Helquat-induced chiroselective aggregation of Au NPs.

Abstract

Au nanoparticles (NPs) are functionalized with chiral (R) or (S) binaphthol phenylboronic acid ligands, (1a) or (1b). The (R)- or (S)-binaphthol phenylboronic acid ligands form donor-acceptor complexes with the chiral dicationic helicene, helquat (P)-HQ(2+) or (M)-HQ(2+), (2a) or (2b). The association constants between (1a)/(2a) and (1a)/(2b) correspond to (7.0 ± 0.5) × 10(5) M(-1) and (2.5 ± 0.3) × 10(5) M(-1), respectively, whereas the association constants between (1b)/(2b) and (1b)/(2a) correspond to (4.0 ± 0.5) × 10(5) M(-1) and (1.8 ± 0.3) × 10(5) M(-1), respectively. Chiroselective aggregation of chiral binaphthol phenylboronic acid-capped Au NPs triggered by the chiral helquats, is demonstrated.