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
- Chinese Journal of Polymer Science Vol. 39, Issue 11, Pages: 1431-1440(2021)
- 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：
- DOI：10.1007/s10118-021-2596-x
  CLC：
- Received：09 February 2021，
  
  Revised：2021-4-9，
  
  Accepted：20 April 2021，
  
  Online First：08 July 2021，
  
  Published：18 September 2021
- 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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