Merging Triptycene, BODIPY and Porphyrin Chemistry: Synthesis and Properties of Mono- and Trisubstituted Triptycene Dye Arrays
| Autor: | Ganapathi Emandi, Mathias O. Senge, Yasser M. Shaker, Keith J. Flanagan, Jessica M. O'Brien |
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| Rok vydání: | 2017 |
| Předmět: |
010405 organic chemistry
Organic Chemistry Sonogashira coupling Crystal structure 010402 general chemistry Electrochemistry 01 natural sciences Combinatorial chemistry Fluorescence Porphyrin 0104 chemical sciences chemistry.chemical_compound chemistry Triptycene Organic chemistry Physical and Theoretical Chemistry BODIPY Conjugate |
| Zdroj: | European Journal of Organic Chemistry. 2017:6680-6692 |
| ISSN: | 1434-193X |
| Popis: | A series of functionalized triptycene scaffolds has been synthesized using 2-formyltriptycene and 5-(2-triptycenyl)dipyrromethane. Using these two key precursors, mixed condensations with different aromatic aldehydes and aryl-dipyrromethanes gave access to all members of triptycenyl meso-substituted porphyrins (AB3-, A2B2-, A3B-, and A4) and allowed their photophysical and electrochemical characterization. Additionally, the first crystal structure of tetratriptycenylporphyrin is reported. 2-Formyltriptycene was also used for the preparation of two different mono-BODIPY-triptycene compounds, while 2,6,14-triiodotriptycene was used in Suzuki and Sonogashira cross-coupling reactions to obtain three-fold BODIPY-substituted triptycene-dye conjugates. The mono- and tri-BODIPY-substituted triptycene scaffolds exhibit good optical properties in the visible to NIR region indicating the potential use of the triptycene scaffold as the core of multi-dye light-harvesting system |
| Databáze: | OpenAIRE |
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