT-AN NPs can selectively stain lysosome in live cells. Besides one-photon imaging, remarkable two-photon imaging of live tumor tissues can be achieved with high resolution and deep tissue penetration. 2TPAT-AN NPs show high biocompatibility and are successfully utilized in in vivo long-term imaging of mouse tumors with a high signal-to-noise ratio. Thus, the present work is anticipated to shed light on the preparation of a library of AIE-active functionalized acrylonitriles with intriguing properties for biomedical applications.
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Self-citation
- Authors
- Niu, G., Zheng, X., Zhao, Z., Zhang, H., Wang, J., He, X., Chen, Y., Shi, X., Ma, C., Kwok, R. T. K., Lam, J. W. Y., Sung, H. H. Y., Williams, I. D., Wong, K. S., Wang, P., & Tang, B. Z.
- Affiliations
- Hong Kong University of Science and Technology (HK)
- Chinese Academy of Sciences (CN)
- Corresponding author
- Tang, Ben Zhong
- ORCID
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2019-08-22
- Volume
- 141
- Issue
- 38
- Pages
- 15111-15120
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2969983440
- Cited by
- 183
- References
- 70
- Citations by year
- 2026: 7 · 2025: 5 · 2024: 16 · 2023: 30 · 2022: 38 · 2021: 43 · 2020: 35 · 2019: 9
- FWCI
- 11.28
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- Locations
- Journal of the American Chemical Society (publishedVersion)
- PubMed (publishedVersion)
- Rare & Special e-Zone (The Hong Kong University of Science and Technology) (submittedVersion)
- Funders
- Research Grants Council, University Grants Committee (16305015, A-HKUST 605/16, C6009-17G)
- University Grants Committee (AoE/P-02/12, AoE/P-03/08)
- Innovation and Technology Commission (ITC-CNERC14SC01)
- National Natural Science Foundation of China (21788102)
- Chinese Academy of Sciences (GJHZ1723, YJKYYQ20170015)
- Shenzhen Municipality (JCYJ20180507183832744, JCYJ20160229205601482, JCYJ20170818113840164, JCYJ20170818113851132, JCYJ20170818113538482)
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
- Physical Sciences › Engineering › Biomedical Engineering › Nonlinear Optical Materials Studies
- Keywords
- aggregation-induced emission, acrylonitrile, AIEgens, red emission, two-photon absorption, water-soluble nanoparticles, nanoprecipitation, tumor imaging, deep tissue imaging, transition-metal-free synthesis, temperature-dependent synthesis, structure tuning, biocompatibility
- MeSH terms
- Acrylonitrile, Fluorescent Dyes, Molecular Structure, Photons, Optical Imaging
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