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A series of α- and β-ethynyl-substituted BODIPY derivatives ( 3a ,  4a ,  5a, 5b ,  6a, 6b ) were synthesized by gold(I)-catalyzed direct C–H alkynylation reactions of dipyrromethane and BODIPY, respectively, with ethynylbenziodoxolone (EBX) in a regioselective manner. Depending on the position of the ethynyl substituent in the BODIPY skeleton, the photophysical properties of the resulting α- and β-substituted BODIPYs are notably altered. The lowest S 0 –S 1  transition absorbance and fluorescence bands are both bathochromically shifted as the number of substituents increases, while the emission quantum yields of the β-ethynylated derivatives are significantly lower than those of α-ethynylated ones. The current method should be useful for fine-tuning of the photophysical properties of BODIPY dyes as well as for constructing BODIPY-based building cores for functional π-materials.

Regioselectively α- and β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C–H functionalization and their photophysical properties