4.8 Article

Fluorescence Switching of Imidazo[1,5-a]pyridinium Ions: pH-Sensors with Dual Emission Pathways

Journal

ORGANIC LETTERS
Volume 14, Issue 12, Pages 3162-3165

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol3012524

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Funding

  1. DTRA/Army Research Office [W911NF-07-1-0533]
  2. Indiana University

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Imidazo[1,5-a]pyridinium ions are identified as highly emissive and water-soluble fluorophores accessed by an efficient three-component coupling reaction. Synthetic modifications of groups conjugated to the polyheterocyclic core are shown to profoundly impact the emission properties of these molecules. Notably, two structural isomers of functionalized imidazo[1,5-a]pyridinium ions were found to exhibit distinct de-excitation pathways, which are responsible for either a fluorescence turn-on or ratiometric response to pH change.

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