Tandem Regioselective Substitution and Palladium‐Catalyzed Ring Fusion Reaction for Core‐Expanded Boron Dipyrromethenes with Red‐Shifted Absorption and Intense Fluorescence |
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| Authors: | Xin Zhou Qinghua Wu Yuanmei Feng Yang Yu Changjiang Yu Prof?Dr Erhong Hao Yun Wei Xiaolong Mu Prof?Dr Lijuan Jiao |
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| Institution: | The Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, China |
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| 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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| Keywords: | BODIPY dipyrromethene dyes/pigments intramolecular arylation regioselectivity |
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