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March 15, 2026Angewandte Chemie International Edition6 citations

Extended Fused Carbazole‐BODIPY, High Brightness NIR Organic Dyes

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FCFabien CeugnietVOValentin OttPRPascal Retailleau

Key Points

  • This research aims to develop high-brightness NIR organic dyes for enhanced bioimaging applications.
  • Synthesize hetero-substituted-fused BODIPY dyes using Stille couplings and silver-mediated cyclization.
  • Evaluate the photophysical properties, including absorption and fluorescence quantum yields.
  • Test the efficacy of the dyes for in vivo imaging in murine models.
  • New dyes exhibit brightness and emission maxima up to 852 nm.
  • Demonstrated fluorescence quantum yields up to 0.73.
  • Tumor detection achieved at doses as low as 0.2 nmol with tumor-to-muscle ratios greater than 4.

Abstract

ABSTRACT Fluorescence‐based bioimaging enables noninvasive visualization of molecular and cellular processes with high sensitivity and without ionizing radiation. However, conventional fluorophores emitting in the visible or near‐red infrared I (NIR‐I) (650–800 nm) regions suffer from limited tissue penetration and scattering. Extending fluorescence emission into the deeper NIR region represents a promising strategy to overcome these drawbacks, yet achieving high brightness and stability in organic dyes remains a major challenge. We report an original family of hetero‐substituted‐fused boron‐dipyrromethene (BODIPY) dyes bearing carbazole and thienyl donors that exhibit record brightness and emission maxima up to 852 nm in toluene. The synthetic route combines successive Stille couplings from a 2,6‐dibromo‐3,5‐diiodo‐BODIPY precursor and an unprecedented silver(I)‐mediated oxidative cyclization, affording high yields and suppressing undesired chlorination. The resulting dyes display intense absorption ( ε = 1.8–2.5 × 10 5 M − 1 cm − 1 ) and exceptional fluorescence quantum yields ( Φ up to 0.73). Encapsulation in silica nanoparticles (NPs) preserves their photophysical properties and enables efficient NIR‐II in vivo imaging in mice, allowing tumor detection at doses as low as 0.2 nmol with tumor‐to‐muscle ratios > 4. These fused BODIPY derivatives rank among the brightest NIR fluorophores reported to date and open new avenues for high‐contrast deep‐tissue imaging and image‐guided surgery.

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Cite This Study

Ceugniet et al. (2026) studied this question.

synapsesocial.com/papers/69b5ff6e83145bc643d1bfa5https://doi.org/10.1002/anie.202526011
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