Microwave-assisted synthesis of new triangulenium dyes for lifetime imaging microscopy (FLIM)

04 June 2025, Version 1

Abstract

We introduce a novel microwave-assisted method for the rapid and efficient synthesis of triangulene dyes, enabling the creation of a broader range of these fluorophores, which are characterized by very long fluorescence lifetimes. We prepared different azadioxatriangulenium (ADOTA) and diazaoxatriangulenium (DAOTA) derivatives and thoroughly characterize their pho- tophysical properties. We investigated their solvatochromic properties and effects from solvent, aided by computational chemistry results. We employed the new ADOTAs and DAOTAs in different modalities of microscopy in cellulo, including confocal, fluores- cence lifetime imaging microscopy (FLIM), and super-resolution structured illumination microscopy (SIM). Most of the candidates accumulate in mitochondria, where they undergo electron transfer-driven quenching, which makes them exceptionally well-suited for providing distinct contrast for mitochondrial identification in FLIM microscopy.

Keywords

Dyes
Cell imaging
Advanced microscopy
Solvatochromism
Photophysics

Supplementary materials

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Description
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Supporting Information (PDF)
Description
The Supporting Information file (PDF) includes supplementary experimental section, detailed information on the synthesis and characterization of the new dyes, including 1H- and 13C-NMR spectra, Supporting Figures S1-S5, and Supporting Tables S1-S9.
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TD-DFT coordinates
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This supplementary file (XLSX) contains data sheets with xyz coordinates from TD-DFT geometry optimization of the 8 dyes.
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