Abstract
A selective method for the core-extension of boron dipyrromethene (BODIPY) with two annulated indole rings with exclusive syn-connectivity is reported. The method is based on a regioselective nucleophilic substitution reaction of 2,3,5,6-tetrabromoBODIPY with aryl amines, followed by palladium-catalyzed intramolecular C-C coupling ring fusion. The unsymmetrical core-expanded BODIPY with annulated indole and benzofuran rings was also synthesized by stepwise and regioselective nucleophilic substitution and palladium-catalyzed intramolecular C-C coupling reaction. The diindole-annulated BODIPY was unambiguously characterized by single-crystal X-ray analysis. The optical properties of the present core-expanded BODIPYs were studied, revealing clearly red-shifted absorption and emission bands and enhanced absorption coefficients upon annulation.
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