Molecular Engineering of Free‐Base Porphyrins as Ligands—The N−H⋅⋅⋅X Binding Motif in Tetrapyrroles
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- Marc Kielmann
- School of Chemistry SFI Tetrapyrrole Laboratory Trinity Biomedical Sciences Institute Trinity College Dublin The University of Dublin 152–160 Pearse Street Dublin 2 Ireland
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- Mathias O. Senge
- School of Chemistry SFI Tetrapyrrole Laboratory Trinity Biomedical Sciences Institute Trinity College Dublin The University of Dublin 152–160 Pearse Street Dublin 2 Ireland
書誌事項
- 公開日
- 2018-11-05
- 権利情報
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- http://creativecommons.org/licenses/by-nc/4.0/
- DOI
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- 10.1002/anie.201806281
- 公開者
- Wiley
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説明
<jats:title>Abstract</jats:title><jats:p>The core N−H units of planar porphyrins are often inaccessible to forming hydrogen‐bonding complexes with acceptor molecules. This is due to the fact that the amine moieties are “shielded” by the macrocyclic system, impeding the formation of intermolecular H‐bonds. However, methods exist to modulate the tetrapyrrole conformations and to reshape the vector of N−H orientation outwards, thus increasing their availability and reactivity. Strategies include the use of porpho(di)methenes and phlorins (calixphyrins), as well as saddle‐distorted porphyrins. The former form cavities due to interruption of the aromatic system. The latter are highly basic systems and capable of binding anions and neutral molecules via N−H⋅⋅⋅X‐type H‐bonds. This Review discusses the role of porphyrin(oid) ligands in various coordination‐type complexes, means to access the core for hydrogen bonding, the concept of conformational control, and emerging applications, such as organocatalysis and sensors.</jats:p>
収録刊行物
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- Angewandte Chemie International Edition
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Angewandte Chemie International Edition 58 (2), 418-441, 2018-11-05
Wiley
