Issue 2, 2025

Internally diketopyrrolopyrrole-bridged bis-anthracene macrocycle: a multifunctional fluorescent platform

Abstract

A covalently bridged macrocycle (5) comprising two anthracene strands connected at the lactam positions of a diketopyrrolopyrrole (DPP) chromophore has been constructed. The crystal structure reveals that the central DPP chromophore is wrapped with the externally twisted bis-anthracene macrocycle. The internally bridged macrocycle architecture endows 5 with multifunctional properties. Due to shielding by the double anthracene straps, 5a and a polymer derived from it, DPP-Cycle, display strong fluorescence emission features in both organic media and the solid state. Moreover, the emission colors of these macrocyclic materials can be effectively tuned through external stimuli such as mechanical and thermal treatments, as well as solvent fuming. Compound 5a is stable in the presence of most metal cations but degrades rapidly when it comes in contact with Cu2+ in acetonitrile. This decomposition, which is thought to involve a reaction at the central DPP via a radical-mediated mechanism, was found to be accelerated in 5a compared to the non-cyclic analogue 2a. This leads us to suggest that internally bridged macrocycles, such as those described here, may have a role to play as fluorescent Cu2+ sensors. Finally, the high fluorescence of 5a in the solid state enables its use in the area of latent fingerprint (LFP) imaging.

Graphical abstract: Internally diketopyrrolopyrrole-bridged bis-anthracene macrocycle: a multifunctional fluorescent platform

Supplementary files

Article information

Article type
Edge Article
Submitted
07 Sep 2024
Accepted
01 Dec 2024
First published
03 Dec 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2025,16, 910-919

Internally diketopyrrolopyrrole-bridged bis-anthracene macrocycle: a multifunctional fluorescent platform

H. Zhou, Y. Zhang, Z. Zheng, J. Wan, H. Zhang, K. Lin, J. L. Sessler and H. Wang, Chem. Sci., 2025, 16, 910 DOI: 10.1039/D4SC06067A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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