Acid/Base-Responsive Circularly Polarized Luminescence Emitters with Configurationally Stable Nitrogen Stereogenic Centers.

ABSTRACT: A way to prevent the fast configurational interconversion of tertiary amines is to invoke Tröger's base analogs, which display methano- or ethano-bridged diazocine cores fused to aromatic rings. These derivatives are configurationally stable, even in acidic media when their structures bear ethylene bridges. Here, a two- to three-step synthesis is presented of methano- and ethano-bridged Tröger's base analogs with two peripheral fluorophores, i.e., anthracene, pyrene, and 9,9-dimethylfluorene units. These compounds, possessing two nitrogen stereogenic centers, exhibit good circularly polarized luminescence (CPL) dissymmetry factors (|g_lum| up to 1.2 × 10^-3) and brightnesses (B_CPL up to 26.3 M^-1 cm^-1), as well as excellent fluorescence q

SUBMITTER: Garcia-Cerezo P 

PROVIDER: S-EPMC12288784 | biostudies-literature | 2025 Jul

REPOSITORIES: biostudies-literature