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A [2]Catenane Containing 1,1′‐Binaphthyl Units and 1,10‐Phenanthroline Fragments: Synthesis and Intermolecular Energy Transfer Processes
Author(s) -
Koizumi Masatoshi,
DietrichBuchecker Christiane,
Sauvage JeanPierre
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300572
Subject(s) - catenane , chemistry , phenanthroline , chromophore , intermolecular force , copper , circular dichroism , ring (chemistry) , crystallography , stereochemistry , polymer chemistry , photochemistry , molecule , organic chemistry
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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)