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Stepwise Modulation of Bridged Single-Benzene-Based Fluorophores for Materials Science.

Alexander Huber1, Laura Schmidt2, Tim Gatz1

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Chemistry (Weinheim an Der Bergstrasse, Germany)
|December 23, 2024
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Summary

Researchers developed novel, small single-benzene-based fluorophores (SBBFs) with tunable, full-color emission. These accessible SBBFs show potential for advanced materials and biomedical applications.

Keywords:
Single-Benzene Based Fluorophores (SBBF)Solution- and Solid-State Emission (SSSE)Stereolithography (SLA)Structure-property relationshipWhite light emission (WLE)

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Photophysics

Background:

  • Shift towards smaller, simpler fluorophores with improved solubility and synthesis.
  • Need for novel emitters with tunable photophysical properties for diverse applications.

Purpose of the Study:

  • Investigate photophysical properties of five novel single-benzene-based fluorophores (SBBFs).
  • Evaluate solution and solid-state emission (SSSE) characteristics.
  • Explore potential applications in materials science and biomedical fields.

Main Methods:

  • Synthesis of five SBBFs derived from a terephthalonitrile core with varying oxygen and nitrogen bridges.
  • Photophysical characterization including photoluminescence quantum yield (PLQY) measurements in DMSO.
  • Compatibility assessment in poly(methyl methacrylate) (PMMA) films and stereolithography (SLA) 3D printing.
  • Density-functional theory (DFT) calculations for theoretical absorption and emission wavelengths.
  • Cellular internalization studies using Pluronic® F-127 nanoparticles.

Main Results:

  • SBBFs exhibit tunable, full-color emission with moderate-to-high PLQY (up to 0.78 in DMSO).
  • Achieved white light emission in solution and 3D-printed materials by controlling compound ratios.
  • Demonstrated excellent compatibility with PMMA films and SLA additive manufacturing.
  • DFT calculations showed good correlation with experimental absorption and emission wavelengths.
  • Successful cellular internalization of SBBFs via Pluronic® F-127 nanoparticles.

Conclusions:

  • Single-benzene-based emitters offer remarkable, tunable photophysical properties.
  • These accessible fluorophores present significant potential for advanced materials and biomedical applications.
  • The study highlights the versatility and practicality of SBBFs in various technological contexts.