Issue 9, 2024

Polymerizable BODIPY probe crosslinker for the molecularly imprinted polymer-based detection of organic carboxylates via fluorescence

Abstract

This contribution reports the development of a polymerizable BODIPY-type fluorescent probe targeting small-molecule carboxylates for incorporation into molecularly imprinted polymers (MIPs). The design of the probe crosslinker includes a urea recognition site π-conjugated to the 3-position of the BODIPY core and two methacrylate moieties. Titration experiments with a carboxylate-expressing antibiotic, levofloxacin (LEVO), showed a blue shift of the absorption band as well as a broadening and decrease in emission, attributed to hydrogen bonding between the probe's urea group and the carboxylate group of the antibiotic. Using this probe crosslinker, core–shell particles with a silica core and a thin MIP shell were prepared for the detection of LEVO. The MIP exhibited highly selective recognition of LEVO, with an imprinting factor of 18.1 compared to the non-imprinted polymer. Transmission electron microscopy confirmed the core–shell structure and spectroscopic studies revealed that the receptor's positioning leads to a unique perturbation of the polymethinic character of the BODIPY chromophore, entailing the favourable responses. These features are fully preserved in the MIP, whereas no such response was observed for competitors such as ampicillin. The sensory particles allowed to detect LEVO down to sub-micromolar concentrations in dioxane. We have developed here for the first time a BODIPY probe for organic carboxylates and incorporated it into polymers using the imprinting technique, paving the way for BODIPY-type fluorescent MIP sensors.

Graphical abstract: Polymerizable BODIPY probe crosslinker for the molecularly imprinted polymer-based detection of organic carboxylates via fluorescence

Supplementary files

Article information

Article type
Paper
Submitted
28 Jul 2023
Accepted
08 Mar 2024
First published
21 Mar 2024
This article is Open Access
Creative Commons BY license

Mater. Adv., 2024,5, 3783-3793

Polymerizable BODIPY probe crosslinker for the molecularly imprinted polymer-based detection of organic carboxylates via fluorescence

Y. Sun, K. Gawlitza, V. Valderrey, J. Bell and K. Rurack, Mater. Adv., 2024, 5, 3783 DOI: 10.1039/D3MA00476G

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.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements