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- Title
Synthesis of a Double Helicene by a Palladium-Catalyzed Cross-Coupling Reaction: Structure and Physical Properties.
- Authors
Kashihara, Hitoshi; Asada, Toshio; Kamikawa, Ken
- Abstract
For this study, twisted π-extended helicene 1 and double helicene 2 with a helicene framework were synthesized through palladium-catalyzed CH arylation or Suzuki-Miyaura coupling reaction. X-ray crystallography revealed grossly twisted structures that were soluble in various conventional organic solvents. Optical properties based on UV/Vis and fluorescence spectra were measured. Electrochemical properties were also studied by measurements of cyclic voltammetry in 1 and 2, which revealed their HOMO and the LUMO energies. Theoretical calculation supports their HOMO and LUMO energies and molecular orbitals. Furthermore, a racemization process of 2 predicted that the activation free energy at 300 K would be 31.8 kcal mol−1 by DFT calculation, which indicated the static helicity at 300 K.
- Subjects
HELICENES; AROMATIC compound synthesis; PALLADIUM catalysts; CARBON-hydrogen bonds; ARYLATION; SUZUKI reaction; CRYSTALLOGRAPHY
- Publication
Chemistry - A European Journal, 2015, Vol 21, Issue 17, p6523
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201500074