Recognition and sensing of biologically relevant anions in alcohol and mixed alcohol-aqueous solutions using charge neutral cleft-like glycol-derived pyridyl-amidothiourea receptors

The Journal of Organic Chemistry
Rebecca M DukeThorfinnur Gunnlaugsson

Abstract

In this paper, the synthesis and the spectroscopic investigation of new colorimetric receptors for anions 3-6, possessing a glycol chain at the 4-position of the pyridyl ring, and 1 and 2, which lack such a chain, and the X-ray crystal structure of 2 is presented. Structures 3-6 are able to bind to anions in competitive media, such as alcohol or in a mixture of methanol and water, where the anion recognition gives rise to changes in the absorption spectra, which is red-shifted, in 1:1 or 1:2 (sensor/anion) stoichiometry. The anion recognition for 1 and 2 was also investigated in organic solvents and in a 4:1 mixture of DMSO/H(2)O. The binding of 1 to anions such as acetate, phosphate, and fluoride was also evaluated using (1)H NMR in DMSO-d(6).

References

Nov 13, 2003·Chemical Reviews·Ramón Martínez-Máñez, Félix Sancenón
Mar 24, 2004·Angewandte Chemie·Alix ArnaudVéronique Wintgens
Dec 17, 2004·Journal of the American Chemical Society·Massimo BoiocchiEnrico Monzani
Jun 30, 2005·Journal of Fluorescence·Thorfinnur GunnlaugssonJuliann Tierney
Nov 18, 2005·Organic Letters·Frederick M PfefferPaul E Kruger
Dec 17, 2005·The Journal of Organic Chemistry·Thorfinnur GunnlaugssonGillian M Hussey
Feb 24, 2006·Chemical Communications : Chem Comm·Louise S EvansRoberto Quesada
Apr 26, 2007·Chemical Communications : Chem Comm·Caroline D B VandevyverJean-Claude G Bünzli
Apr 28, 2007·Organic & Biomolecular Chemistry·Adam J LoweFrederick M Pfeffer
May 24, 2007·Organic & Biomolecular Chemistry·Wen-Xia Liu, Yun-Bao Jiang
May 24, 2007·Organic & Biomolecular Chemistry·Frederick M PfefferKathryn J Sedgwick
Jun 7, 2007·Organic & Biomolecular Chemistry·Frederick M PfefferThorfinnur Gunnlaugsson
Aug 30, 2007·The Journal of Organic Chemistry·Eoin QuinlanThorfinnur Gunnlaugsson
Oct 18, 2007·The Journal of Organic Chemistry·Gareth W BatesPhilip A Gale
Dec 22, 2007·The Journal of Organic Chemistry·Wen-Xia Liu, Yun-Bao Jiang
Jan 17, 2008·Chemical Society Reviews·Philip A GaleJoachim Garric
Apr 11, 2008·Chemical Communications : Chem Comm·Claudia CaltagironeMark E Light
May 21, 2008·The Journal of Physical Chemistry. B·Zhao LiYun-Bao Jiang
Sep 19, 2008·The Journal of Organic Chemistry·Emma B Veale, Thorfinnur Gunnlaugsson
Nov 7, 2008·The Journal of Organic Chemistry·Cidália M G dos SantosThorfinnur Gunnlaugsson
May 14, 2009·Chemical Communications : Chem Comm·Massimo Cametti, Kari Rissanen
Jun 11, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Cidália Maria Gomes Dos Santos, Thorfinnur Gunnlaugsson
Sep 5, 2009·Chemistry, an Asian Journal·Philip A GaleMark E Light
Sep 19, 2009·Organic & Biomolecular Chemistry·Wen-Xia LiuYun-Bao Jiang
Aug 26, 2010·Chemical Society Reviews·Ai-Fang LiYun-Bao Jiang
Sep 8, 2010·Chemical Society Reviews·Valeria AmendolaLorenzo Mosca
Sep 8, 2010·Chemical Society Reviews·Philip A Gale
Sep 8, 2010·Chemical Society Reviews·Benjamin P Hay
Nov 15, 2011·Chemical Society Reviews·Marco WenzelPhilip A Gale

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Citations

May 5, 2017·Journal of the American Chemical Society·Sarah J PikeChristopher A Hunter
Nov 7, 2017·Organic & Biomolecular Chemistry·Sarah J Pike, Christopher A Hunter
Oct 6, 2018·Chemistry : a European Journal·Aleksandr M AgafontsevEvgeny A Kataev
Jul 12, 2012·Chemical Communications : Chem Comm·Xiaoding LouZhen Li
Nov 29, 2012·Chemical Society Reviews·Massimo Cametti, Kari Rissanen
Oct 11, 2013·Chemical Society Reviews·Philip A GaleIsabelle L Kirby
Apr 4, 2014·Organic & Biomolecular Chemistry·Arun KumarPalwinder Singh
Jul 7, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Pramod KumarRajeev Gupta
Aug 23, 2012·Organic & Biomolecular Chemistry·Jennifer R HiscockNeil J Wells
Feb 7, 2013·Organic & Biomolecular Chemistry·Claudia CaltagironeGiacomo Picci
Aug 5, 2014·Chemical Communications : Chem Comm·Komala PanduranganThorfinnur Gunnlaugsson
Feb 16, 2021·Frontiers in Chemistry·Utsab MannaMd Alamgir Hossain
Mar 7, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Giacomo PicciClaudia Caltagirone
Apr 4, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Patryk NiedbałaJanusz Jurczak
Oct 31, 2013·Organic Letters·Robert B P ElmesKatrina A Jolliffe
May 23, 2015·Chemical Reviews·Nathalie BusschaertPhilip A Gale
Aug 1, 2013·The Journal of Organic Chemistry·Elaine M BoyleThorfinnur Gunnlaugsson
May 24, 2019·The Journal of Organic Chemistry·Aleksandr S OshchepkovEvgeny A Kataev
Sep 7, 2018·The Journal of Organic Chemistry·Kuppusamy SanthiyaBalasubramanian Murugesapandian

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