Strained porphyrin tape-cycloparaphenylene hybrid nanorings
Strained porphyrin tape-cycloparaphenylene hybrid nanorings
V-Shaped porphyrin dimers, with masked p-phenylene bridges, undergo efficient oxidative coupling to form meso-meso linked cyclic porphyrin oligomers. Reductive aromatization unmasks the p-phenylenes, increasing the strain. Oxidation then fuses the porphyrin dimers, providing a nanoring with curved walls. The strain in this macrocycle bends the p-phenylene and fused porphyrin dimer units (radii of curvature of 11.4 and 19.0 Å, respectively), but it does not significantly alter the electronic structure of the fused porphyrins.
378-383
Stawski, Wojciech
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Van Raden, Jeff M.
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Patrick, Connor W.
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Horton, Peter N.
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Coles, Simon J.
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Anderson, Harry L.
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20 January 2023
Stawski, Wojciech
f48b1ec5-f759-44e5-8dbc-de123f25d074
Van Raden, Jeff M.
fb3055d8-9245-4458-848b-c920e90aaeba
Patrick, Connor W.
f370cc86-acef-4291-91de-ed24d2f3bd5a
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Anderson, Harry L.
30cdcaf7-e460-409f-b9c3-96ded4744081
Stawski, Wojciech, Van Raden, Jeff M., Patrick, Connor W., Horton, Peter N., Coles, Simon J. and Anderson, Harry L.
(2023)
Strained porphyrin tape-cycloparaphenylene hybrid nanorings.
Organic Letters, 25 (2), .
(doi:10.1021/acs.orglett.2c04089).
Abstract
V-Shaped porphyrin dimers, with masked p-phenylene bridges, undergo efficient oxidative coupling to form meso-meso linked cyclic porphyrin oligomers. Reductive aromatization unmasks the p-phenylenes, increasing the strain. Oxidation then fuses the porphyrin dimers, providing a nanoring with curved walls. The strain in this macrocycle bends the p-phenylene and fused porphyrin dimer units (radii of curvature of 11.4 and 19.0 Å, respectively), but it does not significantly alter the electronic structure of the fused porphyrins.
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acs.orglett.2c04089
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e-pub ahead of print date: 10 January 2023
Published date: 20 January 2023
Additional Information:
Funding Information:
The authors thank the ERC (Grant 885606, ARO-MAT) and EPSRC (Grant EP/N017188/1) for funding and Oxford Advanced Research Computing (ARC) for computational resources ( 10.5281/zenodo.22558 ).
Identifiers
Local EPrints ID: 475523
URI: http://eprints.soton.ac.uk/id/eprint/475523
ISSN: 1523-7060
PURE UUID: d4101558-164a-4c49-937c-14143d61a9ca
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Date deposited: 21 Mar 2023 17:35
Last modified: 18 Mar 2024 02:51
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Contributors
Author:
Wojciech Stawski
Author:
Jeff M. Van Raden
Author:
Connor W. Patrick
Author:
Peter N. Horton
Author:
Harry L. Anderson
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