The development of new synthetic methods for the monoalkylation of calix[4]arenes at the lower rim allows the synthesis of a new class of trihydroxamate siderophores. Three chelating hydroxamic acid units are introduced through a sequence of reactions which blocks the macrocycle in the cone conformation. The new ligands obtained form neutral 1 :1 complexes (FeL) with iron (III), which are stable in EtOH/H,O 9: 1 at pH 2-7. Calix[4]arene his-crown ethers are prepared by exploiting the selective 1,2-(proximal) functionalization of calix[4]arenes at the lower rim. These ligands are, however, less effective in complexing alkali metal cations compared with the 1J-calix [4] arene crown-ethers which, in their partial cone structure, offer a better shielding for the complexed cations. Rigid upper rim-bridged calix [4] arenes potentially useful for the inclusion of neutral molecules are prepared by exploiting the selective 1,3- diformylation of calixC4larene at the upper rim. Finally a new chloromethylation method for calix 141 arenes blocked in the cone conformation is described together with the synthesis of new cavitands.

New Artificial Receptors from Selectively Functionalized Calix[4]arenes / Arduini, Arturo; Casnati, Alessandro; Fabbi, M.; Minari, P.; Pochini, Andrea; Sicuri, A. R.; Ungaro, Rocco. - In: SUPRAMOLECULAR CHEMISTRY. - ISSN 1061-0278. - 1:(1993), pp. 235-246.

New Artificial Receptors from Selectively Functionalized Calix[4]arenes

ARDUINI, Arturo;CASNATI, Alessandro;POCHINI, Andrea;UNGARO, Rocco
1993

Abstract

The development of new synthetic methods for the monoalkylation of calix[4]arenes at the lower rim allows the synthesis of a new class of trihydroxamate siderophores. Three chelating hydroxamic acid units are introduced through a sequence of reactions which blocks the macrocycle in the cone conformation. The new ligands obtained form neutral 1 :1 complexes (FeL) with iron (III), which are stable in EtOH/H,O 9: 1 at pH 2-7. Calix[4]arene his-crown ethers are prepared by exploiting the selective 1,2-(proximal) functionalization of calix[4]arenes at the lower rim. These ligands are, however, less effective in complexing alkali metal cations compared with the 1J-calix [4] arene crown-ethers which, in their partial cone structure, offer a better shielding for the complexed cations. Rigid upper rim-bridged calix [4] arenes potentially useful for the inclusion of neutral molecules are prepared by exploiting the selective 1,3- diformylation of calixC4larene at the upper rim. Finally a new chloromethylation method for calix 141 arenes blocked in the cone conformation is described together with the synthesis of new cavitands.
New Artificial Receptors from Selectively Functionalized Calix[4]arenes / Arduini, Arturo; Casnati, Alessandro; Fabbi, M.; Minari, P.; Pochini, Andrea; Sicuri, A. R.; Ungaro, Rocco. - In: SUPRAMOLECULAR CHEMISTRY. - ISSN 1061-0278. - 1:(1993), pp. 235-246.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/1498699
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