Abstract: Highlights • Fluorinated diaminooxacalixarenes are formed by the reaction of the corresponding dinitrooxacalixarenes with sodium dithionite. • Tetraoxacalix[4]arenes with nitro and amino groups in the inner rim exist in solution as an equilibrium mixture of conformers with 1,3-alternate and "chair" structure. • For fluorinated tetraoxacalixarenes with amino groups in the inner rim, the 1,3-alternate structure is more preferable to the "chair" structure. • The position of conformational equilibrium of tetraoxacalixarenes with nitro groups in the inner rim depends on the polarity of the solvent. Abstract Polyfluorinated diaminotetraoxacalixarenes and diaminobicyclooxacalixarene were obtained in good yield by reduction of the corresponding dinitrooxacalixarenes with sodium dithionite. Fluorinated tetraoxacalix[4]arenes with nitro and amino groups located in the inner rim of the macrocycle exists in the solution as an equilibrium mixture of two conformers. For diaminotetraoxacalixarenes the conformational equilibrium is shifted towards conformers having a 1,3-alternate structure. The ESI-MS method shows the possibility of complexing fluorinated diaminotetraoxacalixarenes and diaminobicyclooxacalixarenes with metal cations.

Cite: Han H. , Kovtonyuk V.N. , Gatilov Y.V. , Andreev R.V. , Nefedov A.A.
Fluorinated diaminobicyclooxacalixarene and diaminotetraoxacalixarenes: Synthesis and conformational behaviour
Journal of Fluorine Chemistry. 2024. V.273. P.110235. DOI: 10.1016/j.jfluchem.2023.110235 WOS OpenAlex

Dates:

Submitted:	Oct 19, 2023
Accepted:	Nov 30, 2023
Published online:	Dec 7, 2023
Published print:	Jan 1, 2024

Identifiers:

Web of science:	WOS:001133079900001
OpenAlex:	W4389469683

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