Synthesis and Properties of Water-soluble Glycosyl Fluorescent Polymer with Aggregation-induced Emission Effect†

doi:10.7503/cjcu20170747

Abstract

Abstract:

A glycopolymer{poly[2-(2,3,4,6-four-O-acetyl-α-D-mannopyranose) ethyl methacrylate]-tetraphenylethene}(PAcManEMA-TPE) with defined structure was synthesized by one-pot method, which the reduction of dithioester and Click reaction between thiol and epoxy group were conducted simultaneously. The water-soluble glycopolymer(poly[2-(2,3,4,6-four-O-acetyl-α-D-mannopyranose) ethyl methacrylate]-tetraphenylethene)(PManEMA-TPE) was obtained in a high yield(90%) after the deprotection reaction of PAcManEMA-TPE was carried out. The structure and aggregation-induced emission(AIE) of PManEMA-TPE were characterized by Fourier transform infrared spectrometer, nuclear magnetic resonance spectrometer, gel permeation chromatograph, UV-Vis spectroscopy and photoluminescence. Moreover, the cell toxicity of PManEMA-TPE was assayed by MTT, proving its non-toxicity and showing its potential application as a biomedical probe.

Key words: Tetrapheny ethylene, Water-soluble fluorescent polysaccharide, Aggregation-induced emission effect, Reversible addition-fragmentation chain transfer polymerization

CLC Number:

O636

TrendMD:

LING Yao, LIU Xuejing, HAO Haijing, HAO Xiaohui, BAI Libin, WU Yonggang. Synthesis and Properties of Water-soluble Glycosyl Fluorescent Polymer with Aggregation-induced Emission Effect^†[J]. Chem. J. Chinese Universities, 2018, 39(6): 1319.

Figures/Tables 7

Scheme 1 Mechanism of the “one pot” reaction for the preparation of PManEMA-TPE

Fig.1 1H NMR spectra of PAcManEMA(a) and PAcManEMA-TPE(b) polymer(A) and PManEMA-TPE polymer(B)

Fig.2 FTIR spctra of TPE-2DGE(a), PAcManEMA(b), PAcManEMA-TPE(c) and PManEMA-TPE(d)

Fig.3 GPC chromatograms for PAcManEMA(a) and PAcManEMA-TPE(b)(A) and PManEMA(a), PManEMA-TPE(b) and standard(c)(B)

Fig.4 UV-Vis absorbance spectra of TPE-2DGE(a), PAcManEMA-TPE in H2O/DMSO(99/1)(b) and PManEMA-TPE in H2O/DMSO(1/99)(c)

Fig.5 PL spectra of PAcManEMA-TPE(10 μmol/L) at different volume fractions of water(fw)(A) and different volume fractions of DMSO(fD)(B)Inset in (A): plot of relative PL intensity(F/F0). F is PL intensity at any fw at 460 nm, and F0 is the PL intensity measured at fw=90% at 460 nm. λex=320 nm, slits 5, 5 nm; inset in (B): plot of relative PL intensity(F/F0). F is PL intensity at any fD at 476 nm, and F0 is the PL intensity measured at fD=100% at 476 nm. λex=320 nm, slits 5, 5 nm.

Fig.6 Cell viability of PManEMA-TPE at different concentrationsConcentration/(mg·mL-1): a. 0.005; b. 0.001; c. 0.005; d. 0.10; e. 0.50; f. 1.00.

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