A new family of pyrrolyl–acylhydrazones anchored with two BF2 units, named BOAPY, have been developed as BODIPY-like and unsymmetrical bis­(BF2) chromophores via a simple one-pot reaction. The easily accessible scaffold enjoys excellent diversity due to the structural versatilities of 2-formylpyrroles and acylhydrazines. BOAPYs exhibit good molar absorption coefficients, large Stokes shifts, and excellent chemical stability. More importantly, most of them display excellent fluorescence quantum yields both in solution and the solid state (up to 0.88 and 0.64, respectively).

We have synthesized the near-infrared watersoluble conjugated polymer poly[2,5-di(propyloxysulfonate)-1,4-phenylene-ethynylene-9,10-anthrylene (referred to as PPEASO3). Its fluorescence (at wavelengths between 650 and 800 nm following photoexcitation at 550 nm) is efficiently quenched by Cu(II) ions, while other physiologically relevant metal ions do not cause significant quenching at the same concentrations. Under optimum conditions, fluorescence intensity is inversely proportional to the concentration of Cu (II). The calibration curve displays two linear regions over the range of 0-3.2×10 −7 mol L −1 and 3.2×10 −7 mol L −1 to 1.0× 10 −4 mol L −1 of Cu(II), respectively. The long-wavelength excitation and emission can substantially reduce interferences by the autofluorescence and light scattering of biological matter under UV excitation. The method was successfully applied to the determination of Cu(II) in synthetic and tea samples.

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 bisBF 2 -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 paradimethylaminophenyl 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.

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