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Thiazole Boron Difluoride Dyes with Large Stokes Shift, Solid State Emission and Room-Temperature Phosphorescence
Wei Wang1,2, Shuo Tong3, Qi-Qiang Wang1,2
1Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, P. R. China.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 22, 2022
Summary
New boron-dipyrromethene (BODIPY) dyes overcome solid-state emission limits. These novel fluorophores exhibit large Stokes shifts and enhanced luminescence, with some showing dual fluorescence and room-temperature phosphorescence.
Area of Science:
- Organic Chemistry
- Materials Science
- Photophysics
Background:
- Boron-dipyrromethene (BODIPY) dyes suffer from small Stokes shifts and weak solid-state emission.
- Developing new fluorophores with improved photophysical properties is crucial for advanced applications.
Purpose of the Study:
- To design, synthesize, and characterize novel boron difluoro complexes based on thiazole scaffolds.
- To investigate the luminescent properties, including Stokes shift, quantum yield, and solid-state emission, of these new dyes.
- To explore dual fluorescence and room-temperature phosphorescence (RTP) capabilities.
Main Methods:
- Chemical synthesis of novel boron difluoro complexes.
- Spectroscopic analysis (UV-Vis absorption, fluorescence emission) in solution and solid state.
- X-ray crystallography to determine molecular structure and intermolecular interactions.
- Time-resolved luminescence measurements for phosphorescence lifetime.
Main Results:
- Synthesized thiazole-based boron difluoro complexes with large Stokes shifts (77-101 nm).
- Achieved high fluorescence quantum yields (up to 64.9% in solution, 34.7% in solid state).
- Observed dual fluorescence and RTP in some compounds, with tunable phosphorescence quantum yields and lifetimes up to 251 μs.
- X-ray structures indicated intramolecular H-bonds and minimal π-π stacking, correlating with large Stokes shifts and solid-state emission.
- Iodine incorporation and specific intermolecular interactions (halogen bonding, π-π, C-H···π) were linked to RTP.
Conclusions:
- The designed thiazole-based BODIPY analogues effectively address the limitations of traditional BODIPY dyes.
- These novel fluorophores demonstrate significant potential for applications requiring strong solid-state emission and advanced photophysical properties like RTP.
- Molecular design strategies involving intramolecular hydrogen bonding and controlled intermolecular interactions are key to enhancing luminescence and achieving RTP.
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