Synthesis and chiroptical property of C2-symmetric cyclohexapyrrole

Condensation reaction of gem-dimethyldipyrrylmethane-5,5′-dicarbinol and 4,4′-dimethyl-3,3′-di-iso-butyl-2,2′-bipyrrole under the catalysis by trifluoroacetic acid gave a hexapyrrolic macrocycle 6 in 15% yield after DDQ oxidation. X-ray crystallography of 6 shows that three parts of highly planar dipyrrylmethene unit are assembled by two sp3 hybridized gem-dimethyl carbon bridges and one direct linking at the pyrrole α-positions, leading to C2 molecular symmetry. The complexation of 6 with (S)-(+)- and (R)-(−)-mandelic acid induced a CD Cotton effect at 461 and 650 nm.