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Chemiluminescent self-reporting supramolecular transformations on macromolecular scaffolds

Geiselhart, Christina M. 1; Mutlu, Hatice 1; Tzvetkova, Pavleta 2; Barner-Kowollik, Christopher 1
1 Institut für Technische Chemie und Polymerchemie (ITCP), Karlsruher Institut für Technologie (KIT)
2 Institut für Organische Chemie (IOC), Karlsruher Institut für Technologie (KIT)


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.

Verlagsausgabe §
DOI: 10.5445/IR/1000122313
Veröffentlicht am 03.08.2020
DOI: 10.1039/d0py00332h
Web of Science
Zitationen: 5
Zitationen: 6
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Biologische Grenzflächen (IBG)
Institut für Technische Chemie und Polymerchemie (ITCP)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2020
Sprache Englisch
Identifikator ISSN: 1759-9954, 1759-9962
KITopen-ID: 1000122313
HGF-Programm 47.02.03 (POF III, LK 01) Zellpopul.auf Biofunk.Oberflächen IBG-3
Erschienen in Polymer chemistry
Verlag Royal Society of Chemistry (RSC)
Band 11
Heft 26
Seiten 4213–4220
Vorab online veröffentlicht am 19.05.2020
Nachgewiesen in Web of Science
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