Molecular Signal Transduction by Conformational Transmission: Use of Tetrasubstituted Perhydroanthracenes as Transducers

Abstract

2,3,6,7-Tetrasubstituted cis-anti-cis perhydroanthracenes have been studied as conformational transducers for molecular signal transduction. 2,2'-Bipyridine groups attached to the perhydroanthracene through ether linkages were chosen as receptor substituents, while pyrene groups were selected as effectors. A chelation-induced triple ring flip of the perhydroanthracene could be achieved by the complexation of zinc(II) ions at the bipyridine sites of ligands 13 and 15. It was found that two pyrene substituents attached to the perhydroanthracene via a linker with an E double bond and an ester group could be used to monitor the triple ring flip. In the equatorial positions, the pyrenes are sufficiently close to form an excimer in the excited state, giving a fluorescence signal at 480 nm. In the axial positions, they are far away from each other and give mainly a monomer fluorescence signal at 380 nm. Both the bipyridine receptor and the pyrene effector are present in compound 33. The conformational switching 34-->35 (the two conformers of 33) has successfully been used for a signal transduction over a signal distance of 2 nm.