Rylene dyes have been shown to be useful as fluorescent sensors due to their low native fluorescence and their stability in a range of environments. However, their insolubility in water severely limits the scope of their function. In this study we have synthesized and characterized a series of rylene dye derivatives that incorporate different polar groups in an attempt to improve the solubility of the sensor while maintaining its fluorescence. The synthetic path we’ve chosen creates three stable products, each of which having unique functional groups for analysis. It begins by the conjugation of 2-nitrophenol and 4-bromo-1,8-naphthalic anhydride using an Ullman-type reaction, followed by a reduction under inert atmosphere using tin (II) chloride to yield the corresponding amine, and finished with a Pschorr ring-closing reaction to form a xanthene derivative. Initial spectroscopic analysis of the products has shown that the molecules have adequate water solubility, as well as indicating significant changes in the emission intensity with different substituents.

Synthesis and spectroscopic characterization of naphthalic anhydride derivatives

255th National Meeting (2018)

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