Self-Assembly and Circularly Polarized Luminescence from Achiral Pyrene-Adamantane Conjugates by Selective Inclusion with Cyclodextrins.

The interaction between guest chromophores or lumiphores with host chiral cavity and their induced chirality is an important topic in supramolecular chemistry. Kodaka and Harata proposed a rule to explain the induced circular dichroism of the guest chromophores by host cyclodextrins. However, it remains unknown how a circularly polarized luminescence (CPL) signal will change when the lumiphores interacted with cyclodextrins in different modes. Here, we designed an achiral pyrene-adamantane conjugated guest molecule, N-(pyren-1-yl)adamantane-1-carboxamide (ACNP), and investigated its interactions with α/β/γ-cyclodextrins (CDs) and its induced CPL. Depending on the size match of the pyrene, adamantine with different cyclodextrins, distinct performance was observed. While α-CD could not induce a CPL signal of ACNP, β-CD could induce CPL in two modes, through adamantyl or direct pyrenyl induction, which could produce a CPL signal with opposite signs. γ-CD could always induce a negative CPL signal. Therefore, a rule of induced CPL of lumiphores by cyclodextrins can be proposed.