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Doubly N-confused and ring-contracted [24]hexaphyrin Pd-complexes as stable antiaromatic N-confused expanded
Fuying Luo1, Le Liu1, Han Wu1
1Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, 410081, Changsha, China.
Abstract:
As isomers of the regular porphyrins, N-confused porphyrins have attracted extensive attention of chemists because of their unique chemical structures, chemical reactivities, and physical properties, which result in their promising applications in the fields of catalytic chemistry, biochemistry and material science. Typically, N-confused porphyrins are synthesized via acid catalyzed condensation and following oxidation during which lactams are often formed as the byproducts. Here we report doubly N-confused and ring-contracted [24]hexaphyrin(1.1.0.1.1.0) mono- and bis-Pd-complexes as stable antiaromatic N-confused expanded porphyrins, which are synthesized through Pd-catalyzed Suzuki-Miyaura coupling of 1,14-dibromotripyrrin. These macrocycles show a paratropic ring currents, an ill-defined Soret band, a red-shifted weak absorption tail, and a small HOMO-LUMO gap. NBS bromination of the bis Pd-complex give its mono- and dibromides regioselectively, which are effectively used to synthesize a [24]hexaphyrin dimer and a NiII porphyrin-[24]hexaphyrin-NiII porphyrin triad, respectively.
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