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Rapid one-pot synthesis of pyrrole-appended isocorroles

Rapid one-pot synthesis of pyrrole-appended isocorroles
Rapid one-pot synthesis of pyrrole-appended isocorroles

Free-base meso-triarylcorroles have been found to undergo oxidative coupling with an excess of pyrrole in dichloromethane in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) affording 5/10-pyrrole-appended isocorroles in reasonable yields (35-60%) and in a matter of seconds. The free-base isocorrole ligands could all be complexed to copper with Cu(OAc)2·H2O in chloroform/methanol in 55-80% yields. Single-crystal X-ray structures of two of the new compounds (H2[5-pyr-TpOMePiC] and Cu[10-pyr-TpOMePiC]) revealed planar macrocycles with rms atomic displacements of only 0.02 and 0.06 Å relative to their respective best-fit C19N4 planes. Both free-base and Cu(ii)-complexed isocorroles exhibit richly featured UV-vis-NIR spectra with red/NIR absorption maxima at ∼650 nm and ∼725 nm for the free-bases and ∼800-850 nm for the copper complexes, suggesting potential applications in photodynamic therapy. Cyclic voltammetric analyses of five of the Cu complexes revealed fully reversible redox cycles with multiple oxidation and reduction features.

1477-0520
3159-3166
Larsen, Simon
8b33a5ee-852e-4209-91d8-324b91ea02d1
McCormick, Laura J.
f1c2f8cd-adcc-4bbf-9289-0b33a006d2bb
Ghosh, Abhik
01a311da-a139-43f0-ae29-0efa0e8788f7
Larsen, Simon
8b33a5ee-852e-4209-91d8-324b91ea02d1
McCormick, Laura J.
f1c2f8cd-adcc-4bbf-9289-0b33a006d2bb
Ghosh, Abhik
01a311da-a139-43f0-ae29-0efa0e8788f7

Larsen, Simon, McCormick, Laura J. and Ghosh, Abhik (2019) Rapid one-pot synthesis of pyrrole-appended isocorroles. Organic and Biomolecular Chemistry, 17 (12), 3159-3166. (doi:10.1039/c9ob00168a).

Record type: Article

Abstract

Free-base meso-triarylcorroles have been found to undergo oxidative coupling with an excess of pyrrole in dichloromethane in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) affording 5/10-pyrrole-appended isocorroles in reasonable yields (35-60%) and in a matter of seconds. The free-base isocorrole ligands could all be complexed to copper with Cu(OAc)2·H2O in chloroform/methanol in 55-80% yields. Single-crystal X-ray structures of two of the new compounds (H2[5-pyr-TpOMePiC] and Cu[10-pyr-TpOMePiC]) revealed planar macrocycles with rms atomic displacements of only 0.02 and 0.06 Å relative to their respective best-fit C19N4 planes. Both free-base and Cu(ii)-complexed isocorroles exhibit richly featured UV-vis-NIR spectra with red/NIR absorption maxima at ∼650 nm and ∼725 nm for the free-bases and ∼800-850 nm for the copper complexes, suggesting potential applications in photodynamic therapy. Cyclic voltammetric analyses of five of the Cu complexes revealed fully reversible redox cycles with multiple oxidation and reduction features.

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More information

Accepted/In Press date: 26 February 2019
e-pub ahead of print date: 6 March 2019

Identifiers

Local EPrints ID: 438799
URI: http://eprints.soton.ac.uk/id/eprint/438799
ISSN: 1477-0520
PURE UUID: 544c6f4d-79f2-4e21-89e7-6bd3f43e6a40
ORCID for Laura J. McCormick: ORCID iD orcid.org/0000-0002-6634-4717

Catalogue record

Date deposited: 24 Mar 2020 17:52
Last modified: 07 Oct 2020 02:27

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Contributors

Author: Simon Larsen
Author: Abhik Ghosh

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