Issue 24, 2023

Comparative study of the self-assembly behaviour of 3-chloro-4-hydroxy-phenylazo dyes

Abstract

The complexity of intermolecular interactions and the difficulty to predict assembly behaviour solely based on chemical constitution was demonstrated by studying the self-assembly of three one-fold negatively charged 3-chloro-4-hydroxy-phenylazo dyes (Yellow, Blue and Red). Dye self-assembly was investigated using UV/vis- and NMR-spectroscopy, light- and small-angle neutron scattering. Significant differences between the three dyes were observed. While Yellow does not self-assemble, Red assembles into higher-order aggregates and Blue forms well-defined H-aggregate dimers with a dimerization constant of KD = (728 ± 8) L mol−1. Differences between dyes were suggested to emerge from variations in the propensity to form π–π-interactions due to electrostatic repulsion, sterical constraints and hydrogen-bonding interactions.

Graphical abstract: Comparative study of the self-assembly behaviour of 3-chloro-4-hydroxy-phenylazo dyes

Supplementary files

Article information

Article type
Paper
Submitted
14 Apr 2023
Accepted
06 Jun 2023
First published
09 Jun 2023
This article is Open Access
Creative Commons BY license

Soft Matter, 2023,19, 4579-4587

Comparative study of the self-assembly behaviour of 3-chloro-4-hydroxy-phenylazo dyes

W. Müller, R. Schweins, B. Nöcker, H. Egold and K. Huber, Soft Matter, 2023, 19, 4579 DOI: 10.1039/D3SM00500C

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