Synthesis and aggregation-induced emission of a pyrene decorated chiral BODIPY chromophore

•This is the first report on 2,6-disubstituted pyrene-terminated BODIPY dye.•The BODIPY chromophore possesses emission maximum at 585 nm.•This material shows a strong orange fluorescence peak with the high quantum yield.•The photophysical behavior in the aggregated state was also investigated.

BODIPY chromophore with pyrene moieties was designed and synthesized successfully in the present paper. Optical results demonstrate that the pyrene-terminated dye 3 presents a bigger Stokes shift and slightly smaller fluorescence quantum yield in the red region than BODIPY dye 1 bearing no substituent at 2,6-positions. Dye 3 possesses absorption and emission maximum at 530 and 585 nm in THF solution, respectively. With the addition of different water volume fractions, the gradually bathochromic shifts are observed in the absorption and emission spectra, simultaneously. Under UV irradiation, the corresponding emission images of solutions/aggregates are visual, showing the aggregation-caused quenching effect of orange fluorescence. In addition, theoretic computational studies on related pyrene decorated chiral BODIPY compounds have also been carried out.

Graphical abstractThe first 2,6-disubstituted pyrene-terminated BODIPY dye is reported. This material presents a strong orange fluorescence peak with the high quantum yield. With the addition of different water volume fractions, the gradually bathochromic shifts are observed in the absorption and emission spectra, simultaneously.Figure optionsDownload full-size imageDownload as PowerPoint slide