Quadrupolar, Highly Polarized Dyes: Emission Dependence on Viscosity and Selective Mitochondria Staining

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Authors
Tasior, Mariusz
Vakuliuk, Olena
Wrzosek, Antoni
Vullev, Valentine I.
Szewczyk, Adam
Jacquemin, Denis
Gryko, Daniel T.
Date
2024
Journal Title
Journal ISSN
Volume Title
Publisher
American Chemical Society
License
Creative Commons License
Attribution-NonCommercial-NoDerivatives 4.0 International
Abstract
Quadrupolar A-D-A-type 1,4-dihydropyrrolo[3,2-b]pyrroles (DHPPs) bearing pyridinium and quinolinium substituents emit in the 500–600 nm region. The enhancement of electronic communication between the electron-rich heterocyclic core and electron-deficient peripheral substituents turned out to be crucial for achieving emission enhancement in viscous media. DHPP bearing two 4-pyridinium substituents has optical brightness 34,000 in glycerol and only 700 in MeOH, as evidenced by measurements of the emission intensity and fluorescence lifetimes in a series of polar solvents. Such behavior makes it an excellent candidate for viscosity probes in fluorescence microscopy, as demonstrated by the fluorescence imaging of H9C2 cardiomyocytes.
Description
Keywords
dyes/pigments  fluorescence  heterocycles  donor−acceptor systems  viscosity
Citation
ACS Org. Inorg. Au 2024, 4, 2, 248–257 ; https://doi.org/10.1021/acsorginorgau.3c00035
URI
https://open.icm.edu.pl/handle/123456789/24184
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