Novel furan-, thiophene- and benzo[b]thiophene bridged macrocycles of 4,4′-bipyridine

Add time:07/12/2019    Source:sciencedirect.com

Eight novel heterocyclic bridged phanes of the paraquat type were synthesized by a simple two-step procedure. Starting from furan bridged bis(4,4′-bipyridinium) dication 2 and the corresponding bis(bromomethyl)arenes furanophanes of 4,4′-bipyridine were obtained in moderate to high yields. In similar manner thiphenophane 9 was synthesized in low yield using dication 8 as precursor. The spectroscopic properties of furanophane 4 and thiophenophane 9 were compared. Cycloadditions on the furan ring failed, which is attributed to the decrease of electron density of the furan ring caused by neighbouring electron-accepting bipyridinium groups. The syntheses of the benzo[b]thiophene bridged phanes were performed starting from dibromide 10 and bis(4,4′-bipyridinium) dications 12–14 since the instability of the required bis(4,4′-bipyridinium) dication 11 did not allow its use in aqueous solution.

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