Synthesis of a coumarin derivative of resorcin[4]arene with solvent-controlled chirality

Anna Szafraniec; Waldemar Iwanek

doi:10.1039/d0ra00368a

Synthesis of a coumarin derivative of resorcin[4]arene with solvent-controlled chirality

RSC Adv. 2020 Mar 30;10(22):12747-12753. doi: 10.1039/d0ra00368a.

Authors

Anna Szafraniec¹, Waldemar Iwanek²

Affiliations

¹ Faculty of Chemistry, Adam Mickiewicz University Uniwersytetu Poznańskiego 8 60-614 Poznań Poland.
² Faculty of Chemical Technology and Engineering, UTP, University of Science and Technology Seminaryjna 3 85-326 Bydgoszcz Poland.

Abstract

This paper presents the synthesis of a coumarin derivative of resorcin[4]arene (1) using a cascade thermolysis/Michael reaction. The influence of the hydrogen bonding system on the conformational rigidity and cyclochirality of the coumarin derivative of resorcin[4]arene was discussed; these properties depended on the proton-donor-acceptor properties of the solvent. Significant differences, which depended on the environment, in the coumarin derivative of resorcin[4]arene fluorescence were observed and discussed.