The highly enantioselective synthesis of helically chiral 1,1'-bitriphenylenes has been achieved via rhodium-catalyzed double [2 + 2 + 2] cycloaddition of biaryl-linked tetraynes with 1,4-diynes (up to 93% ee). Crystal structures and photophysical properties of these helically chiral 1,1'-bitriphenylenes have also been studied.

The convenient synthesis of substituted triphenylenes and azatriphenylenes has been achieved by the cationic rhodium(I)/H8-BINAP or BINAP complex-catalyzed [2 + 2 + 2] cycloaddition under mild conditions. Photophysical properties of representative triphenylenes and azatriphenylenes were examined, which revealed that azatriphenylenes showed higher fluorescence quantum yields than triphenylenes. This method was successfully applied to the synthesis of highly fluorescent triphenylene-based long ladder molecules.

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