A [2]catenane containing 1,1′-binaphthyl units and 1,10-phenanthroline fragments:: Synthesis and intermolecular energy transfer processes

A chiral copper (i)-complexed [2]catenane consisting of two interlocking 38-membered rings, each ring incorporating a 2,9-diphenyl-1,10-phenanthroline (dpp) and an (S)-1,1'-binaphthyl group, has been prepared by means of a transition metal template strategy. Demetalation afforded the corresponding free chiral [2]catenane. The coordination polyhedron of the Cu(dpp)(2) core in this chiral copper(i)-complexed [2]catenane reflects the distortion of the chiral 1,1'-binaphthyl units, as evidenced by the circular dichroism (CD) measurements. Emission measurements demonstrated that in the two-chromophore compounds (S)-6 and (S,S)-9, efficient energy transfer between the 1,1'-binaphthyl component and the dpp unit takes place in solution at room temperature. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.