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A switchable red-emitting fluorophore involving a 7.6.6 defect.

Arnab Dutta1,2, Krzysztof Dzieszkowski1, Monika Kijewska3

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A novel macrocyclic derivative with an entangled acridine unit acts as an efficient fluorophore. Its internal cavity and rigid structure enable on/off switching, demonstrating hydrogen-like interactions quench emission in organic chromophores.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Fluorophore Design
  • Photophysics

Background:

  • Macrocyclic compounds offer unique structural control.
  • Acridine derivatives are known for their photoluminescent properties.
  • Controlling fluorescence via external stimuli is crucial for sensor development.

Purpose of the Study:

  • To design and synthesize a novel macrocyclic derivative incorporating an acridine unit.
  • To investigate the photophysical properties of the resulting fluorophore.
  • To explore the mechanism of fluorescence quenching and on/off switching behavior.

Main Methods:

  • Synthesis of a macrocyclic derivative with a 7.6.6 defect structure.
  • Spectroscopic analysis (UV-Vis absorption, fluorescence emission).
  • Computational modeling to understand electronic interactions.

Main Results:

  • The designed molecule exhibits efficient fluorescence.
  • The internal cavity and rigid macrocycle enable tunable optical properties.
  • Hydrogen-like interactions were identified as the primary mechanism for fluorescence quenching, facilitating on/off switching.

Conclusions:

  • Entangling an acridine unit into a rigid macrocycle creates a highly efficient and switchable fluorophore.
  • The unoccupied cavity plays a critical role in modulating photophysical behavior.
  • Hydrogen-like interactions are key to controlling emission in these organic chromophores.