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Photophysical Characteristics of Polarity‐Sensitive and Lipid Droplet‐Specific Phenylbenzothiadiazoles
Author(s) -
Colas Kilian,
Doloczki Susanne,
Kesidou Aikaterina,
SaineroAlcolado Lourdes,
RodriguezGarcia Aida,
ArsenianHenriksson Marie,
Dyrager Christine
Publication year - 2021
Publication title -
chemphotochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.13
H-Index - 18
ISSN - 2367-0932
DOI - 10.1002/cptc.202100040
Subject(s) - solvatochromism , excited state , polarity (international relations) , substituent , fluorescence , photochemistry , chemistry , stain , lipid droplet , intramolecular force , luminescence , materials science , molecule , staining , stereochemistry , organic chemistry , optoelectronics , biochemistry , optics , medicine , physics , pathology , nuclear physics , cell
Abstract In this study, we present a series of solvatochromic phenylbenzothiadiazoles that display dual emission from the locally excited (LE) and intramolecular charge transfer (ICT) excited states. The donor‐acceptor derivatives are highly sensitive to polarity changes, which can be monitored by differences in emission efficiency, spectroscopic shifts and variations of the LE/ICT ratio. One of the compounds in the series, containing a thiomethyl substituent, emerged as an excellent blue emitting stain for intracellular lipid droplets, a biomarker for various types of cancer. In addition, a non‐emissive nitro derivative becomes fluorescent upon bioreduction in hypoxic cancer cells and accumulates in lipid droplets with a high signal‐to‐background ratio.