Hexabenzoheptacene: A Longitudinally Multihelicene Nanocarbon with Local Aromaticity and Enhanced Stability.
Angew Chem Int Ed Engl
; 63(29): e202407547, 2024 Jul 15.
Article
en En
| MEDLINE
| ID: mdl-38725308
ABSTRACT
We report the synthesis of a longitudinally helical molecular nanocarbon, hexabenzoheptacene (HBH), along with its dimethylated derivative (HBH-Me), which are composed of six benzene rings periodically benzannulated to both zigzag edges of a heptacene core. This benzannulation pattern endows the resulting nanocarbons with a helical heptacene core and local aromaticity, imparting enhanced solubility and stability to the system. The chiral HBH-Me adopts a more highly twisted conformation with an end-to-end twist angle of 95°, enabling the separation of the enantiomers. Both HBH and HBH-Me can be facilely oxidized into their corresponding dications, which exhibit enhanced planarity and aromaticity upon loss of electrons. Notably, both longitudinally helical nanocarbons readily promote solid state packing into two-dimensional (2D) arrangement. Single-crystal microbelts of HBH-Me show hole mobility up to 0.62â
cm2 V-1 s-1, illustrating the promising potential of these longitudinally helical molecules for organic electronic devices.
Texto completo:
1
Banco de datos:
MEDLINE
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Año:
2024
Tipo del documento:
Article