Authors
Pablo García-Cerezo, Marcos D Codesal, Arthur H G David, Laura Le Bras, Seifallah Abid, Xuesong Li, Delia Miguel, Masoud Kazem-Rostami, Benoît Champagne, Araceli G Campaña, J Fraser Stoddart, Victor Blanco
Published in
Advanced materials (Deerfield Beach, Fla.). Pages e2417326. May 15, 2025. Epub May 15, 2025.
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 (|glum| up to 1.2 × 10-3) and brightnesses (BCPL up to 26.3 M-1 cm-1), as well as excellent fluorescence quantum yields, demonstrating the Tröger´s base core to be a convenient scaffold to prepare CPL emitters upon functionalization with simple achiral fluorophores. Furthermore, the configurationally stable ethano-bridged Tröger's base analogs are employed to modulate their CPL response, generating a CPL switch through their protonation/deprotonation by consecutive additions of acid and base. The reversibility of the switching process is demonstrated for two cycles without altering the CPL performance of the molecule. It is believed that this straightforward and efficient approach to building CPL emitters employing the Tröger's base core could lead to its incorporation in CPL-based sensors and materials.
PMID:
40371460
Bibliographic data and abstract were imported from PubMed on 15 May 2025.
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