Relationship between side-chain polarity and the self-assembly characteristics of perylene diimide derivatives in aqueous solution

J. Schill, L.G. Milroy, J.A.M. Lugger, A.P.H.J. Schenning, L. Brunsveld

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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.

Original languageEnglish
Pages (from-to)266-272
Number of pages7
JournalChemistryOpen
Volume6
Issue number2
DOIs
Publication statusPublished - 1 Apr 2017

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Keywords

  • nanoparticles
  • oligomers
  • photophysics
  • self-assembly
  • supramolecular chemistry

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