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Synthesis and molecular structure of a copper octaiodocorrole

Synthesis and molecular structure of a copper octaiodocorrole
Synthesis and molecular structure of a copper octaiodocorrole

Although rather delicate on account of their propensity to undergo deiodination, β-octaiodoporphyrinoids are of considerable interest as potential precursors to novel β-octasubstituted macrocycles. Presented herein are early results of our efforts to synthesize β-octaiodocorrole derivatives. Oxidative condensation of 3,4-diiodopyrrole and aromatic aldehydes failed to yield free-base octaiodocorroles. Treatment of copper meso-tris(p-cyanophenyl)corrole with N-iodosuccinimide and trifluoroacetic acid over several hours, however, yielded the desired β-octaiodinated product in ∼22% yield. Single-crystal X-ray structure determination of the product revealed a strongly saddled corrole macrocycle with metrical parameters very close to those of analogous Cu octabromocorrole complexes. The compound was also found to exhibit an exceptionally red-shifted Soret maximum (464 nm in dichloromethane), underscoring the remarkable electronic effect of β-octaiodo substitution.

2470-1343
5106-5110
Thomassen, Ivar K.
c2d0503b-d24b-4eb6-ba83-5204ec3d7c78
Mccormick, Laura J.
f1c2f8cd-adcc-4bbf-9289-0b33a006d2bb
Ghosh, Abhik
01a311da-a139-43f0-ae29-0efa0e8788f7
Thomassen, Ivar K.
c2d0503b-d24b-4eb6-ba83-5204ec3d7c78
Mccormick, Laura J.
f1c2f8cd-adcc-4bbf-9289-0b33a006d2bb
Ghosh, Abhik
01a311da-a139-43f0-ae29-0efa0e8788f7

Thomassen, Ivar K., Mccormick, Laura J. and Ghosh, Abhik (2018) Synthesis and molecular structure of a copper octaiodocorrole. ACS Omega, 3 (5), 5106-5110. (doi:10.1021/acsomega.8b00616).

Record type: Article

Abstract

Although rather delicate on account of their propensity to undergo deiodination, β-octaiodoporphyrinoids are of considerable interest as potential precursors to novel β-octasubstituted macrocycles. Presented herein are early results of our efforts to synthesize β-octaiodocorrole derivatives. Oxidative condensation of 3,4-diiodopyrrole and aromatic aldehydes failed to yield free-base octaiodocorroles. Treatment of copper meso-tris(p-cyanophenyl)corrole with N-iodosuccinimide and trifluoroacetic acid over several hours, however, yielded the desired β-octaiodinated product in ∼22% yield. Single-crystal X-ray structure determination of the product revealed a strongly saddled corrole macrocycle with metrical parameters very close to those of analogous Cu octabromocorrole complexes. The compound was also found to exhibit an exceptionally red-shifted Soret maximum (464 nm in dichloromethane), underscoring the remarkable electronic effect of β-octaiodo substitution.

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Published date: 9 May 2018

Identifiers

Local EPrints ID: 438918
URI: http://eprints.soton.ac.uk/id/eprint/438918
ISSN: 2470-1343
PURE UUID: e5a12734-f0e5-481c-b4c2-406cf81bde4b
ORCID for Laura J. Mccormick: ORCID iD orcid.org/0000-0002-6634-4717

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Date deposited: 26 Mar 2020 17:35
Last modified: 07 Oct 2020 02:27

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Contributors

Author: Ivar K. Thomassen
Author: Abhik Ghosh

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