Thiahexaphyrinone and thia-dipyrrin-appended corrorin have been synthesized. Surprisingly, further oxidation of compound with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in dichloromethane afforded dimer with two molecules of compound linked at the α-carbon atoms of the thienyl units. Treatment of compound with DDQ in MeOH and SnCl in tetrahydrofuran/HO afforded the dimethoxy-attached dimer and hydrogenated dihydroxy-attached dimer , respectively. These results provide the first examples for synthesizing thiophene-linked porphyrinoid dimers with tunable near-infrared absorption and chirality.
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