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.
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