PyrAtes: Modular Organic Salts with Large Stokes Shifts for Fluo-rescence Microscopy

Abstract

The deployment of small-molecule fluorescent agents plays an ever-growing role in medicine and drug development. Herein, we complement the portfolio of powerful fluorophores, reporting the serendipitous discovery and development of a novel class with an imidazo[1,2-a]pyridinium triflate core, which we term PyrAtes. These fluorophores are synthesized in a single step from readily available materials (>60 examples) and display Stokes shifts as large as 240 nm, while also reaching NIR-I emissions at λ_max as long as 720 nm. Computational studies allow the development of a platform for the prediction of λ_max and λ_Em. Furthermore, we demonstrate the compatibility of these novel fluorophores with live cell imaging in HEK293 cells, suggesting PyrAtes as potent intracellular markers.

Keywords: Dyes; Fluorescence; Fluorophore; Imidazo[1,2-a]pyridinium; Stokes shift.