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Updated: May 15, 2025

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Dipyrroethene-Based Red-Light Emissive AIEgens.

Debasish Mandal1, Saugat Mondal2, Abani Sarkar1

  • 1Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.

ACS Applied Materials & Interfaces
|April 8, 2025
PubMed
Summary
This summary is machine-generated.

Researchers developed new red-light emitting aggregation-induced emission (AIE) molecules based on the E-dipyrroethene skeleton. These novel AIEgens offer tunable photophysical properties and enhanced fluorescence for sensing and bioimaging applications.

Keywords:
Red-light emissive AIEgenlive cell imagingpH-responsive AIEgensupramolecular chemistryvapochromism

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Photophysics

Background:

  • Aggregation-induced emission (AIE) molecules are crucial for applications like biomedical probes, chemical sensors, and optoelectronics.
  • Tetraphenylethene (TPE) derivatives are benchmark AIE materials but have limitations in tunability and emission range.
  • Existing AIE materials often have absorption and emission in higher-energy regions, restricting their use.

Purpose of the Study:

  • To design and synthesize novel, highly symmetric, red-light emissive AIE-active molecules.
  • To overcome the limitations of TPE derivatives by enabling tunable photophysical properties.
  • To explore new AIEgens for advanced applications in sensing and bioimaging.

Main Methods:

  • Structural engineering of the E-dipyrroethene (DPE) skeleton to create new AIEgens.
  • Synthesis of DPE-based AIEgens (Tz and BTz) via α,α-diformylation and condensation reactions.
  • Comprehensive characterization including experimental, spectroscopic, theoretical studies, and X-ray crystallography.

Main Results:

  • Synthesized DPE-based AIEgens (Tz and BTz) with π-extended conjugation and multiple heteroatoms.
  • Achieved visible excitation and emission spectra above 600 nm with large Stokes shifts (3632-5058 cm⁻¹).
  • Demonstrated enhanced aggregation- and solid-state fluorescence due to noncovalent interactions and successful application in stimuli-responsive sensors and live-cell imaging.

Conclusions:

  • The designed DPE-based AIEgens exhibit desirable red-light emission and tunable properties.
  • These molecules serve as a versatile platform for developing advanced functional materials.
  • The study highlights the potential of these AIEgens for smart sensors and bioimaging applications.