6,7-Bis(alkyloxy)-2,3-dihydrophthalazine-1,4-diones self-assemble into lactim-lactam trimeric disks in solution as demonstrated by SEC and NMR. With suitable substituents, as in Phthal8, Phthal12, and Phthal16, these disks self-organize into a thermotropic, columnar, discotic phase. The disubstituted phthalhydrazide unit thus represents a general motif for the recognition-induced generation of supramolecular, discotic liquid crystals by self-assembly.

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Chiral supermolecules may be obtained from suitable achiral molecular constituents associated through a dissymmetrizing interaction mode. This is the case for the supermolecules I-IV formed by hydrogen-bonding association between the achiral complementary components la, b and Za,b,c. The crystal structures of the supermolecular pairs 1-111 and of the homochiral aggregate of two ternary supermolecules IV have been determined. The structural data are discussed.

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