Copper(II) carboxylate tetramers formed from an enantiopure ligand containing a π-stacking supramolecular synthon: single-crystal to single-crystal enantioselective ligand exchange.

An enantiopure ligand built from connecting the π···π stacking 1,8-naphthalimide supramolecular synthon with L-asparagine, L(asn)(-), forms tetrameric [Cu(4)(L(asn))(8)(py)(MeOH)]. The methanol ligand, located in a chiral pocket, is replaced enantioselectively when exposed to racemic ethyl lactate vapor to yield [Cu(4)(L(asn))(8)(py)((S)-ethyl lactate)], in a single-crystal to single-crystal gas/solid transformation.