Confusion and Neo‐Confusion: Corrole Isomers with an NNNC Core

Fujino, Keitaro; Hirata, Yasuyuki; Kawabe, Yasunori; Morimoto, Tatsuki; Srinivasan, A.; Toganoh, Motoki; Miseki, Yugo; Kudo, Akihiko; Furuta, Hiroyuki

doi:10.1002/ange.201100429

Cited by 46 publications

(35 citation statements)

References 22 publications

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“…The use of intact pyrrole is most favorable because excess amounts can be used readily. In the case of acylation reactions, regular pyrrole and N‐confused pyrrole behave in a similar manner 12. Nevertheless, N‐confused pyrrole showed a higher reactivity than that of regular pyrrole for limited substrates (e.g., Scheme below).…”

Section: Resultsmentioning

confidence: 94%

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Synthesis and Reactivity of 5,10,15‐Triaryl Doubly N‐Confused Bilanes

Toganoh¹,

Gokulnath²,

Kawabe³

et al. 2012

Chemistry A European J

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A series of 5,10,15-tris(pentafluorophenyl) doubly N-confused bilanes were synthesized in a stepwise manner with the aid of sterically demanding N-protecting groups, in which the difference in reactivity between regular pyrrole and N-confused pyrrole plays a crucial role in the synthetic strategy. Some doubly N-confused bilanes were converted into porphyrinoids or a unique 2:2 copper(II) complex with a helical structure. In addition, the conformations and electronic states of the doubly N-confused bilanes were investigated theoretically, giving fruitful information about the effect of confusion on the bilane skeleton.

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Section: Resultsmentioning

confidence: 94%

“…Isomers of NCB, N 2 CB, N 3 CB, and N 4 CB are listed in Scheme with trivial names. Previously, NCB‐(C α ,N,N,N) and NCB‐(N,C α ,N,N) were prepared from N‐confused dipyrromethane for the synthesis of N‐confused corroles and norroles 12. Importantly, this rule can also be applied to higher analogues, such as penta‐ and hexapyrrane.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Reactivity of 5,10,15‐Triaryl Doubly N‐Confused Bilanes

Toganoh¹,

Gokulnath²,

Kawabe³

et al. 2012

Chemistry A European J

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“…The three aromatic states can be interconverted one another using diphyrin(11.1) π‐delocalization triggered by a simple initiator. These original macrocycles belong to the innumerous class of contracted carbaporphyrinoids …”

Section: Methodsmentioning

confidence: 99%

Three‐Stage Aromaticity Switching in Boron(III) and Phosphorus(V) N‐Fused p‐Benziporphyrin

Idec

Pawlicki

Latos‐Grażyński

2018

Chemistry A European J

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Insertion of PCl3 or PhBCl2 into 5,10,15,20‐tetraaryl‐p‐benziporphyrin prompted an intramolecular fusion affording anti‐aromatic phosphorus(V) and non‐aromatic boron(III) complexes of two N‐fused dihydro‐p‐benziporphyrin isomers. These macrocycles are classified as carbatriphyrin due to the common [CNN] coordination. A sequence of direct transformations, triggered by protonation or two‐electron redox processes, afforded a set of three mutually convertible N‐fused p‐benziporphyrinoids, with distinct anti‐aromatic, non‐aromatic, and aromatic spectroscopic features.

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“…In the benzonorrole monomer 9, absorption maxima are observed at l = 611 and 645 nm, which are slightly shorter than those of the parent norrole (l = 618 and 659 nm). [6] The absorption maximum of BNdimerH 2 (l = 633 nm) is comparable to that of 9, thus suggesting the weak interaction between two benzonorrole units in BNdimerH 2 . Contrastingly, a remarkable red shift is observed in cis-BNdimer and its absorption maximum reaches up to l = 845 nm.…”

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confidence: 91%