Highly Fluorescent Sensing of Nitroaromatic Explosives in Aqueous Media using Pyrene-Linked PBEMA Microspheres



Hamza Turhan, Ece Tukenmez, Bunyamin Karagoz, Niyazi Bicak


Crosslinked 2-bromoethyl methacrylate polymer (PBEMA) was prepared in micro-spherical form (2–5 µm) by precipitation polymerization methodology. The bromide substituent was substituted with an azide group, which was then coupled with 1-[(2-Propynyloxy)methyl]pyrene] via alkyne-azide click chemistry. The pyrene-linked microspheres showed an intense green-blue excimer emission with a maximum at 480 nm, implying π−π stacking between the pyrene moieties on the microsphere surfaces. This fluorescence emission is extremely sensitive to the aromatic nitro compounds. So that the green-blue light fades immediately upon addition of trace amounts of 2,4,6-trinitrotoluene (TNT), 2,4-dinitrotoluene (DNT) and 2,4,6-trinitro phenol (TNP) in 100% aqueous media. Stern-Volmer plots were employed for comparison of their fluorescence quenching effects. The plots revealed Stern-Volmer constants of 1.33 × 105, 2.451 × 105 and 1.076 × 105 M−1 for TNT, TNP and DNT, respectively. Furthermore, it has been observed that, the microspheres can be reused several times, without losing excimer emission properties.

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