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AIE Stereoisomers with Huge Differences in Luminescence Behavior and Biomedical Activity

preprint
submitted on 18.05.2020 and posted on 20.05.2020 by Xuewen He, Ryan Tsz Kin Kwok, Jacky W. Y. Lam, Ben Zhong Tang
Stereoisomers that differ only in spatial orientation of their atoms could exhibit distinctive properties and have attracted immense interest in drug development and material science. Herein, a series of AIE-featured stereoisomers with pronounced difference in luminescent and biomedical activities were efficiently synthesized and easily purified. One of the isomers in the E/Z pair is emissive with high fluorescence quantum yield at room temperature, while the other one is nearly non-emissive. As the isomers could transform between each other under UV irradiation, the light-up cell imaging was successfully demonstrated using the non-emissive isomer as a turn-on probe via isomerization process. Analysis of crystal packing patterns illustrated that the contrasts in void space possibly caused the difference in molecular motion and thus led to their distinct luminescence properties. Further, the E/Z isomers displayed remarkable difference in enzymatic conversion rates and cellular toxicities for several cancer cell lines. The distinctive luminescence properties of the isomeric pair provided a powerful tool to image those divergencies in biomedical activity, holding great potential for visualizable drug screening and development.

Funding

the Research Grants Council of Hong Kong (C6009-17G), the Innovation and Technology Commission (ITC-CNERC14SC01), the National Natural Science Foundation of China (21788102), the Natural Science Foundation of Guangdong Province (2019B030301003), and the National Key Research and Development program of China (2018YFE0190200).

History

Email Address of Submitting Author

xheao@connect.ust.hk

Institution

The Hong Kong University of Science and Technology

Country

China

ORCID For Submitting Author

0000-0002-8414-5164

Declaration of Conflict of Interest

no conflict of interest

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