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The condensation reaction of 1,10-phenanthroline-5,6-dione with N,N'-bis(2aminophenyl)ethylenediamine in a 1:1 molar ratio produces the tetracyclic gem-cis-bis(aminal) 7a,12c-(2,2'-bipyridin-3,3'-diyl)-1,2,7a,12c-tetrahydro-7H,8H-2a,7,8,12btetraazacyclopenta(fg)tetracene methanol (1:1) (1) (Figure 1). The X-ray crystal structure of (1)·MeOH (Figure 3) shows the molecule to be non-planar and chiral, and comprising three sixmembered rings and one five-membered ring fused onto the back of a bipyridine moiety. Reaction of the dione with selected non-aromatic polyamines affords only 1,10-phenanthroline5,6-diol.

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Synthesis and X-ray crystal structure of a tetracyclic gem-cis-bis(aminal) formed from N,N'-bis(2-aminophenyl)ethylenediamine and 1,10-phenanthroline-5,6-dione