Journal Articles Advanced Materials Year : 2025

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

Seifallah Abid
Xuesong Li
Delia Miguel
Benoît Champagne
J. Fraser Stoddart

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.

Fichier principal
Vignette du fichier
Advanced Materials - 2025 - García‐Cerezo - Acid Base‐Responsive Circularly Polarized Luminescence Emitters with.pdf (2.37 Mo) Télécharger le fichier
Origin Publication funded by an institution
Licence

Dates and versions

hal-05142748 , version 1 (03-07-2025)

Licence

Identifiers

Cite

Pablo García-Cerezo, Marcos Codesal, Arthur David, Laura Le Bras, Seifallah Abid, et al.. Acid/Base‐Responsive Circularly Polarized Luminescence Emitters with Configurationally Stable Nitrogen Stereogenic Centers. Advanced Materials, 2025, 37, pp.2417326. ⟨10.1002/adma.202417326⟩. ⟨hal-05142748⟩
181 View
86 Download

Altmetric

Share

  • More