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Relationship between Side-Chain Polarity and the Self-Assembly Characteristics of Perylene Diimide Derivatives in Aqueous Solution.

ABSTRACT: Perylene-3,4,9,10-tetracarboxylic acid diimides (PDIs) have recently gained considerable interest for water-based biosensing applications. PDIs have been studied intensively in the bulk state, but their physical properties in aqueous solution in interplay with side-chain polarity are, however, poorly understood. Therefore, three perylene diimide based derivatives were synthesized to study the relationship between side-chain polarity and their self-assembly characteristics in water. The polarity of the side chains was found to dictate the size and morphology of the formed aggregates. Side-chain polarity rendered the self-assembly and photophysical properties of the PDIs-both important for imminent water-based applications-and these were revealed to be especially responsive to changes in solvent composition.

SUBMITTER: Schill J

PROVIDER: S-EPMC5390792 | biostudies-literature | 2017 Apr

REPOSITORIES: biostudies-literature

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Relationship between Side-Chain Polarity and the Self-Assembly Characteristics of Perylene Diimide Derivatives in Aqueous Solution.

Schill Jurgen J Milroy Lech-Gustav LG Lugger Jody A M JAM Schenning Albertus P H J APHJ Brunsveld Luc L

ChemistryOpen 20170120 2

Perylene-3,4,9,10-tetracarboxylic acid diimides (PDIs) have recently gained considerable interest for water-based biosensing applications. PDIs have been studied intensively in the bulk state, but their physical properties in aqueous solution in interplay with side-chain polarity are, however, poorly understood. Therefore, three perylene diimide based derivatives were synthesized to study the relationship between side-chain polarity and their self-assembly characteristics in water. The polarity ...[more]

PMID: 28413763

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