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Coumarin-Based Boron Complexes with Aggregation-Induced Emission.

Panpan Zhang1,2, Weimin Liu2,3, Guangle Niu2

  • 1Institute of Functional Nano & Soft Materials (FUNSOM), Collaborative Innovation Center of Suzhou Nano Science and Technology, Jiangsu Key Laboratory for Carbon-Based Functional Materials & Devices, Soochow University , Suzhou 215123, China.

The Journal of Organic Chemistry
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Two novel boron complexes exhibit aggregation-induced emission, showing enhanced fluorescence in specific solvents and solid states. These coumarin-based compounds demonstrate potential as bright red emitters and lysosome trackers in cell imaging.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photophysics

Background:

  • Aggregation-induced emission (AIE) is a phenomenon where molecules exhibit enhanced fluorescence upon aggregation.
  • Coumarin derivatives are widely studied for their photophysical properties.
  • Boron complexes offer unique electronic and structural characteristics.

Purpose of the Study:

  • To design and synthesize novel coumarin-based boron complexes with aggregation-induced emission (AIE) properties.
  • To investigate the photophysical behavior of these complexes in various environments.
  • To explore their potential applications in cell imaging.

Main Methods:

  • Synthesis of two coumarin-based boron complexes, HBN and MBN.
  • Photophysical characterization in different solvents (e.g., THF, acetonitrile/water mixtures).
  • Solid-state emission analysis.
  • Cell-imaging experiments to assess membrane permeability and lysosome tracking capabilities.

Main Results:

  • The N,O-chelated BF2 moiety inhibited C═N isomerization, leading to significant fluorescence enhancement in THF.
  • Red-shifted emissions (>60 nm) were observed in acetonitrile/water mixtures due to aggregation-induced charge-transfer enhancement.
  • Bright red emission at 650 nm (620 nm) with a large Stokes shift of 170 nm was achieved in the solid state.
  • The complexes demonstrated good membrane permeability and effective lysosome tracking in cell imaging.

Conclusions:

  • The designed coumarin-based boron complexes exhibit promising AIE characteristics.
  • Inhibited isomerization and aggregation-induced charge-transfer are key factors for enhanced fluorescence.
  • These complexes show potential as solid-state red emitters and as fluorescent probes for lysosome imaging.