» Articles » PMID: 35539959

Heterocorroles: Corrole Analogues Containing Heteroatom(s) in the Core or at a -position

Overview
Journal RSC Adv
Specialty Chemistry
Date 2022 May 11
PMID 35539959
Authors
Affiliations
Soon will be listed here.
Abstract

Corroles are 18 π aromatic macrocyclic systems having one direct pyrrole-pyrrole linkage leading to a contracted cavity compared to porphyrins. Corroles exhibit contrasting coordination chemistry and properties compared to porphyrins. Structural modification of corroles by introducing a heteroatom in their aromatic conjugation circuit , either in the core or at a position leads to a new class of corrinoids called heterocorroles. The core modification strategy includes replacing one or two core nitrogen atom(s) with O, S or C atoms and -modification involves replacing the -carbon atom at the 10-position with NH, NR, O, S, Se or Si atoms. This review article presents an overview of the progress in heterocorrole chemistry including their syntheses, key structural aspects and properties.

Citing Articles

Metallaantiaromaticity of 10-Platinacorrole Complexes.

Miwa K, Yokota T, Wang Q, Sakurai T, Fliegl H, Sundholm D J Am Chem Soc. 2024; 146(2):1396-1402.

PMID: 38172072 PMC: 10882971. DOI: 10.1021/jacs.3c10250.


Luminescence and Palladium: The Odd Couple.

Dalmau D, Urriolabeitia E Molecules. 2023; 28(6).

PMID: 36985639 PMC: 10054068. DOI: 10.3390/molecules28062663.


The Selective Monobromination of a Highly Sterically Encumbered Corrole: Structural and Spectroscopic Properties of Fe(Cl)(2-Bromo-5,10,15-tris(triphenyl)phenyl corrole).

Alvarado J, Cummins D, Diaconescu A, Siegler M, Goldberg D J Porphyr Phthalocyanines. 2022; 25(10-12):1176-1185.

PMID: 36213143 PMC: 9536772. DOI: 10.1142/s1088424621501169.


Magnetic Diversity in Heteroisocorroles: Aromatic Pathways in 10-Heteroatom-Substituted Isocorroles.

Foroutan-Nejad C, Ghosh A ACS Omega. 2019; 3(11):15865-15869.

PMID: 31458232 PMC: 6643806. DOI: 10.1021/acsomega.8b02626.

References
1.
Ghosh A, Chatterjee T, Lee W, Ravikanth M . Unusual formation of 21-oxacorrole from 21-oxaporphyrin induced by phosphoryl chloride. Org Lett. 2013; 15(5):1040-3. DOI: 10.1021/ol303527v. View

2.
Sankar J, Rath H, Prabhuraja V, Chandrashekar T, Vittal J . Syntheses of core-modified corroles by three different [3 + 1] methodologies. J Org Chem. 2004; 69(15):5135-8. DOI: 10.1021/jo0497398. View

3.
Sankar J, Rath H, Prabhuraja V, Gokulnath S, Chandrashekar T, Purohit C . meso-meso-Linked corrole dimers with modified cores: synthesis, characterization, and properties. Chemistry. 2006; 13(1):105-14. DOI: 10.1002/chem.200600457. View

4.
Sakow D, Baabe D, Boker B, Burghaus O, Funk M, Kleeberg C . Iron 10-thiacorroles: bioinspired iron(III) complexes with an intermediate spin (S=3/2) ground state. Chemistry. 2014; 20(10):2913-24. DOI: 10.1002/chem.201303786. View

5.
Aviv-Harel I, Gross Z . Aura of corroles. Chemistry. 2009; 15(34):8382-8394. DOI: 10.1002/chem.200900920. View