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Triple Regioselective Functionalization of Cationic [4]Helicenes via Iridium‐Catalyzed Borylation and Suzuki Cross‐Coupling Reactivity

Published inChemistry, vol. 28, no. 56, e202201853
Publication date2022-08-18
First online date2022-08-18
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
  • Ir-catalyzed borylation
  • Late stage functionalization
Research group
Funding
  • Academy of Finland - Bio-orgaanisen kemian ja lääkeainekemian tutkijakoulu [207539]
  • European Commission - Helical systems for chiral organic light emitting diodes [859752]
Citation (ISO format)
FREDERIC, Lucas Dan et al. Triple Regioselective Functionalization of Cationic [4]Helicenes via Iridium‐Catalyzed Borylation and Suzuki Cross‐Coupling Reactivity. In: Chemistry, 2022, vol. 28, n° 56, p. e202201853. doi: 10.1002/chem.202201853
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Article (Published version)
Identifiers
ISSN of the journal0947-6539
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Technical informations

Creation10/11/2022 7:43:00 AM
First validation10/11/2022 7:43:00 AM
Update time03/16/2023 7:59:11 AM
Status update03/16/2023 7:59:10 AM
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