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Synthesis of a symmetrical tris-tetrazole as isostere of a tricarboxylic acid: behind new tridentate ligands for MOFs
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Academic Editor: Julio A. Seijas
Published:
14 November 2021
by MDPI
in The 25th International Electronic Conference on Synthetic Organic Chemistry
session General Organic Synthesis
Abstract:
The synthesis and characterization of three tridentate ligands for new MOFs is described. A triple aminolysis of the 1,3,5-tribenzoyl chloride with p-aminobenzoic acid gave the tricarboxylic acid 1 in 90% yield. Moreover, the same reaction, also from the 1,3,5-tribenzoyl chloride, but using p-aminobenzonitrile gave the new tris-benzonitrile 2 in 85% yield. Finally, this later one was treated with sodium azide and a Lewis acid to synthesize the also new tris-tetrazole-based ligand 3 in 72% yield through a [3+2] azide-nitrile cycloaddition. It is noteworthy that the isosterism between carboxylic acids and tetrazoles may be considered to design and fabricate new MOFs with expected similar properties.
Keywords: Metal-Organic Frameworks (MOFs); tridentate ligands; tricarboxylic acids; tris-benzonitriles; tris-tetrazoles; aminolysis
