In summary, a facile synthetic strategy involving Bi(OTf)3-catalyzed cyclization reaction of vinyl ethers was developed for the synthesis of a series of expanded helicenes in a nearly "one-pot" mode. The obtained helical polyarenes contain up to 35 cata-fused benzene rings which represent a record for helicenes and expanded helicenes. Notably, enantiopure H2, H3, and H4 can be isolated, and they all show strong chiroptical responses with relatively large |gabs| values (up to 0.024). Further improvement of both dissymmetric factors as well as fluorescence quantum yield is possible by adjusting the building blocks and molecular symmetry via the same synthetic method.