5 years ago

10-Silacorroles Exhibiting Near-Infrared Absorption and Emission

10-Silacorroles Exhibiting Near-Infrared Absorption and Emission
Hiroto Omori, Hiroshi Shinokubo, Satoru Hiroto
10-Silacorroles were obtained from the Pd-catalyzed silylative cyclization of a bis(α,α′-dibromodipyrrin) NiII precursor with dihydrosilanes. These 10-silacorroles show substantially red-shifted absorption bands relative to those of normal porphyrins and isocorroles. Notably, the corresponding free base and ZnII 10-silacorroles exhibit emissions in the NIR region. Theoretical calculations on these 10-silacorroles revealed the presence of σ*–π* conjugation between the silyl group and the tetrapyrrole π system, which significantly lowers their LUMO energy levels. Jump to 1000 nm! A new family of heteroporphyrinoid, 10-silacorroles, has been prepared through Pd-catalyzed silylation of a dibromodipyrrin NiII precursor. 10-Silacorroles exhibited near-infrared absorption (NIR) and emission. Theoretical analysis and electrochemical investigation revealed the presence of σ*–π* conjugation between the silicon atom and tetrapyrrolic macrocyclic skeleton.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701474

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