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A Mechanofluorochromic Push-Pull Small Molecule with Aggregation-Controlled Linear and Nonlinear Optical Properties.

Yue Jiang1,2, Denis Gindre1, Magali Allain1

  • 1Moltech-Anjou, CNRS UMR 6200, University of Angers 2 Bd Lavoisier, 49045, Angers, France.

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Summary

This study introduces a novel push-pull molecule with aggregation-induced emission properties. The material displays mechanofluorochromism and aggregation-induced second-harmonic generation in self-organized films.

Keywords:
aggregationsmechanochromismmetastablenonlinear opticspush-pull molecules

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photophysics

Background:

  • Aggregation-induced emission (AIE) is a photophysical phenomenon where luminogens are non-emissive in solution but become highly emissive in the aggregated state.
  • Push-pull molecules, featuring electron-donating and electron-withdrawing groups, are crucial for developing advanced functional materials.

Purpose of the Study:

  • To synthesize and characterize a novel diphenylamine-based push-pull molecule with an oligo-oxyethylene chain.
  • To investigate the aggregation-induced emission (AIE) properties and solvent-dependent emission of the synthesized compound.
  • To explore the solid-state properties, including mechanofluorochromism and aggregation-induced second-harmonic generation (SHG) in self-organized films.

Main Methods:

  • Synthesis of a diphenylamine derivative substituted with an oligo-oxyethylene chain.
  • Spectroscopic analysis to determine photophysical properties (emission wavelength, AIE behavior).
  • Fabrication of amorphous films via spin-casting and observation of self-organization into crystalline films.
  • Mechanical stimulation and optical microscopy to study mechanofluorochromism.
  • Second-harmonic generation (SHG) measurements on the organized films.

Main Results:

  • The synthesized molecule exhibits aggregation-induced emission (AIE) with a tunable emission wavelength dependent on the solvent environment.
  • Spin-cast amorphous films of the compound spontaneously reorganize into colorless crystalline films.
  • These crystalline films demonstrate significant mechanofluorochromism, changing emission upon mechanical stress.
  • The material also exhibits aggregation-induced second-harmonic generation (SHG) in its organized state.

Conclusions:

  • The novel push-pull molecule is a promising AIE luminogen with potential applications in sensing and optoelectronics.
  • The observed mechanofluorochromism and aggregation-induced SHG highlight the material's responsiveness and nonlinear optical properties.
  • The self-organization capability of the films offers a pathway for fabricating functional solid-state devices.