Issue 10, 2024

Triazatriangulenium salts – hosts and guests in supramolecular assemblies in solution

Abstract

Self-assembly of triazatriangulenium dyes (TATA) bearing C3-C8 substituents and their interaction with aromatic compounds were studied. The dyes with alkyl chains longer than C5 were strongly aggregated in solution, while those with shorter alkyl chains formed hetero-stacks with aromatic compounds in chloroform. Anthracene, pyrene, coronene, and a naphthalene diimide dye formed heterostacks in solution with association constants 104 M−1. Anthracene and pyrene-based water-soluble cyclophanes were designed to investigate host–guest complexes with TATA dyes in an aqueous solution. Experimental and theoretical investigations suggest that only pyrene-based cyclophane is able to encapsulate TATA dyes. These self-assembled structures constitute new supramolecular motifs to construct multilayered organic structures.

Graphical abstract: Triazatriangulenium salts – hosts and guests in supramolecular assemblies in solution

Supplementary files

Article information

Article type
Research Article
Submitted
18 Mar 2024
Accepted
02 Apr 2024
First published
04 Apr 2024
This article is Open Access
Creative Commons BY license

Org. Chem. Front., 2024,11, 2922-2927

Triazatriangulenium salts – hosts and guests in supramolecular assemblies in solution

S. Sarkar, M. Böck, A. Uhl, A. Agafontsev, J. Schatz and E. A. Kataev, Org. Chem. Front., 2024, 11, 2922 DOI: 10.1039/D4QO00500G

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