Preorganized Fluorescent Receptor for the Preferential Binding of the Glutarate Anion. Issue 22 (18th July 2016)

• Record Type: Journal Article
• Authors: Más‐Montoya, Miriam; Curiel, David; Ramírez de Arellano, Carmen; Tárraga, Alberto; Molina, Pedro
• Is Part Of: European journal of organic chemistry. Issue 22(2016)
• Page Start: 3878
• Page End: 3883
• Publication Date: 2016-07-18
• Subjects: Molecular recognition -- Sensors -- Luminescence -- Nitrogen heterocycles -- Carboxylic acids; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600521
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A carbazolo[1, 2‐ a ]carbazole‐2, 11‐dicarboxamide has been synthesized and studied as a dicarboxylate anion receptor. The preorganized structure of this ligand affords a size‐selective response when a homologous series of dicarboxylates are analyzed. The structural correlation between the receptor and the different dianions was confirmed by 1 H NMR studies, and different binding modes were also studied by X‐ray crystal structure analysis. The fluorescent properties of the carbazolocarbazole unit give a ratiometric response for those anions that have the best size fit. During the recognition process, the selective signaling of the glutarate anion results in a switch in the fluorescence color between the free and bound species. The detection of glutarate metabolites is important for the diagnosis of glutaric aciduria. Abstract : A carbazolo[1, 2‐ a ]carbazole‐2, 11‐dicarboxamide was employed as a dianion receptor that affords a size‐selective response when a homologous series of dicarboxylates are analyzed. Interestingly, a preferential ratiometric fluorescent response was observed for the glutarate anion during the recognition process, which produced an evident color change in the emitted light.