1,10-(1-H-IMIDAZOL-5-YL)DECANEPHOSPHONIC ACID: A NEW COMPOUND WITH BASIC AND ACIDIC SITES TO FABRICATE PROTON-CONDUCTING SOLID ELECTROLYTES |
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Authors: | Enzo Montoneri Maria C. Gallazzi Chiara Bertarelli Roberto Gobetto Luca Salassa |
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Affiliation: | 1. Dipartimento di Chimica Generale ed Organica Applicata , Torino, Italy;2. Dipartimento di Chimica, Materiali e Ingegneria Chimica “G. Natta,” Politecnico di Milano , Milano, Italy;3. Dipartimento di Chimica I.F.M. , Torino, Italy |
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Abstract: | 2-(tert-butyldimethylsilyl)-5-(10-bromodecyl)-1-(N,N-dimethylsulfamoyl)-imidazole and NaPO3 Et2 react at room temperature to yield the corresponding imidazole diethyl phosphonate, which when refluxed with concentrated HBr yields 1,10-(1-H-imidazol-5-yl)decanephosphonic acid hydrobromide (VI). Compound VI titrated with the required mole equivalents of NaOH yields 1,10-(1-H-imidazol-5-yl)decanephosphonic acid (VII) and 1,10-(1-H-imidazol-5-yl)decane (sodium)phosphonates (VIII). CP-MAS NMR (13C, 31P, and 15N) and IR spectroscopy indicate that only compound VII is likely to yield a polymeric structure where each phosphonic acid group is H bonded to the imidazole ring of the same molecule and to the imidazole ring of another molecule. For this reason, solid-state proton conductivity in VII is likely to be favored. |
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Keywords: | 1,10-(1-H-imidazol-5-yl)-decanephosphonic acid imidazole phosphonic acids solid proton conductors |
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