Neo‐Confused Porphyrins, a New Class of Porphyrin Isomers

Abstract

Confused yet still diatropic: A new type of porphyrin isomer is reported where a pyrrole nitrogen is connected to one of the meso‐bridges. This system retains porphyrin‐like characteristics and reacts with nickel(II) acetate to generate a stable organometallic complex.

Macrocyclic Transformations from Norrole to Isonorrole and an N‐Confused Corrole with a Fused Hexacyclic Ring System Triggered by a Pyrrole Substituent

“…[4] To address this issue,w ee nvision that a" confusion approach" [5] can be systematically applied to obtain new electronic structures by varying the linking modes of pyrrolic subunits,f or example C a À C b , [6] [7] or N À C a [6c,8] ( Figure 1). [8] Notably,these compounds retain 18-p-electron conjugated circuits,a nd their resultant properties,s uch as extended UV/Vis absorption, tunable aromaticity,a nion-binding ability,c ation complexation, and oxidative coupling reactivity of the inner carbon atom, have been thus demonstrated. [8] Notably,these compounds retain 18-p-electron conjugated circuits,a nd their resultant properties,s uch as extended UV/Vis absorption, tunable aromaticity,a nion-binding ability,c ation complexation, and oxidative coupling reactivity of the inner carbon atom, have been thus demonstrated.…”

Expanded Porphyrins: More Confusion All the Time

“…[5] In 2011, Furuta and co-workers reported the first example of at etrapyrrolic macrocycle containing aC À Nlinked bipyrrole unit, which was named norrole. [6] In the same year,L ash et al reported neo-confused porphyrin, [7] which also contains an N-linked pyrrole.I tc an be regarded as another important new class of porphyrin isomers. [7] Expanding the macrocycle size of porphyrins is another important approach for developing novel porphyrinoids,such as hexaphyrin.…”

“To Twist or Not to Twist”: Figure‐of‐Eight and Planar Structures of Octaphyrins

“…This approach was previouslye xplored by Osuka and co-workers to maintain ap lanar macrocycle (30), but it fell short of ac ompletely conjugated system. [25] In an analogous synthetic method, bithiophened iol 54 was condensed with 1,4-phenylbis(dipyrromethane) (28), followed by oxidation with DDQ (Scheme 21). [37] The resulting macrocycle was identified as 34 p octaphyrin 55,w hichc ontained ap henylene bridge at the center of the macrocycle.…”