Active-metal template clipping synthesis of novel [2]rotaxanes

Cătălin C Anghel; Teodor A Cucuiet; Niculina D Hădade; Ion Grosu

doi:10.3762/bjoc.19.130

Active-metal template clipping synthesis of novel [2]rotaxanes

Beilstein J Org Chem. 2023 Nov 20:19:1776-1784. doi: 10.3762/bjoc.19.130. eCollection 2023.

Authors

Cătălin C Anghel^{1

2}, Teodor A Cucuiet¹, Niculina D Hădade¹, Ion Grosu¹

Affiliations

¹ Babeș-Bolyai University, Faculty of Chemistry and Chemical Engineering, Supramolecular Organic and Organometallic Chemistry Centre, 11 Arany Janos Str., RO-400028-Cluj-Napoca, Romania.
² University of Bucharest, Faculty of Chemistry; Department of Organic Chemistry, Biochemistry and Catalysis, Research Centre of Applied Organic Chemistry, 90-92 Panduri Street, RO-050663 Bucharest, Romania.

Abstract

Mechanically interlocked molecules (MIMs) have been important synthetic targets in supramolecular chemistry due to their beautiful structures and intriguing properties. We present herein a new synthetic strategy to access [2]rotaxanes, namely active-metal template clipping. We discuss the design of the target [2]rotaxanes, synthesis and characterization of the axle, macrocycle precursors and macrocycles as well as preparation of the final [2]rotaxanes by active template copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) as key step of the synthesis. HRMS and NMR experiments have been performed to confirm the formation of the interlocked structures.

Keywords: [2]rotaxanes; active-metal template; clipping; copper(I)-catalyzed alkyne–azide cycloaddition; mechanically interlocked structures.

Grants and funding

Financial support by Romanian National Authority for Scientific Research and Innovation, CNCS-UEFISCDI, projects numbers PN-III-P4-ID-PCCF-2016-0088 and PN-III-P4-PCE-2021-1812, is gratefully acknowledged.