0586379 - ÚCHP 2025 RIV US eng J - Journal Article
Kos, Martin - Beránek, Tomáš - Císařová, I. - Cuřínová, Petra - Žádný, Jaroslav - Storch, Jan - Církva, Vladimír - Jakubec, Martin
Resolution of 9,10-Diketo[7]helicene and Its Use in One-StepPreparation of Helicene-Based D−A−D Push−Pull Systems.
Journal of Organic Chemistry. Roč. 89, č. 11 (2024), s. 7495-7502. ISSN 0022-3263. E-ISSN 1520-6904
R&D Projects: GA MV(CZ) VJ01010065
Institutional support: RVO:67985858
Keywords : one hundred years * circularly-polarized luminescence * stereoselective syntheses
OECD category: Organic chemistry
Impact factor: 3.6, year: 2022
Method of publishing: Open access
https://pubs.acs.org/doi/epdf/10.1021/acs.joc.4c00135

Racemic 9,10-diketo[7]helicene was successfullyseparated into enantiomers using a reversible and stereoselectivereaction with 2,2′-diamino-1,1′-binaphthalene with moderateyields but with remarkable purity (>99% de). The enantiomericallypure diketone was used as a convenient starting material for thepreparation of helicene-based push−pull molecules, whichincorporated aza-aryl acceptors and diarylaminophenylene donorgroups in a single step. A series of six push−pull systems, alongwith three reference molecules without donors, were prepared andstudied using UV/vis and fluorescence measurements, circular dichroism, and DFT calculations.
Permanent Link: https://hdl.handle.net/11104/0353919