The synthesis and characterization of giant Calixarenes

Vincent Guérineau, Marion Rollet, Stéphane Viel, Bénédicte Lepoittevin, Ludovic Costa, Pascale Saint-Aguet, Régis Laurent, Philippe Roger, Didier Gigmes, Cyril Martini () and Vincent Huc ()
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Vincent Guérineau: Institut de Chimie des Substances Naturelles, CNRS UPR2301, Université Paris-Sud, Université Paris-Saclay
Marion Rollet: CNRS, ICR, UMR7273, 13397, Marseille, France / Institut Universitaire de France
Stéphane Viel: CNRS, ICR, UMR7273, 13397, Marseille, France / Institut Universitaire de France
Bénédicte Lepoittevin: Normandy University
Ludovic Costa: Université Paris-Saclay
Pascale Saint-Aguet: Université Paul Sabatier
Régis Laurent: Université Paul Sabatier
Philippe Roger: Université Paris-Saclay
Didier Gigmes: CNRS, ICR, UMR7273, 13397, Marseille, France / Institut Universitaire de France
Cyril Martini: Université Paris-Saclay
Vincent Huc: Université Paris-Saclay

Nature Communications, 2019, vol. 10, issue 1, 1-14

Abstract: Abstract Calixarenes are cyclic oligomers obtained by condensation of suitable p-functionalised phenols with formaldehyde, usually allowing for the synthesis of the well known small calixarenes (including up to eight phenolic subunits). We report here the discovery of much larger members of this family, exhibiting sizes up to 90 phenolic subunits: the giant calixarenes. These macrocycles are obtained according to simple, easily scalable processes, in yields up to 65%. We show that the formation of these giant macrocycles is favored by an oxygen-containing-group at the para-position of the starting phenol, high concentrations of heavy alkaline bases (rubidium or cesium hydroxides) and long reaction times. A mechanism is proposed to rationalize these observations. These giant macrocycles can also be obtained in the quasi-solid state, opening interesting perspectives in the field of calixarenes chemistry. Along with their intrinsic fundamental interest, these objects are also opening interesting applicative potentialities.

Date: 2019
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DOI: 10.1038/s41467-018-07751-4

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