Acid-Triggered Switchable Near-Infrared/Shortwave Infrared Absorption and Emission of Indolizine-BODIPY Dyes

Fluorescent organic dyes that absorb and emit in the near-infrared (NIR, 700–1000 nm) and shortwave infrared (SWIR, 1000–1700 nm) regions have the potential to produce noninvasive high-contrast biological images and videos. BODIPY dyes are well known for their high quantum yields in the visible ener...

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Bibliographic Details
Published in:Molecules
Main Authors: Matthew A. Saucier, Cameron Smith, Nicholas A. Kruse, Nathan I. Hammer, Jared H. Delcamp
Format: Article
Language:English
Published: MDPI AG 2023-01-01
Subjects:
near-infrared (NIR) emission
shortwave infrared (SWIR) emission
BODIPY
indolizine
fluorescence imaging agents
Online Access:https://www.mdpi.com/1420-3049/28/3/1287
Description
Summary:Fluorescent organic dyes that absorb and emit in the near-infrared (NIR, 700–1000 nm) and shortwave infrared (SWIR, 1000–1700 nm) regions have the potential to produce noninvasive high-contrast biological images and videos. BODIPY dyes are well known for their high quantum yields in the visible energy region. To tune these chromophores to the NIR region, fused nitrogen-based heterocyclic indolizine donors were added to a BODIPY scaffold. The indolizine BODIPY dyes were synthesized via microwave-assisted Knoevenagel condensation with indolizine aldehydes. The non-protonated dyes showed NIR absorption and emission at longer wavelengths than an aniline benchmark. Protonation of the dyes produced a dramatic 0.35 eV bathochromic shift (230 nm shift from 797 nm to 1027 nm) to give a SWIR absorption and emission (λ<sub>max</sub><sup>emis</sup> = 1061 nm). Deprotonation demonstrates that material emission is reversibly switchable between the NIR and SWIR.
ISSN:1420-3049

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