Functionalized Acrylonitriles with Aggregation-Induced Emission: Structure Tuning by Simple Reaction-Condition Variation, Efficient Red Emission, and Two-Photon Bioimaging

Guangle Niu, Xiuli Zheng, Zheng Zhao, Haoke Zhang, Jianguo Wang, Xuewen He, Yuncong Chen, Xiujuan Shi, Chao Ma, Ryan T.K. Kwok, Jacky W.Y. Lam, Herman H.Y. Sung, Ian D. Williams, Kam Sing Wong, Pengfei Wang, Ben Zhong Tang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

163 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)15111-15120
Number of pages10
JournalJournal of the American Chemical Society
Volume141
Issue number38
DOIs
Publication statusPublished - 25 Sept 2019
Externally publishedYes

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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. (2019). Functionalized Acrylonitriles with Aggregation-Induced Emission: Structure Tuning by Simple Reaction-Condition Variation, Efficient Red Emission, and Two-Photon Bioimaging. Journal of the American Chemical Society, 141(38), 15111-15120. https://doi.org/10.1021/jacs.9b06196