Issue 5, 2014

Synthesis and characterization of spin-labelled [2]rotaxanes containing tetrathiafulvalene and 1,5-dioxynaphthalene molecular stations

Abstract

The central component of one of the most studied programmable molecular switches reported by Stoddart and Heath is a [2]rotaxane, which consists of a cyclobis(paraquat-p-phenylene) shuttle (CBPQT4+)(PF6)4 (the ring) encircling a finger and moving between two molecular stations, tetrathiafulvalene (TTF) and 1,5-dioxynaphthalene (DNP). In order to employ ESR spectroscopy for understanding the mechanism of this switch, we report here the synthesis and characterization of [2]rotaxanes having persistent nitroxide radicals as the stopper units and TTF or DNP as molecular stations. Isolation of the rotaxanes was successful when bulky nitroxide radicals containing cyclohexyl substituents at 2 and 6 positions of the piperidine-N-oxyl ring were used as terminal stoppers.

Graphical abstract: Synthesis and characterization of spin-labelled [2]rotaxanes containing tetrathiafulvalene and 1,5-dioxynaphthalene molecular stations

Supplementary files

Article information

Article type
Research Article
Submitted
05 mar 2014
Accepted
27 mar 2014
First published
27 mar 2014

Org. Chem. Front., 2014,1, 477-483

Synthesis and characterization of spin-labelled [2]rotaxanes containing tetrathiafulvalene and 1,5-dioxynaphthalene molecular stations

R. Manoni, F. Romano, C. Casati, P. Franchi, E. Mezzina and M. Lucarini, Org. Chem. Front., 2014, 1, 477 DOI: 10.1039/C4QO00065J

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