Tuning Molecular Rigidity with Seven-Membered Ring Fusion: A Strategy toward Bright Near-Infrared azaBODIPY Fluorophores
Abstract
A streamlined synthesis of structurally unprecedented, seven-membered-ring-fused azaBODIPYs has been developed. Single-crystal X-ray analysis and calculations for this seven-membered-ring-fused azaBODIPY revealed severely twisted 1,3,5,7-aryl substituents. The twisted, rigidified structure dramatically enhances photophysical performance. Suppressing internal conversion yields bright near-infrared fluorescence (molar extinction coefficient ε up to 1.3 × 10 5 M –1 cm –1 and fluorescence quantum yield Φ F up to 74.2%). For a derivative bearing 1,7-dithiophenes, rapid intersystem crossing instead leads to efficient reactive oxygen species generation (Φ Δ = 28% in toluene), demonstrating its potential applications as a photosensitizer.
Fields of Study & Subjects
Luminescence and Fluorescent Materials
Nanoplatforms for cancer theranostics
Molecular Sensors and Ion Detection
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 20
- Pages
- 6427–6432
- Publication date
- 8 May 2026
- Language
- EN