A Family of Highly Fluorescent and Membrane-Permeable Bis(BF2) Acyl-Pyridinylhydrazine Dyes with Strong Solid-State Emission and Large Stokes Shifts: The BOAPH Fluorophores.

ABSTRACT

Organic small-molecule fluorescent chromophores have become essential to modern chemical, biological, and materials related investigations. Herein, a straightforward synthesis and subsequent borylation were presented to form a novel family of bisBF2-anchoring acyl-pyridinylhydrazine, which we named BOAPH. The chromophore enjoys outstanding structural diversities owing to varied acyl chlorides and N-heteroarenylhydrazides. These resultant BOAPH dyes are confirmed by NMR, HRMS, and single-crystal X-ray structure analysis. Their spectroscopic properties were studied, and most of the strong absorbance and bright fluorescence with maximum wavelengths centered in the range of 400 and 650 nm. More importantly, they exhibit promising fluorescence quantum yields up to 0.79 in solution and solid states, good photostability, and large Stokes shifts. Furthermore, a respective BOAPH dye with a para-dimethylaminophenyl group exhibited the interesting ability of ultrafast staining and two-photon imaging, which can specifically label lipid droplets of living cells immediately without the need for incubation.