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Polymerizable AEE-active Dye with Optical Activity for Fluorescent Nanoparticles Based on Phenothiazine: Synthesis, Self-assembly and Biological Imaging

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Abstract

In consideration of various advantages such as less harm, higher sensitivity, and deeper imaging depth, etc., AIE materials with longwave emission are attracting extensive attention in the fields of vascular visualization, organelle imaging, cells tracker, forensic detection, bioprobe and chemosensor, etc. In this work, a novel fluorescent (R)-PVHMA monomer with chirality and aggregation-induced emission enhancement (AEE) characteristics was acquired through enzymatic transesterification reaction basing on phenothiazine, and its [α] 25°CD value was about −6.39° with a 3.08 eV bandgap calculated by the quantum calculations. Afterwards, a series of PEG-PVH1 and PEG-PVH2 copolymers with chirality feature were achieved through RAFT polymerization of the obtained (R)-PVHMA and PEGMA with various feed ratios. When the feed molar ratio of (R)-PVHMA increased from 21.5% to 29.6%, its actual molar fractions in the PEG-PVH1 and PEG-PVH2 copolymers accordingly increased from 18.1% to 25.7%. The molecular weight of PEG-PVH1 was about 2.2×104 with a narrow PDI, and their kinetics estimation showed a first-order quasilinear procedure. In aqueous solution, the amphiphilic copolymers PEG-PVH could self-assemble into about 100 nm nanoparticles. In a 90% water solution of H2O and THF mixture, the fluorescence intensity had the maximum value, and the emission wavelength presented at 580 and 630 nm. The investigation of cytotoxicity and cells uptake showed that PEG-PVH FONs performed outstanding biocompatibility and excellent cells absorption effects, which have great potential in bioimaging application.

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Acknowledgments

This work was financially supported by the Natural Science Foundation of Guangdong Province (Nos. 2018A030313784 and 2021A1515410008), the Colleges and Universities Projects of Guangdong Province (Nos. 2020KTSCX180, 2020KTSCX184 and 2020ZDZX3027), the National Natural Science Foundation of China (No. 51673107) and the Climbing Plan of Guangdong Province (No. PDJH2021a0616).

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Authors and Affiliations

  1. School of Materials & Food Engineering, Zhongshan Institute, University of Electronic Science & Technology of China, Zhongshan, 528402, China

    Zeng-Fang Huang, Ya-Li Chen, Chao-Yue Zhou, Yan-Hong Li & Mei Li

  2. School of Materials and Energy, University of Electronic Science & Technology of China, Chengdu, 610054, China

    Zeng-Fang Huang, Ya-Li Chen, Chao-Yue Zhou & Xiao-Bo Liu

  3. Department of Chemistry, the Tsinghua Center for Frontier Polymer Research, Tsinghua University, Beijing, 100084, China

    Liu-Cheng Mao, Jin-Ying Yuan, Lei Tao & Yen Wei

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  1. Zeng-Fang Huang
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  3. Chao-Yue Zhou
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  4. Yan-Hong Li
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  5. Mei Li
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Correspondence to Zeng-Fang Huang or Yen Wei.

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10118_2021_2596_MOESM1_ESM.pdf

Polymerizable AEE-active Dye with Optical Activity for Fluorescent Nanoparticles Based on Phenothiazine: Synthesis, Self-assembly and Biological Imaging

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Huang, ZF., Chen, YL., Zhou, CY. et al. Polymerizable AEE-active Dye with Optical Activity for Fluorescent Nanoparticles Based on Phenothiazine: Synthesis, Self-assembly and Biological Imaging. Chin J Polym Sci 39, 1431–1440 (2021). https://doi.org/10.1007/s10118-021-2596-x

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