Cyclobishelicenes: Shape-Persistent Figure-Eight Aromatic Molecules with Promising Chiroptical Properties
- Resource Type
- Authors
- Michel Giorgi; Yoann Coquerel; Harald Bock; Emilie Pouget; Yannick Carissan; Christie Aroulanda; Antoine Scalabre; Antoine Robert; Fabien Durola; Nicolas Vanthuyne; Marion Jean; Guillaume Naulet
- Source
- Chemistry-A European Journal
Chemistry-A European Journal, Wiley-VCH Verlag, 2019, 25 (63), pp.14364-14369
Chemistry-A European Journal, 2019, 25 (63), pp.14364-14369. ⟨10.1002/chem.201902637⟩
Chemistry-A European Journal, Wiley-VCH Verlag, 2019, 25 (63), pp.14364-14369. ⟨10.1002/chem.201902637⟩
- Subject
- 010405 organic chemistry
Chemistry
aromatic compounds
Organic Chemistry
chirality
chiroptical properties
General Chemistry
[CHIM.MATE]Chemical Sciences/Material chemistry
010402 general chemistry
Inherent chirality
01 natural sciences
Catalysis
0104 chemical sciences
[CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry
Crystallography
chemistry.chemical_compound
Helicene
helical structures
conformation analysis
Molecule
Enantiomer
Chirality (chemistry)
Conformational isomerism
- Language
- English
- ISSN
- 0947-6539
1521-3765
International audience; Cyclobis[n]helicenes (n = 3 or 5) are chiral D2-symmetric p-conjugated macrocycles with stable lemniscular, or figure-eight, shapes. The conformational analysis of five different cyclobis[n]helicenes revealed that these molecules can only exist as their lemniscular conformers with high barriers to enantiomerization (>200 kJ.mol-1). The enantiomers of a cyclobis[5]helicene were resolved by HPLC and their unusual chiroptical properties were attributed to the inherent chirality of their macrocyclic figure-eight.