Polyfunctional Chelate Derivatives of Dinaphthylmethane and Resorcincalix[4]arene: Synthesis and Relationship between Ch
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functional Chelate Derivatives of Dinaphthylmethane and Resorcincalix[4]arene: Synthesis and Relationship between Chelate Structure and Its Acceptor Ability O. S. Serkovaa, A. V. Kamkinaa, I. Yu. Toropyginb, and V. I. Maslennikovaa,* a
Institute of Biology and Chemistry, Moscow State Pedagogical University, Moscow, 129164 Russia b V.N. Orekhovich Research Institute of Biomedical Chemistry, Moscow, 119121 Russia *e-mail: [email protected]; [email protected] Received March 17, 2020; revised March 17, 2020; accepted March 28, 2020
Abstract—Functionalization of methylenebis(naphthalene-2-ol/-2,7-diol) and rccc-resorcincalix[4]arene has given a series of their derivatives at the OH groups with 1, 2, or 4 pairs of chelate ionophore substituents differing in the combination of the constituting electron-donating atoms (O, S , N, P). The effect of the structural features of the ligand on its ability to recognize and bind transition metals cations (Cd2+, Ag+, Hg2+) has been studied by means of liquid extraction. Keywords: methylenebis(naphthalene-2-ol), methylenebis(naphthalene-2,7-diol), resorcincalix[4]arenes, phosphorylation, carbamoylation
DOI: 10.1134/S1070363220080137 Polycyclic aromatic compounds bearing chelate ionophore peripheral groups can be used as extracting agents [1, 2], chemosensors [3–6], ion carriers [7], and building blocks for the creation of complex supramolecular structures [8–9]. Their applications range and efficiency are determined by the nature, number, and spatial arrangement of the ionophore groups as well as the molecule topology. Herein we considered the synthetic routes to the derivatives of methylenebis(naphthalene-2-ol/-2,7-diol) and rccc-resorcincalix[4]arene. The molecules of the synthesized compounds contained 1, 2, or 4 pairs of chelate ionophore groups differing in the combination of the electron-donating atoms (O, S, N, P), those structural features of the ligands were expected to affect the accepting properties towards cations of transition metals (Cd2+, Ag+, Hg2+). Efficiency and selectivity of the metals binding were estimated in the experiments on liquid extraction in the water–chloroform system. The angle between the methylene-bridged naphthalene nuclei in methylenebis(naphthalene-2-ol) 1 and methylenebis(naphthalene-2,7-diol) 2 was determined by the conformation state of the molecules in the solution [10, 11]; the conformation was in its turn dependent on the nature of the solvent and the substituents in positions
2,2ʹ and 7,7ʹ of the naphthalene cycles. Structure and cis/ trans conformation transitions of molecules are shown in Scheme 1. Resorcincalix[4]arenes 3–5 exhibited all-cis configuration of the R substituents in the methylene bridges and took the boat conformation. The boat– crown–boat interconversion (Scheme 2) is typical of such configuration [12–14], the cavity size being thus adjustable to commensurate to different ions size. The interconversion intensity and the benzene fragments deflection from the macrocycle plane depend on the volume and nature of the funct
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