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Superacid-resistant macrocyclic BODIPYs
Keita Watanabe1, Gentaro Honda1, Yuki Terauchi1
1Division of Applied Chemistry, Faculty of Engineering, Hokkaido University, Sapporo, Japan.
Nature Communications
|March 20, 2026
Summary
New macrocyclic Boron-dipyrromethenes (BODIPYs) exhibit exceptional stability in superacids, overcoming fluorescence degradation. These acid-stable BODIPYs enable new applications in harsh chemical environments.
Area of Science:
- Organic Chemistry
- Materials Science
- Analytical Chemistry
Background:
- Boron-dipyrromethenes (BODIPYs) are widely used fluorophores in bioimaging and sensing.
- Conventional BODIPYs suffer from deboronation and fluorescence loss in acidic conditions.
Purpose of the Study:
- To design and synthesize exceptionally acid-stable BODIPYs.
- To investigate their optical properties and stability in strongly acidic media.
- To explore their potential as acid indicators and in materials science.
Main Methods:
- Synthesis of macrocyclic BODIPYs incorporating calix[3]pyrrole-like structures.
- Characterization of optical properties (absorption, emission, quantum yield) in various acidic media.
- Assessment of stability under strongly acidic, thermal, and photolytic stress.
- Demonstration of applications as acid indicators in Nafion beads and sulfonylated gels.
Main Results:
- Macrocyclic BODIPYs demonstrated remarkable stability in superacids, including fluorosulfuric acid, without deboronation.
- These BODIPYs retained fluorescence for over a day in non-diluted fluorosulfuric acid.
- They exhibited sharp absorption, protonation-induced fluorescence switching, high quantum yields (up to 0.90), and narrow Stokes shifts.
- Enhanced thermal and photostability compared to conventional BODIPYs.
- Tunable optical properties via peripheral substitution and fluorous-tagging for specific sensing applications.
Conclusions:
- Macrocyclic BODIPYs offer unprecedented acid resistance, expanding the utility of BODIPY fluorophores.
- These novel compounds are suitable for fluorescence imaging and sensing in strongly acidic, non-aqueous environments.
- Potential applications include advanced materials and challenging biological systems requiring extreme pH stability.
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