Synthesis, structure, spectral and coordination properties of a crown ether derivative of 1,3-indandione. A new structural evidence for the versatile reactivity of 2-acetyl-1,3-indandione

Abstract

The current study describes the synthesis of a new 1,3-indandione derivative with conjugated N-phenylaza-15-crown-5 moiety (4). The crystal structure of compound 4 was solved and its optical properties were studied in various solvents and in presence of alkaline and alkaline-earth metal ions. Quantum chemical (DFT) methods were employed to describe the structure and the optical properties of the studied compound and its complexes. The obtained results indicated that the synthesis of compound 4 using acid-catalyzed aldol reaction between 2-acetyl-1,3-indandione and the corresponding aldehyde is accompanied with an unexpected deacetylation step. In this way, the N-phenylaza-15-crown-5 moiety is directly conjugated with the 1,3-indandione fragment, known as a very strong electron acceptor. Therefore, the absorption spectra of 4 are only slightly influenced by complexation with Ba 2+ and Sr 2+ ions.