Issue 26, 2020

Chemiluminescent self-reporting supramolecular transformations on macromolecular scaffolds

Abstract

We introduce the synthesis of a self-reporting system with chemiluminescent output, which is regulated via dynamic supramolecular complex formation. By free radical polymerization and subsequent post-polymerization modification, a copolymer decorated with luminol and superbase (i.e. 1,5,7-triaza-bicyclo-[4.4.0]dec-5-ene (TBD)) moieties was synthesized, which in turn forms supramolecular host–guest-complexation with randomly methylated β-cyclodextrin (Me-β-CD). Upon hydrogen peroxide addition, the host–guest-interactions with the self-assembly are broken, and the luminol is oxidized to 3-aminophthalic acid (3-APA). Critically, no additional base, buffer or catalyst is required to generate the striking blue light emission of the polymeric system that is detectable by the naked eye. Thus, a fast and easy detection of reactive oxygen species (ROS), such as hydrogen peroxide, under mild conditions is established. The self-reporting system and its chemiluminescent properties are characterized by 1D and 2D NMR spectroscopy (particularly NOESY), dynamic light scattering (DLS), UV/Vis spectroscopy and chemiluminescence (CL) measurements.

Graphical abstract: Chemiluminescent self-reporting supramolecular transformations on macromolecular scaffolds

Supplementary files

Article information

Article type
Paper
Submitted
29 Feb 2020
Accepted
15 May 2020
First published
19 May 2020
This article is Open Access
Creative Commons BY-NC license

Polym. Chem., 2020,11, 4213-4220

Chemiluminescent self-reporting supramolecular transformations on macromolecular scaffolds

C. M. Geiselhart, H. Mutlu, P. Tzvetkova and C. Barner-Kowollik, Polym. Chem., 2020, 11, 4213 DOI: 10.1039/D0PY00332H

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