Mechanochemical Release of Fluorophores from a “Flex‐activated” Mechanophore

Author:

Yang Fan12,Geng Ting3,Shen Hang4,Kou Yan1,Xiao Guanjun3,Zou Bo3,Chen Yulan1ORCID

Affiliation:

1. State Key Laboratory of Supramolecular Structure and Materials College of Chemistry Jilin University Changchun 130012 P. R. China

2. Fujian Provincial Key Laboratory of Ecology-Toxicological Effects & Control for Emerging Contaminants Key Laboratory of Ecological Environment and Information Atlas College of Environmental and Biological Engineering Putian University Putian 351100 P. R. China

3. State Key Laboratory of Superhard Materials College of Physics Jilin University Changchun 130012 P. R. China

4. College of Chemistry Chemical Engineering and Materials Science Soochow University Suzhou 215123 P. R. China

Abstract

AbstractOptical force probes that can release force‐dependent and visualized signals with minimal changes in the polymer main chains under mechanical load are highly sought after but currently limited. In this study, we introduce a flex‐activated mechanophore (FA) based on the Diels–Alder adduct of anthracene and dimethyl acetylenedicarboxylatea that exhibits turn‐on mechanofluorescence. We demonstrate that when FA is incorporated into polymer networks or in its crystalline state, it can release fluorescent anthracenes through a retro‐Diels–Alder mechanochemical reaction under compression or hydrostatic high pressure, respectively. The flex‐activated mechanism of FA is successfully confirmed. Furthermore, we systematically modulate the force delivered to the mechanophore by varying the crosslinking density of the networks and the applied macroscopic pressures. This modulation leads to incremental increases in mechanophore activation, successive release of anthracenes, and quantitative enhancement of fluorescence intensity. The exceptional potential of FA as a sensitive force probe in different bulk states is highlighted, benefiting from its unique flex‐activated mode with highly emissive fluorophore releasing. Overall, this report enriches our understanding of the structures and functions of flex‐activated mechanophores and polymeric materials.

Funder

Fundamental Research Funds for the Central Universities

National Natural Science Foundation of China

State Key Laboratory of Supramolecular Structure and Materials

Publisher

Wiley

Subject

General Medicine

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