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

Zeng-Fang Huang; Ya-Li Chen; Chao-Yue Zhou; Yan-Hong Li; Mei Li; Xiao-Bo Liu; Liu-Cheng Mao; Jin-Ying Yuan; Lei Tao; Yen Wei

doi:10.1007/s10118-021-2596-x

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

ARTICLE | Updated：2021-07-08

- Polymerizable AEE-active Dye with Optical Activity for Fluorescent Nanoparticles Based on Phenothiazine: Synthesis, Self-assembly and Biological Imaging
- Polymerizable AEE-active Dye with Optical Activity for Fluorescent Nanoparticles Based on Phenothiazine: Synthesis, Self-assembly and Biological Imaging
- Chinese Journal of Polymer Science 2021年39卷第11期页码：1431-1440
- Affiliations：
  
  a.School of Materials & Food Engineering, Zhongshan Institute, University of Electronic Science & Technology of China, Zhongshan 528402, China
  b.School of Materials and Energy, University of Electronic Science & Technology of China, Chengdu 610054, China
  c.Department of Chemistry, the Tsinghua Center for Frontier Polymer Research, Tsinghua University, Beijing 100084, China
- Author bio：
  
  hzf105@163.com (Z.F.H.)
  weiyen@tsinghua.edu.cn (Y.W.)
- Funds：
  
  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).
- DOI：10.1007/s10118-021-2596-x
  中图分类号：
- 收稿：2021-02-09，
  
  修回：2021-4-9，
  
  录用：2021-4-20，
  
  网络首发：2021-07-08，
  
  纸质出版：2021-09-18
- Accepted：
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Huang, Z. F.; Chen, Y. L.; Zhou, C. Y.; Li, Y. H.; Li, M.; Liu, X. B.; Mao, L. C.; Yuan, J. Y.; Tao, L.; Wei, Y. Polymerizable AEE-active dye with optical activity for fluorescent nanoparticles based on phenothiazine: synthesis, self-assembly and biological imaging. Chinese J. Polym. Sci. 2021, 39, 1431–1440

Zeng-Fang Huang, Ya-Li Chen, Chao-Yue Zhou, et al. Polymerizable AEE-active Dye with Optical Activity for Fluorescent Nanoparticles Based on Phenothiazine: Synthesis, Self-assembly and Biological Imaging[J]. Chinese Journal of Polymer Science, 2021, 39(11): 1431-1440.
Huang, Z. F.; Chen, Y. L.; Zhou, C. Y.; Li, Y. H.; Li, M.; Liu, X. B.; Mao, L. C.; Yuan, J. Y.; Tao, L.; Wei, Y. Polymerizable AEE-active dye with optical activity for fluorescent nanoparticles based on phenothiazine: synthesis, self-assembly and biological imaging. Chinese J. Polym. Sci. 2021, 39, 1431–1440 DOI： 10.1007/s10118-021-2596-x.

Zeng-Fang Huang, Ya-Li Chen, Chao-Yue Zhou, et al. Polymerizable AEE-active Dye with Optical Activity for Fluorescent Nanoparticles Based on Phenothiazine: Synthesis, Self-assembly and Biological Imaging[J]. Chinese Journal of Polymer Science, 2021, 39(11): 1431-1440. DOI： 10.1007/s10118-021-2596-x.

摘要

Abstract

In consideration of various advantages such as less harm

higher sensitivity

and deeper imaging depth

etc.

AIE materials with long-wave 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 (

)-PVHMA monomer with chirality and aggregation-induced emission enhancement (AEE) characteristics was acquired through enzymatic transesterification reaction basing on phenothiazine

and its

$${\left[\alpha \right]}_{D}^{25^\circ {\rm{C}}}$$

http://notExist.jpg

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 (

)-PVHMA and PEGMA with various feed ratios. When the feed molar ratio of (

)-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 2.2×10

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 nano-particles. In a 90% water solution of H

O 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.

关键词

Keywords

references

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