The effect of boronic acid-positioning in an optical glucose-sensing ensemble

Autor:	Nichol A. Baxter, Marilyn M. Olmstead, David B. Cordes, Soya Gamsey, Ritchie A. Wessling, Bakthan Singaram, Zachary Sharrett
Rok vydání:	2006
Předmět:	inorganic chemicals Quenching (fluorescence) Organic Chemistry Potentiometric titration Viologen Nuclear magnetic resonance spectroscopy Photochemistry Biochemistry Fluorescence Pyranine chemistry.chemical_compound chemistry Intramolecular force Drug Discovery medicine Boronic acid medicine.drug
Zdroj:	Tetrahedron. 62:6321-6331
ISSN:	0040-4020
DOI:	10.1016/j.tet.2006.04.047
Popis:	The quenching of the anionic dye 8-hydroxypyrene-1,3,6-trisulfonic acid trisodium salt (pyranine) with three different boronic acid-substituted benzyl viologens was determined, and the fluorescence signal modulation obtained upon addition of glucose to the dye/quencher system was also studied. The benzyl viologen that contains boronic acids in the ortho-position (o-BBV) was found to display unique behavior, which can be rationalized by a charge neutralization mechanism facilitated by an intramolecular interaction between sp3 boronate and the quaternary nitrogen of the viologen. Potentiometric titration and 11B NMR spectroscopy were used to generate pH profiles for the boronic acids, which provide additional evidence for the proposed mechanism.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::7466359e5ad17c0c39b6d596cc74ed84 https://doi.org/10.1016/j.tet.2006.04.047 Zobrazit plný text záznamu Full Text from ScienceDirect