Universität zu Köln

Atar, Murat, Taspinar, Oemer, Hanft, Sebastian, Goldfuss, Bernd ORCID: 0000-0002-1814-8818, Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 and Griesbeck, Axel G. (2019). Hydrogen Peroxide Sensors Based on Fluorescence Quenching of the 2-AminobenzimidazoleFluorophore. J. Org. Chem., 84 (24). S. 15972 - 15978. WASHINGTON: AMER CHEMICAL SOC. ISSN 1520-6904

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Abstract

The fluorescence emission of the parent 2-aminobenzimidazole (ABZ, 1), the mono- and disubstituted derivatives (2, 3), 2-aminonaphthoimidazole (4), and 4-amino dinaphthodiazepine 5 (lambda(em) = 315-400 nm) is strongly quenched in the presence of aqueous hydrogen peroxide. The quenching process is dual: for diazepine 5, quenching is dynamic at lower H2O2 concentrations with linear reduction of the fluorescence lifetime from 4.3 to 2.6 ns. At higher H2O2 concentrations, a second species appears in the absorption and emission spectra with fluorescence lifetimes of 1.3 ns, indicating the formation of a new (ground-state) hydrogen-bonded ABZ-H2O2 complex (static quenching). Sensors 1 and 2 show also dual quenching that fits with a static 1:1 and 1:2 model with K-1:1 = 8(11) M-1 and K-1:2 = 21(147) M(-)1 for 1(2). The formation of a 1:2 complex (1: (H2O2)(2)) is also supported by density functional theory (DFT) calculations and spectra simulations.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Atar, Murat UNSPECIFIED UNSPECIFIED UNSPECIFIED Taspinar, Oemer UNSPECIFIED UNSPECIFIED UNSPECIFIED Hanft, Sebastian UNSPECIFIED UNSPECIFIED UNSPECIFIED Goldfuss, Bernd UNSPECIFIED orcid.org/0000-0002-1814-8818 UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED Griesbeck, Axel G. UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-124131
DOI:	10.1021/acs.joc.9b02262
Journal or Publication Title:	J. Org. Chem.
Volume:	84
Number:	24
Page Range:	S. 15972 - 15978
Date:	2019
Publisher:	AMER CHEMICAL SOC
Place of Publication:	WASHINGTON
ISSN:	1520-6904
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language SELECTIVE RECOGNITION; BENZIMIDAZOLE; RECEPTOR; OXIDATION; PHOTOCHEMISTRY; HETEROCYCLICS; PHOTOLYSIS; PROBES Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/12413