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- Title
Bulky Barbiturates as Non‐Toxic Ionic Dye Insulators for Enhanced Emission in Polymeric Nanoparticles.
- Authors
Andreiuk, Bohdan; Aparin, Ilya O.; Reisch, Andreas; Klymchenko, Andrey S.
- 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.
- Subjects
BARBITURATES; BASIC dyes; NANOPARTICLES; RHODAMINE B; DYES &; dyeing
- Publication
Chemistry - A European Journal, 2021, Vol 27, Issue 50, p12877
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202101986