New chromogenic and fluorescent probes for anion detection: formation of a [2 + 2] supramolecular complex on addition of fluoride with positive homotropic cooperativity

The Journal of Organic Chemistry
Chan-Yu ChenShih-Sheng Sun

Abstract

Two new chromogenic and fluorescent probes for anions have been designed, synthesized, and characterized. These probes contain multiple hydrogen bonding donors including hydrazine, hydrazone, and hydroxyl functional groups for potential anion interacting sites. Despite the possible flexible structural framework due to the presence of sp3 carbon linkage, X-ray structure analysis of probe 2 displayed an essentially planar conformation in the solid state owing to strong crystal packing interactions comprising a combination of favorable pi-pi stacking effect and hydrogen bonding to cocrystallized CH3OH molecules. Both probes 1 and 2 display orange color in DMSO solution and show fairly weak fluorescence at room temperature. Binding studies revealed that both probes 1 and 2 show noticeable colorimetric and fluorescent responses only to F-, OAc-, and H2PO4- among the nine anions tested (F-, Cl-, Br-, I-, OAc-, H2PO4-, HSO4-, ClO4-, and NO3-). The general trend of the sensitivity to anions follows the order of F- > OAc- > H2PO4- > Cl- > Br- approximately I- approximately HSO4- approximately ClO4- approximately NO3-. A 1:2 (probe to anion) binding stoichiometry was found for probe 1 with OAc- and H2PO4- and probe 2 with F-, OAc-, and H...Continue Reading

References

Apr 12, 2002·Proceedings of the National Academy of Sciences of the United States of America·Lagili O AbouderbalaKarl J Wallace
Aug 17, 2002·The Journal of Organic Chemistry·Joseph Raker, Timothy E Glass
Nov 7, 2002·Journal of the American Chemical Society·Jonathan L SesslerHiroyuki Furuta
Jan 30, 2003·Journal of the American Chemical Society·Pall ThordarsonAlan E Rowan
Nov 13, 2003·Chemical Reviews·Ramón Martínez-Máñez, Félix Sancenón
Apr 22, 2004·Journal of the American Chemical Society·Chantelle R BondyStephen J Loeb
Jun 10, 2004·Chemical Reviews·Larisa Kovbasyuk, Roland Krämer
Sep 15, 2004·Angewandte Chemie·Pall ThordarsonRoeland J M Nolte
Dec 17, 2004·Journal of the American Chemical Society·Massimo BoiocchiEnrico Monzani
Feb 11, 2005·Journal of the American Chemical Society·Nathan C GianneschiChad A Mirkin
Jul 2, 2005·The Journal of Organic Chemistry·David Esteban-GómezMaurizio Licchelli
Sep 8, 2005·Journal of the American Chemical Society·Hidekazu MiyajiChang-Hee Lee
Oct 21, 2005·Organic Letters·Pavel AnzenbacherManuel Marquez
Dec 17, 2005·The Journal of Organic Chemistry·Thorfinnur GunnlaugssonGillian M Hussey
Jan 27, 2006·Organic Letters·Ryuhei Nishiyabu, Pavel Anzenbacher
Feb 14, 2006·The Journal of Organic Chemistry·David R TurnerJonathan W Steed
Feb 24, 2006·Organic Letters·Maurizio LicchelliAntonio Poggi
May 17, 2006·Accounts of Chemical Research·Valeria AmendolaMaurizio Licchelli
Jun 1, 2006·Journal of the American Chemical Society·Emilio M PérezNazario Martín

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Citations

Jul 19, 2011·Chemical Communications : Chem Comm·Hiromitsu MaedaYohei Haketa
Mar 1, 2012·Chemistry : a European Journal·Pengchong XueHirotaka Ihara
May 30, 2013·Chemical Communications : Chem Comm·Ashutosh S Singh, Shih-Sheng Sun
Dec 14, 2018·ChemistryOpen·Sandeep Kumar DeySheshanath V Bhosale
Oct 19, 2010·Analytical Sciences : the International Journal of the Japan Society for Analytical Chemistry·Yamin LiWeiping Xu
Mar 26, 2014·Chemical Reviews·Ying ZhouJuyoung Yoon

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