Phosphorylated amino derivatives of thiacalix[4]arene as membrane carriers: synthesis and host–guest molecular recognition of amino, hydroxy and dicarboxylic acids

Abstract

Promising membrane transport and separation systems for selected dicarboxylic, α-hydroxy-and α-amino acids based on thiacalixarene platform have been developed. For the first time, p-tert-butyl thiacalix [4]arenes functionalized at the lower rim with aminophosphonate fragments have been obtained and characterized. As was established by UV-vis spectroscopy, membrane extraction and HPLC, the substitution of amino groups by α-aminophosphonate units significantly enhances the selectivity of host molecules that bind to aspartic and glycolic acids. The aminophosphonate compounds synthesized can be used in the development of sensors and systems employed in the purification and separation of organic acids.

Synthesis of p-tert-butylthiacalix[4]arenes functionalized with tris(2-aminoethyl)amine fragments at the lower rim and their interaction with model lipid membranes

“…The structure of the obtained compounds was characterized by 1 H NMR, 13 C, IR spectroscopy and mass spectrometry (MALDI-TOF).…”

“…The structure and composition of the new thiacalix [4] arene derivatives 4, 5 and 6 were characterized by NMR 1 H, 13 C, IR spectroscopy, mass spectrometry (MALDI-TOF) and elemental analysis.…”

“…Also, tripodal receptors based on a TREN scaffold have been reported to bind nucleotides. [7] Furthermore, natural polyamines [8] as well as synthetic macrocyclic polyamine receptors [9][10][11][12][13] have been shown to effectively and selectively bind nucleotides with some forming supramolecular nanostructures while others successfully transfected cells. [14][15][16] It is obvious that the TREN fragment, a potential receptor unit with several amino groups, takes part in such molecular recognition processes.…”

Calixarenes containing modified meso bridges

“…[22][23][24][25] One should note also heteracalixarenes, i.e. thia-, aza-and homooxa-calixarenes containing S, N and O heteroatoms in their structures, [26][27][28] . They have recently attracted considerable attention due to their easy accessibility and versatile receptor properties.…”

Secondary Amine Derivatives of p-tert-Butyl Thiacalix[4]arenes: Synthesis and Molecular Recognition of Phthalic Acid

“…(Thia)calix[n]arene derivatives are of particular interest as building blocks in the design of synthetic receptors for recognition of cations, anions and neutral molecules. [4][5][6][7][8][9] The possibility of functionalizing the upper and lower rims of (thia)calixarene, [1,[10][11][12][13] and their diverse conformational isomers make (thia)calixarene derivatives attractive for the design of molecular sensors and transmitters, [14] analytical sensors for biomimetic systems [15] and as catalysts. [16] The design of synthetic receptors for dicarboxylic acids [17] is of main interest due to the crucial role that dicarboxylic acids play in the metabolism of living organisms and biotechnology.…”