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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)

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.


Verlagsausgabe §
DOI: 10.5445/IR/1000122313
Veröffentlicht am 03.08.2020
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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