The rhodium-catalyzed dehydrogenative coupling of N-pyridylindoles with alkynes proceeds smoothly through rollover cyclometalation to produce indolo[1,2-a][1,8]naphthyridine derivatives. A number of tetra-, penta-, and hexacyclic N-containing heteroaromatics can also be readily constructed in a similar manner. The L-shaped π-conjugated molecules exhibit intense solid-state fluorescence.
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Morioka et al. (2015) studied this question.