A tri(ethylene glycol)-tethered Morita-Baylis-Hillman dimer in the formation of macrocyclic crown ether-paracyclophane hybrid structures

Mario Saletti; Jacopo Venditti; Marco Paolino; Arianna Zacchei; Germano Giuliani; Gianluca Giorgi; Claudia Bonechi; Alessandro Donati; Andrea Cappelli

doi:10.1039/d3ra06792k

A tri(ethylene glycol)-tethered Morita-Baylis-Hillman dimer in the formation of macrocyclic crown ether-paracyclophane hybrid structures

RSC Adv. 2023 Dec 11;13(51):35773-35780. doi: 10.1039/d3ra06792k. eCollection 2023 Dec 8.

Authors

Mario Saletti¹, Jacopo Venditti¹, Marco Paolino¹, Arianna Zacchei¹, Germano Giuliani¹, Gianluca Giorgi¹, Claudia Bonechi¹, Alessandro Donati¹, Andrea Cappelli¹

Affiliation

¹ Dipartimento di Biotecnologie, Chimica e Farmacia, Università di Siena Via A. Moro 2 53100 Siena Italy andrea.cappelli@unisi.it +39 0577 232416.

Abstract

A Morita-Baylis-Hillman acetate was dimerized by a click-chemistry Copper(i)-Catalysed Azide-Alkyne Cycloaddition (CuAAC) reaction employing a tri(ethylene glycol) diazide derivative to obtain a dimeric MBHA derivative. The reaction of this dimeric MBHA derivative with n-butylamine afforded a photoisomerizable macrocyclic crown ether-paracyclophane hybrid architecture that is potentially useful in a large variety of applications as well as those already well-known for crown ethers.