The Partner Does Matter: The Structure of Heteroaggregates of Acridine Orange in Water

• Main Author: Ilya G. Shenderovich
• Format: Article
• Language: English
• Published: MDPI AG 2019-08-01
• Series: Molecules
• Subjects: NMR spectroscopy; self-assembly; nitrogen heterocycles; fluorescent probes
• Online Access: https://www.mdpi.com/1420-3049/24/15/2816

Self-assembly of organic molecules in aqueous solutions is governed by a delicate entropy/enthalpy balance. Even small changes in their intermolecular interactions can cause critical changes in the structure of the aggregates and their spectral properties. The experimental results reported here demonstrate that protonated cations of acridine orange, acridine, and acridin-9-amine form stable J-heteroaggregates when in water. The structures of these aggregates are justified by the homonuclear ¹H cross-relaxation nuclear magnetic resonance (NMR). The absorption and fluorescence of these aggregates deviate characteristically from the known H-homoaggregates of the protonated cations of acridine orange. The latter makes acridine orange a handy optical sensor for soft matter studies.