Dapoxyl dyes are ideally suited for applications in luminescence-based sensing, exhibiting environment-sensitivity that surpasses other commercially available luminophores. Specifically, a dramatic shift in emission wavelength is observed upon variation of solvent polarity. However, the inability to covalently link the sensor molecule to other species hinders the progress of sensing method development. Accordingly, a Dapoxyl derivative is envisioned that is easily functionalized for further manipulations. The proposed synthesis is convergent to yield a 2,5-disubstituted oxazole and is highly versatile, in that functionalization of the derivative occurs in the final transformation. An acrylamido derivative of the luminophore will be utilized in the development of luminescence-based sensors for the measurement of analytes in both vapor and aqueous phase. Reported here are the proof of principle of the sensing strategy, progress toward synthesis of the luminophore, and broader implications in the development of luminescence-based sensing methods.

Synthesis of Dapoxyl derivatives for applications in luminescence-based sensing

243rd National Meeting (2012)

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