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BOIMPY: Fluorescent Boron Complexes with Tunable and Environment-Responsive Light-Emitting Properties.

Boran Lee1, Byung Gyu Park2, Wansang Cho1

  • 1Department of Chemistry, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul, 08826, Korea.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|October 19, 2016
PubMed
Summary

New boron complexes, BOIMPYs, mimic BODIPY dyes for advanced imaging. These fluorophores exhibit environment-sensitive emission, enabling targeted live-cell imaging of lipid droplets with high resolution.

Keywords:
boronchelatesconjugationfluorescent probesimaging agents

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Area of Science:

  • Organic Chemistry
  • Photophysics
  • Materials Science

Background:

  • The BODIPY (boron-dipyrromethene) motif is a privileged fluorophore structure.
  • Minimalist structural mimics of BODIPY are sought for novel photophysical properties.
  • Boron complexes with iminopyrrolide ligands offer a new avenue for fluorophore design.

Purpose of the Study:

  • To synthesize and characterize novel air-stable boron complexes (BOIMPYs) as BODIPY mimics.
  • To investigate the photophysical properties and structure-dependent emission mechanisms of BOIMPYs.
  • To develop a BOIMPY-based bioprobe for live-cell imaging.

Main Methods:

  • Synthesis of boron complexes 1-5 using N-aryl iminopyrrolide ligands.
  • Spectroscopic studies (absorption, emission) to analyze photophysical properties.
  • Comparative studies on compounds 1-4 to understand de-excitation mechanisms.
  • Live-cell fluorescence imaging using bioprobe molecule 5.

Main Results:

  • Air-stable BOIMPY fluorophores with low molecular symmetry were successfully prepared.
  • BOIMPYs exhibit emission from charge-transfer (CT) excited states with large Stokes shifts and minimal self-quenching.
  • De-excitation mechanisms are sensitive to solvent polarity and protonation states, tunable via conformational twisting and donor-acceptor interactions.
  • Bioprobe molecule 5 specifically stains lipid droplets in live cells without toxicity.

Conclusions:

  • BOIMPYs represent a versatile class of fluorophores with tunable, environment-sensitive emission properties.
  • The structure-property relationships in BOIMPYs allow for rational design of functional molecules.
  • BOIMPY-based bioprobe 5 demonstrates potential for advanced biological imaging and sensing applications.