Effect of extended conjugation with a phenylethynyl group on the fluorescent properties of water-soluble arylboronic acids

Boronic acids that change fluorescent properties upon sugar binding are very important reporter units for the development of small molecule lectin mimics (boronolectins). Aimed at developing long wavelength fluorescent boronic acid reporter compounds, we have designed and synthesized a series of boronic acid analogs 2a-d with an extended π conjugation. Such designs are based on earlier fluorescent boronic acids that change fluorescent properties upon sugar binding. Compared with the corresponding parent chromophores, these new compounds with extended conjugations show longer excitation and emission wavelengths as designed. The patterns of fluorescent changes for the new compounds are also different from that of the corresponding parent compounds.