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Bulky Barbiturates as Non‐Toxic Ionic Dye Insulators for Enhanced Emission in Polymeric Nanoparticles
Author(s) -
Andreiuk Bohdan,
Aparin Ilya O.,
Reisch Andreas,
Klymchenko Andrey S.
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202101986
Subject(s) - counterion , chemistry , nanoparticle , fluorescence , photochemistry , cationic polymerization , rhodamine b , ionic bonding , combinatorial chemistry , organic chemistry , materials science , nanotechnology , ion , photocatalysis , physics , quantum mechanics , catalysis
Abstract Bulky hydrophobic counterions (weakly coordinating anions) can insulate ionic dyes against aggregation‐caused quenching (ACQ) and enable preparation of highly fluorescent dye‐loaded nanoparticles (NPs) for bioimaging, biosensing and light harvesting. Here, we introduce a family of hydrophobic anions based on fluorinated C ‐acyl barbiturates with delocalized negative charge and bulky non‐polar groups. Similarly to fluorinated tetraphenylborates, these barbiturates prevent ACQ of cationic dye alkyl rhodamine B inside polymer NPs made of biodegradable poly(lactic‐co‐glycolic acid) (PLGA). Their efficiency to prevent ACQ increases for analogues with higher acidity and bulkiness. Their structure controls dye‐dye communication, yielding bright NPs with on/off switching or stable emission. They enhance dye encapsulation inside NPs, allowing intracellular imaging without dye leakage. Compared to fluorinated tetraphenylborates known as cytotoxic transmembrane ion transporters, the barbiturates display a significantly lower cytotoxicity. These chemically available and versatile barbiturate derivatives are promising counterion scaffolds for preparation of bright non‐toxic fluorescent nanomaterials.