(BO)₂ -Doped Tetrathia[7]helicene: A Configurationally Stable Blue Emitter.

ABSTRACT: Helicenes combine two central themes in chemistry: extended π-conjugation and chirality. Hetero-atom doping preserves both characteristics and allows modulation of the electronic structure of a helicene. Herein, we report the (BO)₂ -doped tetrathia[7]helicene 1, which was prepared from 2-methoxy-3,3'-bithiophene in four steps. 1 is formally derived by substituting two (Mes)B-O moieties in place of (H)C=C(H) fragments in two benzene rings of the parent tetrathia[7]helicene. X-ray crystallography revealed a dihedral angle of 50.26(9)° between the two terminal thiophene rings. The (P)-/(M)-1 enantiomers were separated by chiral HPLC and are configurationally stable at room temperature. The experimentally determined enantiomerization barrier of 27.4±0.1 kcal mol^-1 is lowe

SUBMITTER: Menduti L 

PROVIDER: S-EPMC10107351 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature