A series of symmetrically disubstituted compounds, with substituents linked to the ring through a carbon atom, has been prepared from 2,9-dimethyl-l,lO-phenanthroline. Nmr data are also reported.

The preparation of a series of macrocycles, formed by reaction of HO‐(‐CH2‐CH2‐O‐)nH with 1,10‐phenanthroline‐2,9‐dicarbonyl chloride (n = 2,3,4) and 1,8‐naphthyridine‐2,7‐dicarbonyl chloride (n = 3,4), is described. An improved synthetic route to 2,7‐dimethyl‐1,8‐naphthyridine 9 is also reported.

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The synthesis of nine macrocyclic polyether‐ and polythioether‐diesters 9–13 and dithioesters 14–17 derived from 1,10‐phenanthroline‐2,9‐dicarboxylic acid are reported. The macrocycles were prepared under conditions of high dilution in the absence of metal templates in consistently good yields and their structures were confirmed by 1H and 13C nmr spectroscopy. A macrocyclic phenanthroline‐pyridine tetraester 18 is also recorded.