Side-chain pyrene functional poly(vinyl alcohol) (PVA) was synthesized by using ''click chemistry'' strategy. First, partial tosylation of PVA with p-toluene sulfonyl chloride were performed. The resulting PVA-Ts polymer was then quantitatively converted into poly(vinyl alcohol)-azide (PVA-N 3 ) in the presence of NaN 3 /DMF at 60 C. Propargyl pyrene was prepared independently as a photoactive click component. Finally, azido functionalized PVA was coupled to propargyl pyrene with high efficiency by click chemistry. Incorporation of pyrene functionality in the resulting polymer was confirmed by spectral analysis. It is also shown that pyrene functionalized PVA (PVA-Py) exhibited characteristic fluorescence properties and improved solubility in highly polar solvents such as water, DMSO, and DMF as well as less polar solvent such as THF compared with pristine PVA. V
Poly(vinyl alcohol)-pyrene-glucose oxidase (PVA-Py-GOx), a water-soluble polymer possessing both fluorescent and oxidant sites in the structure, is synthesized by "click" chemistry and modification processes and characterized. The morphology of PVA-Py-GOx was characterized with atomic force microscopy (AFM), and a heterogeneous morphology due to the incorporation of GOx was observed. The capability of PVA-Py-GOx to act as a bioprobe for fluorescence sensing of glucose is examined. The postulated fluorescence mechanism for glucose analysis is based on the consumption of glucose by dissolved oxygen and GOx present in the structure. Thus, the fluorescence intensity of pyrene groups of the probe increases by the elimination of fluorescence quenching by oxygen. Glucose concentration was analyzed quantitatively from 0.25 to 3.0 mM by the fluorescence measurement. The effect of pH and amount of PVA-Py-GOx was also studied. The proposed system was applied to analyze glucose in real samples and compared with those obtained from commercial kits.
Fluorescent pyrene-functional poly(divinylbenzene) (PDVB) cross-linked core microspheres were synthesized using the click chemistry strategy as a model study. First, the core monodisperse microspheres were prepared by precipitation polymerization using 2,2 -azobisisobutronitrile (AIBN) as initiator in acetonitrile in the absence of any stabilizer. Residual double bonds were converted to azide-functions by hydrobrominated with hydrogen bromide followed by azidation with NaN 3 in DMF solution. Propargyl pyrene was prepared independently as a fluorescent click component. Finally, azide-functionalized microspeheres were coupled with propargyl pyrene with high efficiency by click chemistry. The modified PDVB microspheres are characterized by using FT-IR spectroscopy, UV-Vis absorption spectroscopy, fluorescence spectroscopy and fluorescence microscopy.
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