DBS‐Based Eutectogels: Organized Vessels to Perform the Michael Addition Reaction**

Author:

Rizzo Carla1,Marullo Salvatore1,Benaglia Maurizio2,D'Anna Francesca1

Affiliation:

1. Università degli Studi di Palermo Dipartimento STEBICEF Sezione di Chimica Viale delle Scienze, Ed. 17 90128 Palermo Italy

2. Università degli Studi di Milano Dipartimento di Chimica Viale Golgi 19, Corpo C 20133 Milano Italy

Abstract

AbstractSupramolecular eutectogels were obtained from the gelation of 1,3 : 2,4‐dibenzylidene‐D‐sorbitol (DBS) in cholinium chloride‐based deep eutectic solvents (DES), differing for the nature of the hydrogen bond donor. Ethylene glycol, diethylene glycol, triethylene glycol, glycerol and urea were tested. Soft materials were fully characterized, determining critical gelation concentration, gel‐sol transition temperatures and mechanical properties. Furthermore, to have information about the organization of the gelator in the tridimensional network, resonance light scattering, circular dichroism and microscopy investigations were performed. Eutectogels were used as organized “vessels” to perform the L‐proline catalyzed Michael addition reaction. The probe reaction was carried out in gel phase and in DES solution. Data collected shed light on the effect that gel microenvironment exerts on the outcome of the reaction. In general, gel phases allowed having comparable or even better results than the ones collected in DES solution, with better results obtained in soft materials with the highest organization, as accounted for by the presence of larger aggregates and the occurrence of stronger intermolecular interactions. In turn, this accounts also for the effect of substrates structure that indicates that better yields could be obtained in the presence of more flexible nucleophile and dienones, having more extended π‐surface.

Funder

Università degli Studi di Palermo

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry

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