Triple Regioselective Functionalization of Cationic [4]Helicenes via Iridium-Catalyzed Borylation and Suzuki Cross-Coupling Reactivity |
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| Authors: | Dr. Lucas Frédéric Bibiana Fabri Dr. Laure Guénée Dr. Francesco Zinna Prof. Lorenzo Di Bari Prof. Jérôme Lacour |
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| Affiliation: | 1. Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva 4, Switzerland;2. Laboratoire de Cristallographie, University of Geneva, Quai Ernest Ansermet 24, 1211 Geneva 4, Switzerland;3. Dipartimento di Chimica e Chimica Industriale, University of Pisa, Via G. Moruzzi 13, Pisa, Italy |
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| Abstract: | In essentially one-pot, using Ir- and Pd-catalysis, tris(arene)-functionalized cationic [4]helicenes are synthesized with full regioselectivity and enantiospecificity starting from a trivial precursor (17 examples). This poly-addition of aryl groups improves key optical properties, that is, fluorescence quantum yields and lifetimes. Electronic circular dichroism and circularly polarized luminescence signatures are observed up to the far-red domain, in particular with additional arenes prone to aggregation. |
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| Keywords: | cationic helicenes chiroptical spectroscopy dyes and fluorophores Ir-catalyzed borylation •late stage functionalization |
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