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Experimental confirmation of proton conductivity predicted from intermolecular hydrogen-bonding in spatially-confined novel histamine derivatives

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Abstract The new compounds with one (N-(2-(1H-imidazol-4-yl)ethyl)benzamide; A1), two (N,N′-bis(2-(1H-imidazol-5-yl)ethyl)terephthalamide; A2) and three (N,N′,N′′-tris(2-(1H-imidazol-5-yl)ethyl)benzene-1,3,5-tricarboxamide; A3) histamine units were synthesized with an expectation of the realization of high proton conductivity in… Click to show full abstract

Abstract The new compounds with one (N-(2-(1H-imidazol-4-yl)ethyl)benzamide; A1), two (N,N′-bis(2-(1H-imidazol-5-yl)ethyl)terephthalamide; A2) and three (N,N′,N′′-tris(2-(1H-imidazol-5-yl)ethyl)benzene-1,3,5-tricarboxamide; A3) histamine units were synthesized with an expectation of the realization of high proton conductivity in a high temperature region in the presence of imidazole groups. The X-ray crystal structure analysis revealed the network structures of the strong intra- and intermolecular hydrogen bonds. The thermal degradation temperatures were much higher than those for the original histamine. The proton conductivities of the single crystals were measured in a wide temperature range. The results of these three compounds were shown at different temperatures. Referring to the crystal structure, the water molecules are confined in a local position and the protons cannot spread freely over the whole crystal lattice. In this way, the information from X-ray analyzed crystal structure allowed us to predict the proton transfer behaviors of these compounds, which were confirmed by performing the proton conductivity experiment.

Keywords: proton conductivity; intermolecular hydrogen; histamine; proton

Journal Title: Journal of Solid State Chemistry
Year Published: 2021

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