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Superacid-resistant macrocyclic BODIPYs.

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New macrocyclic Boron-dipyrromethenes (BODIPYs) exhibit exceptional stability in superacids, overcoming fluorescence degradation. These acid-stable BODIPYs enable new applications in harsh chemical environments.

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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.