Regulation of NH-tautomerism in N-confused porphyrin by N-alkylation.

@article{Toganoh2012RegulationON,
  title={Regulation of NH-tautomerism in N-confused porphyrin by N-alkylation.},
  author={Motoki Toganoh and Takaaki Yamamoto and Takayoshi Hihara and Hisanori Akimaru and Hiroyuki Furuta},
  journal={Organic \& biomolecular chemistry},
  year={2012},
  volume={10 22},
  pages={
          4367-74
        }
}
A variety of internally N-alkylated N-confused porphyrins were prepared in a stepwise manner through the protection of the reactive peripheral nitrogen atom. NH-Tautomerism in N-confused porphyrins was found to be regulated by N-alkylation, which enabled us to obtain discrete information on two important NH-tautomers of an N-confused porphyrin. 
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11 Citations

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Rhenium complexes of peripherally π-extended N-confused porphyrins
Peripherally π-extended N-confused porphyrin rhenium complexes were synthesized by the rhenium-mediated reactions of N-confused porphyrins with 2-methyl azaarene and the structures were elucidated by…
NH Tautomerism of N-Confused Porphyrin: Solvent/Substituent Effects and Isomerization Mechanism.
TLDR
The mechanism of isomerization is identified as an intramolecular process including the rotation of the confused pyrrole in pyridine/ chloroform and DMF/chloroform mixed solvent systems, and as a pyrsidine-mediated process in p Pyridine alone.
Thiophene-fused dithiaoctaphyrins: π-system switching between cross-conjugated and macrocyclic π-networks.
We synthesized for the first time octaphyrins with a dithieno[3,4-b:3',4'-d]thiophene core as thiophene-fused dithiaoctaphyrins with a cross-conjugated structure. The octaphyrins revealed…
N-Fused Porphyrin: A Maverick Member of the Porphyrin Family
Fusion is a relatively new concept to produce unique members of the porphyrin family. A representative compound formed by fusion is N-fused porphyrin, which is synthesized from N-confused porphyrin...
Creation from Confusion and Fusion in the Porphyrin World─The Last Three Decades of N-Confused Porphyrinoid Chemistry.
Confusion is a novel concept of isomerism in porphyrin chemistry, delivering a steady stream of new chemistry since the discovery of N-confused porphyrin, a porphyrin mutant, in 1994. These days, the…
Nucleophilic Aromatic Substitution (SNAr) and Related Reactions of Porphyrinoids: Mechanistic and Regiochemical Aspects
TLDR
The use of nucleophilic substitution on porphyrinoids is found to often be a cost‐effective procedure with the ability to yield complex substituent patterns, which can be conducted in non‐anhydrous solvents with easily accessible simple porphirinoids.
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TLDR
The distinctive macrocyclic environment creates a long-sought opportunity to trap unique organometallic transformations which include instances of benzene ring contraction to cyclopentadiene or the formation of an unprecedented metalloporphyrinoid: 21-pallada-23-telluraporphyrin.
Theoretical study on the conformation and aromaticity of regular and singly N-confused [28]hexaphyrins.
TLDR
Structures and electronic states of regular and singly N-confused [28]hexaphyrins were thoroughly studied with the aid of DFT calculations and interconversion pathways among conformers were proposed on the basis of calculations on singlyN-conf confused [28], causing weakening of both aromatic and antiaromatic characteristics.
Crossed and Linked Histories of Tetrapyrrolic Macrocycles and Their Use for Engineering Pores within Sol-Gel Matrices
TLDR
The result would confirm again that tetrapyrrolic macrocycles can help in the development of the authentic pore engineering in materials science and support the prospect of tuning up the pore size, surface area, and polarity inside the por cavities in order to prepare efficient catalytic, optical, sensoring, and medical systems.
Porphyrin derivatives and mRNA alternative splicing induced by photodynamic therapy
In this work the synthesis of regular and Nconfused porphyrins with the objective of assessing its efficiency as photosensitizers (PSs) in photodynamic therapy (PDT) and its influence in alternative…
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