Chirality induction of π-conjugated chains through chiral complexation

Abstract

Chirality induction of π-conjugated polyanilines through chiral complexation with the chiral palladium(II) complexes was demonstrated to afford the chiral conjugated polymer complexes. Complexation of the emeraldine base of poly( o-toluidine) (POT) with the chiral palladium(II) complex bearing one labile coordination site led to the formation of the chiral conjugated polymer complex, which exhibited an induced circular dichroism (ICD) based on the chirality induction into a π-conjugated backbone. The mirror image of the CD signal was observed with the chiral conjugated polymer complex, which was obtained from the chiral palladium(II) complex possessing the opposite configuration. The chirality of the podand ligand moieties of the palladium complex is considered to induce a propeller twist of the π-conjugated molecular backbone. The crystal structure of the chiral conjugated complex of N-bis(4′-dimethylaminophenyl)-1,4-benzoquinonediimine (L 3) as a model compound of the polyaniline revealed a chiral propeller twist conformation of the π-conjugated backbone. Furthermore, chiral complexation with the cationic palladium(II) complexes provided the ionic chiral conjugated complexes.