Abstract
This article describes a new block copolymer (EGm-b-APn, where m and n denote the degrees of polymerization) of poly(ethylene glycol) (PEG) and poly(1,4-(1-H-1,2,3-triazolylene)methylene) prepared by copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) polymerization of 3-azido-1-propyne (AP) in the presence of PEG carrying a propargyl moiety. The EGm-b-APn samples are well soluble in polar organic solvents. Unexpectedly, we observed that solutions of EGm-b-APn in N,N-dimethylformamide emitted fluorescence. We systematically studied absorption and emission properties of the block copolymers. The experimental data have exhibited that APn block is an intrinsic fluorophore. Interestingly, the emission of EGm-b-APn can be easily tuned from ultraviolet to green fluorescence by changing the excitation wavelength. This enables fine-tuning of its optical property without the need of changing the chromophore. Moreover, the block copolymers show a fluorescence response to metal ions (e.g., Cu2+). Our discoveries contribute to the fundamental understanding of the optical properties of dense triazole-based polymer and raise intriguing prospects for fabricating novel emissive triazole-based materials.
Highlights
This article describes a new block copolymer (EGm-b-APn, where m and n denote the degrees of polymerization) of poly(ethylene glycol) (PEG) and poly(1,4-(1-H-1,2,3-triazolylene)methylene) prepared by copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) polymerization of 3-azido1-propyne (AP) in the presence of PEG carrying a propargyl moiety
We have synthesized a diblock copolymer (EGm-b-APn, m and n denote the degrees of polymerization (DP)) of poly(ethylene glycol) (PEG) and dense 1,2,3-triazole blocks to investigate the properties of AP oligomer in solution
NMR spectra were recorded on a JEOL JNM ECA500 spectrometer using CDCl3 or dimethyl sulfoxide-d6 (DMSO-d6 ) as a solvent
Summary
1,2,3-Triazole is an intriguing nitrogen-rich aromatic heterocycle possessing a large dipole moment [1,2,3]. 1,2,3-Triazoles are formed from azides and alkynes by Huisgen cycloaddition [4,5], one of. The dense 1,2,3-triazole oligomers were insoluble in common organic solvents presumably because of strong dipole–dipole interaction, they were well soluble in strong acids (e.g., concentrated sulfuric acid, nitric acid, and hydrochloric acid). This observation indicates that protonation makes the oligomers soluble. We have synthesized a diblock copolymer (EGm-b-APn, m and n denote the degrees of polymerization (DP)) of poly(ethylene glycol) (PEG) and dense 1,2,3-triazole blocks to investigate the properties of AP oligomer in solution. We have further examined the fluorescence behavior of EGm-b-APn responsive to external stimuli (i.e., metal ions)
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