Functionalization of Poly(divinylbenzene) Microspheres by Combination of Hydrobromination and Click Chemistry Processes: A Model Study

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 NaN3 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. (C) Koninklijke Brill NV, Leiden, 2009