Bispyrrolotetrathiafulvalene-containing [2]catenanes

Michael R Tomcsi; J Fraser Stoddart

doi:10.1021/jo701374b

Bispyrrolotetrathiafulvalene-containing [2]catenanes

J Org Chem. 2007 Nov 23;72(24):9335-8. doi: 10.1021/jo701374b. Epub 2007 Oct 30.

Authors

Michael R Tomcsi¹, J Fraser Stoddart

Affiliation

¹ California Nanosystems Institute and Department of Chemistry and Biochemistry, University of California Los Angeles, Los Angeles, CA 90095, USA.

PMID: 17967033
DOI: 10.1021/jo701374b

Abstract

Two [2]catenanes incorporating bispyrrolotetrathiafulvalene (BPTTF) and weaker aryl donors, hydroquinone (HQ) and 1,5-dioxynaphthalene (DNP), respectively, have been prepared and characterized. These [2]catenanes show a predominant amount (>95:5) of the co-conformation in which either the HQ or the DNP unit is encircled by a tetracationic cyclophane, cyclobis(paraquat-p-phenylene) (CBPQT4+), contrary to what is observed in systems based on the parent tetrathiafulvalene (TTF). These new [2]catenanes act effectively as molecular switches which are always configured in the "on" state.