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

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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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Perylene
Self assembly
Derivatives
Water
Physical properties
Chemical analysis

Keywords

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

Cite this

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title = "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.",
keywords = "nanoparticles, oligomers, photophysics, self-assembly, supramolecular chemistry",
author = "J. Schill and L.G. Milroy and J.A.M. Lugger and A.P.H.J. Schenning and L. Brunsveld",
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Relationship between side-chain polarity and the self-assembly characteristics of perylene diimide derivatives in aqueous solution. / Schill, J.; Milroy, L.G.; Lugger, J.A.M.; Schenning, A.P.H.J.; Brunsveld, L.

In: ChemistryOpen, Vol. 6, No. 2, 01.04.2017, p. 266-272.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Relationship between side-chain polarity and the self-assembly characteristics of perylene diimide derivatives in aqueous solution

AU - Schill, J.

AU - Milroy, L.G.

AU - Lugger, J.A.M.

AU - Schenning, A.P.H.J.

AU - Brunsveld, L.

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N2 - 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.

AB - 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.

KW - nanoparticles

KW - oligomers

KW - photophysics

KW - self-assembly

KW - supramolecular chemistry

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